10-Q

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

___________________________________________________________________________________________

Form 10-Q

☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d)

OF THE SECURITIES EXCHANGE ACT OF 1934

For the quarterly period ended September 30, 2020

OR

☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d)

OF THE SECURITIES EXCHANGE ACT OF 1934

Commission file number 001-38731

___________________________________________________________________________________________

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

(Exact name of registrant as specified in its charter)

Bermuda

(State or other jurisdiction of incorporation or organization)

98-0529995

(I.R.S. Employer Identification No.)

14 Wesley Street, Hamilton HM 11, Bermuda

(Address of principal executive offices)

(441) 278-3140

(Registrant's telephone number, including area code)

___________________________________________________________________________________________

Securities registered pursuant to Section 12(b) of the Act:

Title of each class	Trading symbol	Name of each exchange on which registered
Common shares, par value $0.01 per share	SG	Nasdaq Global Select Market

Indicate by check mark whether the registrant: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of "large accelerated filer," "accelerated filer," "smaller reporting company," and "emerging growth company" in Rule 12b-2 of the Exchange Act.

Large accelerated filer ☐  Accelerated filer ☐  Non-accelerated filer ☒  Smaller reporting company ☒  Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐    No ☒

At October 31, 2020, there were 115,299,341 Common Shares, $0.01 par value per share, of the registrant outstanding.

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

INDEX TO FORM 10-Q

		Page
Part I	Financial Information	1
	Cautionary Note Regarding Forward-Looking Statements	1
Item 1.	Unaudited Consolidated Financial Statements	3
	Consolidated Balance Sheets at September 30, 2020 and December 31, 2019	3
	Consolidated Statement of Income for the three and nine months ended September 30, 2020 and 2019	4
	Consolidated Statements of Comprehensive Income for the three and nine months ended September 30, 2020 and 2019	5
	Consolidated Statements of Shareholders' Equity for the three and nine months ended September 30, 2020 and 2019	6
	Consolidated Statements of Cash Flows for the three and nine months ended September 30, 2020 and 2019	7
	Notes to Consolidated Financial Statements	8
Item 2.	Management's Discussion and Analysis of Financial Condition and Results of Operations	50
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	86
Item 4.	Controls and Procedures	86
Part II	Other Information	87
Item 1.	Legal Proceedings	87
Item 1A.	Risk Factors	87
Item 2.	Unregistered Sales of Equity Securities and Use of Proceeds	93
Item 3.	Defaults Upon Senior Securities	93
Item 4.	Mine Safety Disclosures	93
Item 5.	Other Information	93
Item 6.	Exhibits	94
	Signatures	95

PART I. FINANCIAL INFORMATION

Cautionary Note Regarding Forward-Looking Statements

This Quarterly Report on Form 10-Q contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934, including statements about the future financial condition, results of operations and operating activities of Sirius International Insurance Group, Ltd. (the "Company" and, together with its subsidiaries, "Sirius Group"), including impacts of the COVID-19 pandemic on its business, operations and loss reserve estimates. Forward-looking statements are typically identified by words such as "plan," "believe," "expect," "anticipate," "intend," "outlook," "estimate," "forecast," "project," "target," "continue," "could," "may," "might," "will," "possible," "potential," "predict," "should," "would," "seeks," "likely" and other similar words and expressions, but the absence of these words does not mean that a statement is not forward-looking. The forward-looking statements are based on the current expectations of the management of the Company and speak only as of the date of this Quarterly Report on Form 10-Q. There can be no assurance that future developments will be those that have been anticipated. These forward-looking statements involve a number of risks, uncertainties or other assumptions that may cause actual results or performance to be materially different from those expressed or implied by these forward-looking statements. These risks and uncertainties include, but are not limited to, the following:

•the continued impact of the COVID-19 pandemic on Sirius Group’s business, operations and loss reserve estimates;

•the effect of judicial, legislative and regulatory actions to address and contain the impact of COVID-19;

•the uncertainty as to the estimate of ultimate industry loss claims;

•the general economic conditions and market conditions in the markets in which Sirius Group operates;

•Sirius Group's exposure to unpredictable catastrophic and casualty events and unexpected accumulations of attritional losses;

•increased competition from existing insurers and reinsurers and from alternative capital providers, such as insurance-linked funds and collateralized special purpose insurers;

•decreased demand for Sirius Group's insurance or reinsurance products, consolidation and cyclical changes in the insurance and reinsurance industry;

•the inherent uncertainty of estimating loss and loss adjustment expenses reserves, including asbestos and environmental reserves, and the possibility that such reserves may be inadequate to cover Sirius Group's ultimate liability for losses;

•a decline in or withdrawal of Sirius Group's operating subsidiaries' ratings with rating agencies;

•the exposure of Sirius Group's investments to interest rate, credit, equity risks and market volatility, which may limit Sirius Group's net income and may affect the adequacy of its capital and liquidity;

•losses related to cyber-attacks on Sirius Group's information technology systems;

•the impact of various risks associated with transacting business in foreign countries, including foreign currency exchange-rate risk and political risks on investments in, and revenues from, Sirius Group's operations outside the U.S.;

•the possibility that Sirius Group may become subject to additional onerous governmental or regulatory requirements or fail to comply with applicable regulatory and solvency requirements;

•Sirius Group's significant deferred tax assets may become materially impaired as a result of insufficient taxable income or a reduction in applicable corporate tax rates or other change in applicable tax law;

•a decrease in the fair value of Global A&H and/or Sirius Group's intangible assets may result in future impairments;

•the limited liquidity and trading of the Company's securities;

1

•China Minsheng Investment Group Corp., Ltd. ("CMIG") and CMIG International Holding Pte. Ltd.'s status as indirect and direct majority shareholders, including their affiliates' liquidity issues, and actions taken by CMIG, CMIG International Holding Pte. Ltd. or any other parties in interest in connection with such liquidity issues including ownership changes;

•Sirius Group's status as a publicly traded company, foreign private issuer and controlled company;

•the consequences of the written resolution of Sirius Group's majority shareholder which may prohibit the Board of Sirius Group from issuing any form of equity without shareholder approval;

•the impact of lawsuits initiated by minority shareholders, including lawsuits claiming that they are being unfairly oppressed by Sirius Group’s majority shareholder or lawsuits claiming a right of redemption of the Series B preference shares;

•the satisfaction or waiver of the conditions precedent to the consummation of the proposed transactions described in an Agreement and Plan of Merger entered into by and among the Company, Third Point Reinsurance Ltd.("TPRE") and Yoga Merger Sub Limited dated August 6, 2020 and the terms and conditions included in a statutory merger agreement (collectively, the "Transactions"), including, without limitation, the receipt of shareholder and regulatory approvals (including approvals, authorizations and clearance by antitrust authorities and insurance regulators necessary to complete such proposed Transactions) on the terms desired or anticipated (and the risk that such approvals may result in the imposition of conditions that could adversely affect the combined company or the expected benefits of such proposed Transactions);

•unanticipated difficulties or expenditures relating to such proposed Transactions;

•risks relating to the value of the shares of TPRE to be issued in such proposed Transactions;

•unanticipated negative reactions of rating agencies in response to such proposed Transactions;

•disruptions of the Company’s and TPRE’s current plans, operations and relationships with third persons caused by the announcement and pendency of such proposed Transactions, including, without limitation, the ability of the combined company to hire and retain any personnel;

•legal proceedings that may be instituted against the Company and TPRE following announcement of such proposed Transactions; and

•other risks identified elsewhere in this Quarterly Report on Form 10-Q, the Company's Annual Report on Form 10-K for the year ended December 31, 2019 and in the Company's other filings with the U.S. Securities and Exchange Commission.

Should one or more of these risks or uncertainties materialize, or should any of the assumptions made by the management of the Company prove incorrect, actual results may vary in material respects from those projected in these forward-looking statements. Except to the extent required by applicable law or regulation, Sirius Group undertakes no obligation to update these forward-looking statements to reflect events or circumstances after the date of this Quarterly Report on Form 10-Q.

2

ITEM 1. CONSOLIDATED FINANCIAL STATEMENTS

Sirius International Insurance Group, Ltd.

Consolidated Balance Sheets

As at September 30, 2020 and December 31, 2019

(Expressed in millions of U.S. dollars, except share information)	September 30, 2020		December 31, 2019
	Unaudited
Assets
Fixed maturity investments, trading, at fair value (Amortized cost 2020: $1,932.7; 2019: $1,656.6)	$	1,958.9	$	1,681.0
Short-term investments, at fair value (Amortized cost 2020: $1,145.4; 2019: $1,090.8)	1,132.6		1,085.2
Equity securities, trading, at fair value (Cost 2020: $170.0; 2019: $379.2)	158.7		405.2
Other long-term investments, at fair value (Cost 2020: $327.5; 2019: $315.4)	388.0		346.8
Cash	168.4		136.3
Restricted cash	15.8		14.3
Total investments and cash	3,822.4		3,668.8
Accrued investment income	8.9		11.2
Insurance and reinsurance premiums receivable	789.0		730.1
Reinsurance recoverable on unpaid losses	482.5		410.3
Reinsurance recoverable on paid losses	70.4		73.9
Funds held by ceding companies	244.1		293.9
Ceded unearned insurance and reinsurance premiums	172.5		162.0
Deferred acquisition costs	145.2		148.2
Deferred tax asset	158.4		166.7
Accounts receivable on unsettled investment sales	19.1		6.7
Goodwill	400.8		400.8
Intangible assets	168.0		179.8
Other assets	151.5		161.4
Total assets	$	6,632.8	$	6,413.8
Liabilities
Loss and loss adjustment expense reserves	$	2,672.9	$	2,331.5
Unearned insurance and reinsurance premiums	759.4		708.0
Ceded reinsurance payable	270.3		244.7
Funds held under reinsurance treaties	156.5		169.1
Deferred tax liability	213.6		205.9
Debt	695.8		685.2
Accounts payable on unsettled investment purchases	29.9		2.3
Other liabilities	175.9		201.3
Total liabilities	4,974.3		4,548.0
Commitments and contingencies (see Note 19)
Mezzanine equity
Series B preference shares	197.5		223.0
Common shareholders' equity
Common shares (shares issued and outstanding, 2020 & 2019: 115,299,341)	1.2		1.2
Additional paid-in surplus	1,099.9		1,098.2
Retained earnings	564.5		778.5
Accumulated other comprehensive (loss)	(206.4)		(237.5)
Total common shareholders' equity	1,459.2		1,640.4
Non-controlling interests	1.8		2.4
Total equity	1,461.0		1,642.8
Total liabilities, mezzanine equity, and equity	$	6,632.8	$	6,413.8

See Notes to Consolidated Financial Statements

3

Sirius International Insurance Group, Ltd.

Consolidated Statements of (Loss) Income

For the three and nine months ended September 30, 2020 and 2019

Unaudited

	Three months ended September 30,				Nine months ended September 30,
(Expressed in millions of U.S. dollars, except share and per share information)	2020		2019		2020		2019
Revenues
Net earned insurance and reinsurance premiums	$	372.6	$	374.2	$	1,177.1	$	1,056.8
Net investment income	1.7		22.8		30.0		67.3
Net realized investment (losses) gains	(3.8)		15.3		23.6		39.9
Net unrealized investment gains (losses)	31.2		53.9		(3.9)		143.4
Net foreign exchange (losses) gains	(21.3)		4.9		(18.9)		9.4
Other revenue	15.8		16.3		30.3		51.3
Total revenues	396.2		487.4		1,238.2		1,368.1
Expenses
Loss and loss adjustment expenses	305.4		348.6		972.8		810.5
Insurance and reinsurance acquisition expenses	83.6		75.1		236.4		215.4
Other underwriting expenses	41.3		35.4		115.6		106.2
General and administrative expenses	34.4		28.0		90.4		80.6
Intangible asset amortization expenses	3.9		3.9		11.8		11.8
Interest expense on debt	8.1		7.7		23.8		23.3
Total expenses	476.7		498.7		1,450.8		1,247.8
Pre-tax income (loss)	(80.5)		(11.3)		(212.6)		120.3
Income tax (expense) benefit	(23.5)		3.7		(19.9)		(15.6)
Net (loss) income	(104.0)		(7.6)		(232.5)		104.7
(Income) attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
(Loss) income attributable to Sirius Group	(104.2)		(8.0)		(232.7)		103.1
Change in carrying value of Series B preference shares	8.7		5.3		25.5		(3.9)
Net (loss) income attributable to Sirius Group's common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	99.2
Net (loss) income per common share and common share equivalent
Basic earnings per common share and common share equivalent	$	(0.83)	$	(0.02)	$	(1.80)	$	0.78
Diluted earnings per common share and common share equivalent	$	(0.83)	$	(0.06)	$	(1.83)	$	0.78
Weighted average number of common shares and common share equivalents outstanding:
Basic weighted average number of common shares and common share equivalents outstanding	115,297,945		115,251,853		115,279,197		115,225,942
Diluted weighted average number of common shares and common share equivalents outstanding	115,297,945		127,153,523		127,180,867		115,619,222

See Notes to Consolidated Financial Statements

4

Sirius International Insurance Group, Ltd.

Consolidated Statements of Comprehensive (Loss) Income

For the three and nine months ended September 30, 2020 and 2019

Unaudited

	Three months ended September 30,				Nine months ended September 30,
(Expressed in millions of U.S. dollars)	2020		2019		2020		2019
Comprehensive (loss) income
Net (loss) income	$	(104.0)	$	(7.6)	$	(232.5)	$	104.7
Other comprehensive income (loss)
Change in foreign currency translation, net of tax	37.5		(42.3)		31.1		(69.0)
Total other comprehensive income (loss)	37.5		(42.3)		31.1		(69.0)
Comprehensive (loss) income	(66.5)		(49.9)		(201.4)		35.7
Net (income) attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
Comprehensive (loss) income attributable to Sirius Group	$	(66.7)	$	(50.3)	$	(201.6)	$	34.1

See Notes to Consolidated Financial Statements

5

Sirius International Insurance Group, Ltd.

Consolidated Statements of Shareholders' Equity

For the three and nine months ended September 30, 2020 and 2019

Unaudited

	Three months ended September 30,				Nine months ended September 30,
(Expressed in millions of U.S. dollars)	2020		2019		2020		2019
Common shares
Balance at beginning and end of period	$	1.2	$	1.2	$	1.2	$	1.2
Additional paid-in surplus
Balance at beginning of period	1,102.4		1,093.5		1,098.2		1,089.1
Share-based compensation	(2.5)		3.4		1.7		7.9
Other, net	—		0.1		—		—
Balance at end of period	1,099.9		1,097.0		1,099.9		1,097.0
Retained earnings
Balance at beginning of period	660.0		918.5		778.5		816.6
Cumulative effect of an accounting change	—		—		(6.8)		—
Balance at beginning of period, as adjusted	660.0		918.5		771.7		816.6
Net (loss) income	(104.0)		(7.6)		(232.5)		104.7
Loss (income) attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
Change in carrying value of Series B preference shares	8.7		5.3		25.5		(3.9)
Balance at end of period	564.5		915.8		564.5		915.8
Accumulated other comprehensive (loss)
Balance at beginning of period	(243.9)		(229.1)		(237.5)		(202.4)
Accumulated net foreign currency translation (losses)
Balance at beginning of period	(243.9)		(229.1)		(237.5)		(202.4)
Net change in foreign currency translation	37.5		(42.3)		31.1		(69.0)
Balance at the end of period	(206.4)		(271.4)		(206.4)		(271.4)
Balance at the end of period	(206.4)		(271.4)		(206.4)		(271.4)
Total common shareholders' equity	$	1,459.2	$	1,742.6	$	1,459.2	$	1,742.6
Non-controlling interests	1.8		3.4		1.8		3.4
Total equity	$	1,461.0	$	1,746.0	$	1,461.0	$	1,746.0

See Notes to Consolidated Financial Statements

6

Sirius International Insurance Group, Ltd.

Consolidated Statements of Cash Flows

For the nine months ended September 30, 2020 and 2019

Unaudited

	Nine months ended September 30,
(Expressed in millions of U.S. dollars)	2020		2019
Cash flows from operating activities:
Net (loss) income	$	(232.5)	$	104.7
Adjustments to reconcile net income to net cash provided from operations:
Net realized and unrealized investment losses (gains)	(19.7)		(183.3)
Amortization of premium on fixed maturity investments	3.8		(4.7)
Amortization of intangible assets	11.8		11.8
Depreciation and other amortization	5.0		6.3
Share-based compensation	1.7		7.9
Revaluation of contingent consideration	0.6		—
Net gain on sale of consolidated affiliate	(0.9)		—
Other operating items:
Net change in loss and loss adjustment expense reserves	296.8		274.1
Net change in reinsurance recoverable on paid and unpaid losses	(46.1)		(82.0)
Net change in funds held by ceding companies	54.3		(61.5)
Net change in unearned insurance and reinsurance premiums	24.0		212.4
Net change in ceded reinsurance payable	9.7		73.3
Net change in ceded unearned insurance and reinsurance premiums	0.5		(32.4)
Net change in insurance and reinsurance premiums receivable	(30.7)		(269.4)
Net change in deferred acquisition costs	6.4		(22.5)
Net change in funds held under reinsurance treaties	(15.7)		33.1
Net change in current and deferred income taxes, net	21.1		(4.8)
Net change in other assets and liabilities, net	25.4		24.9
Net cash provided from operating activities	115.5		87.9
Cash flows from investing activities:
Net change in short-term investments	(5.5)		(285.8)
Sales of fixed maturities and convertible fixed maturity investments	380.6		430.7
Maturities, calls, and paydowns of fixed maturity and convertible fixed maturity investments	223.5		239.4
Sales of common equity securities	858.5		212.6
Distributions, redemptions, and maturities of other long-term investments	22.8		53.6
Return of principal on loan participations	1.4		—
Sale of consolidated affiliate, net of cash sold	11.2		—
Contributions to other long-term investments	(30.5)		(46.5)
Purchases of common equity securities	(653.3)		(174.9)
Purchases of fixed maturities and convertible fixed maturity investments	(870.2)		(504.4)
Purchases of loan participation	(10.0)		—
Net change in unsettled investment purchases and sales	15.4		23.7
Other, net	(2.5)		0.8
Net cash (used for) investing activities	(58.6)		(50.8)
Cash flows from financing activities:
Payment of contingent consideration	(28.4)		—
Cash dividends paid to non-controlling interests	(1.0)		—
Change in collateral held on Interest Rate Cap	—		(0.1)
Net cash (used for) financing activities	(29.4)		(0.1)
Effect of exchange rate changes on cash	6.1		(9.4)
Net increase (decrease) in cash during period	33.6		27.6
Cash, restricted cash, and cash held for sale balance at beginning of period	150.6		132.2
Cash, restricted cash, and cash held for sale balance at end of period	$	184.2	$	159.8

See Notes to Consolidated Financial Statements

7

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 1. General

Sirius International Insurance Group, Ltd. ("the Company") is a Bermuda exempted company that provides multi-line insurance and reinsurance on a worldwide basis through its subsidiaries (collectively with the Company, "Sirius Group").

Note 2. Summary of significant accounting policies

Basis of presentation

The accompanying Unaudited Consolidated Financial Statements at September 30, 2020, have been prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP") and the rules and regulations of the U.S. Securities and Exchange Commission ("SEC") for interim financial information. The accompanying Unaudited Consolidated Financial Statements present the consolidated results of operations, financial condition, and cash flows of the Company and its subsidiaries and those entities in which the Company has control and a majority economic interest as well as those variable interest entities ("VIEs") that meet the requirements for consolidation. All significant intercompany transactions have been eliminated in consolidation.

These Unaudited Consolidated Financial Statements do not include all disclosures normally included in annual financial statements prepared in accordance with GAAP and should be read in conjunction with the Audited Consolidated Financial Statements and the related notes for the year ended December 31, 2019. The consolidated financial information as of December 31, 2019 included herein has been derived from the Audited Consolidated Financial Statements as of December 31, 2019.

Effective January 1, 2020, the Company changed its reportable segments. The change in reportable segments had no impact on the Company’s historical consolidated financial positions, results of operations or cash flows as previously reported. Where applicable, all prior periods presented have been revised to conform to this new presentation.

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities as of the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. In the opinion of management, the accompanying Unaudited Consolidated Financial Statements reflect all adjustments (consisting of normally recurring accruals) necessary for a fair statement of results on an interim basis. Tabular dollar amounts are in millions, with the exception of share and per share amounts. All amounts are reported in U.S. dollars, except where noted otherwise.

Recently adopted changes in accounting principles

Credit losses

Effective January 1, 2020, Sirius Group adopted Accounting Standards Update ("ASU") 2016-13, Measurement of Credit Losses on Financial Instruments (ASC 326), which establishes new guidance for the recognition of credit losses for financial assets measured at amortized cost ("current expected credit losses" or "CECL"). The guidance applies to financial assets that have the contractual right to receive cash, including reinsurance receivables and recoverables and requires reporting entities to estimate the credit losses expected over the life of a credit exposure using historical information, current information and reasonable and supportable forecasts that affect the collectability of the financial asset. The expected credit losses, and subsequent adjustments to such losses, are recorded through an allowance account that is deducted from the amortized cost basis of the financial asset, with the net carrying value of the financial asset presented on the consolidated balance sheet at the amount expected to be collected. Sirius Group adopted the new guidance using a modified retrospective transition method through a cumulative-effect adjustment to retained earnings.

As a result of the adoption of the new guidance, Sirius Group estimated a total CECL allowance of $14.9 million. The adoption of this guidance did not materially impact our results of operations or cash flows. Due to the adoption of the standard using the retrospective cumulative-effect adjustment method, the Company recorded a $(6.8) million cumulative-effect adjustment net of taxes to its opening retained earnings. (See Note 7.)

8

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Fair Value Measurement Disclosures

Effective January 1, 2020, Sirius Group adopted ASU 2018-13, Fair Value Measurement (Topic 820): Disclosure Framework—Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements of fair value measurements. The adoption of this guidance did not have any impact on the consolidated financial statements but expanded disclosure of the ranges and weighted averages of significant unobservable inputs used in Level 3 fair values. (See Note 9.)

Simplifying the Accounting for Income Taxes

Effective January 1, 2020, Sirius Group adopted ASU 2019-12, Income Taxes (Topic 740): Simplifying the Accounting for Income Taxes, which eliminates certain exceptions, and clarifies and simplifies certain aspects of accounting for income taxes. Sirius Group has fully adopted all provisions of the guidance with consideration of the various transition methods.

Sirius Group adopted the removal of the exception to the general methodology for calculating income taxes in an interim period when a year-to-date loss exceeds the anticipated loss for the year. The removal of this exception allowed Sirius Group to record a benefit for a year-to-date loss in excess of its forecasted loss in certain jurisdictions. The removal of this exception was applied prospectively to the Income tax benefit (expense) line on the Consolidated Statements of (Loss) Income.

Sirius Group adopted all other provisions in the guidance, including the requirement for an entity to recognize a franchise tax (or similar tax) that is partially based on income as an income-based tax and account for any incremental amount incurred as a non-income-based tax through a cumulative-effect adjustment to retained earnings. These provisions did not have a material impact on the Consolidated Financial Statements or were not applicable to Sirius Group.

Note 3. Significant transactions

Merger Agreement with Third Point Reinsurance, Ltd.

On August 6, 2020, the Company announced that it had entered into an Agreement and Plan of Merger (the “Merger Agreement”), by and among the Company, Third Point Reinsurance Ltd., a Bermuda exempted company (“TPRE”), and Yoga Merger Sub Limited, a Bermuda exempted company and a wholly owned subsidiary of TPRE (“Merger Sub”). The Merger Agreement provides, among other things, that, upon the terms and subject to the conditions set forth in the Merger Agreement and a Statutory Merger Agreement to be executed by the Company, TPRE and Merger Sub (the “Statutory Merger Agreement”), Merger Sub will merge with and into the Company, with the Company surviving as a wholly owned subsidiary of TPRE (the “Merger”). The Merger Agreement, the Statutory Merger Agreement, and the consummation of the transactions contemplated by the Merger Agreement and the Statutory Merger Agreement, including the Merger (the “Transactions”), have been unanimously approved by the board of directors of each of the Company and TPRE. The consummation of the Transactions is expected to occur during the first quarter of 2021, subject to the satisfaction or waiver of applicable closing conditions.

9

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Under the terms of the Merger Agreement, as of the effective time of the Merger, each issued and outstanding common share, par value $0.01 per share, of the Company (“Company Shares”) will be converted into the right to receive, at the election of the holder thereof, (i) $9.50 in cash, or (ii) (A) 0.743 of a common share, par value $0.10 per share, of TPRE (“TPRE Shares”) and (B) one contractual contingent value right (each, a “CVR”), which will represent the right to receive a contingent cash payment, and which, taken together with the fraction of the TPRE Share received, guarantee that on the second anniversary of the closing date of the Merger, the electing shareholder will have received equity and cash with a value of at least $13.73 per share (the “Share & CVR Election”), or (iii) (A) $0.905 in cash, (B) a number of TPRE Shares equal to the Mixed Election Common Shares Exchange Ratio (as such term is defined in the Merger Agreement), (C) a number of newly issued Series A preference shares of TPRE (“TPRE Preference Shares”) equal to the Mixed Election Preference Shares Exchange Ratio (as such term is defined in the Merger Agreement), (D) 0.190 of a warrant issued by TPRE and (E) $0.905 aggregate principal amount of a right issued by TPRE (the “Mixed Election”). Elections must be made no later than ten (10) Business Days (as defined in the Merger Agreement) prior to the closing of the Transactions. Pursuant to the Voting and Support Agreement dated August 6, 2020 among CM Bermuda Limited ("CM Bermuda"), CMIG International Holding Pte. Ltd. (“CMIG International”), the Company and TPRE, CM Bermuda, whose parent company is CMIG International, has agreed to make the Mixed Election. Holders of Company Shares who do not make an election will be deemed to have made the Share & CVR Election. No fractional TPRE Shares or TPRE Preference Shares will be issued in the Merger, and holders of Company Shares will receive cash in lieu of any fractional TPRE Shares or TPRE Preference Shares. Dissenting Company shareholders will be entitled to exercise appraisal rights under Bermuda law.

The consummation of the Merger is subject to the satisfaction or waiver of certain conditions, including, among others, (i) the affirmative vote in favor of the approval of the Merger Agreement, the Merger and the Statutory Merger Agreement by the holders of a majority of the voting power of the Company Shares and the Company’s Series B preference shares, voting together as a single class, that are present (in person or by proxy) at the Company shareholder meeting called for such purpose, (ii) the affirmative vote in favor of the approval of the issuance of TPRE Shares in the Merger as contemplated by the Merger Agreement (the “TPRE Share Issuance”) by the holders of at least a majority of the voting power of TPRE Shares that are present (in person or by proxy) at the TPRE shareholder meeting called for such purpose, (iii) the expiration or termination of any applicable waiting period (together with any extensions thereof) under the Hart-Scott-Rodino Antitrust Improvements Act of 1976 and any other applicable antitrust laws, (iv) the receipt of certain approvals under applicable insurance laws, (v) the absence of any effective order issued by any governmental authority or court of competent jurisdiction or other legal restraint prohibiting or preventing the consummation of the Merger, (vi) in the case of each party’s obligation to effect the Merger, the absence of a material adverse effect with respect to the other party and its subsidiaries, taken as a whole, since the date of the Merger Agreement, (vii) in the case of each party’s obligation to effect the Merger, subject to certain materiality exceptions, the accuracy of the representations and warranties made by the other party, and compliance by the other party in all material respects with such party’s respective obligations under the Merger Agreement and (viii) other customary closing conditions.

Sirius Group incurred various legal, advisory, and other consulting costs associated with the proposed Merger of $10 million, which are included in the Company's financial condition or results of operations as of and for the three and nine months ended September 30, 2020. As part of the amount incurred, $2.2 million is in connection with the Transaction Matters Letter Agreement entered into by Sirius Group, TPRE, CM Bermuda and CMIG International on August 6, 2020. (See Note 18.)

Empire Insurance Company

On July 7, 2020, Sirius Group sold 100% of the common shares of Empire Insurance Company (“Empire”) to Physicians' Reciprocal Insurers. Sirius Group received $11.4 million of proceeds and recognized a $0.9 million gain on the sale of Empire.

Loss portfolio transfer

On January 23, 2020, Sirius Group consummated a loss portfolio transfer with Pacific Re, Inc. Under the agreement, Sirius Group received $69.7 million in cash and assumed net undiscounted loss and loss adjustment expenses ("LAE") reserves with the same value. In addition, Sirius Group recognized Gross written premium and Loss and loss adjustment expenses for $69.7 million.

As part of closing on the loss portfolio transfer, an estimate of net paid losses was included. Sixty days after the closing, actual net paid losses were determined and Sirius Group paid back $0.4 million in cash to Pacific Re, Inc. and reduced assumed net undiscounted loss and LAE reserves by the same value. In addition, Sirius Group adjusted Gross written premium and Loss and loss adjustment expenses by $(0.4) million.

10

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 4. Segment information

On December 31, 2019, Sirius Group completed an internal reorganization and, beginning on January 1, 2020, Sirius Group's reportable segments consist of four reportable segments – Global Reinsurance, Global Accident & Health ("Global A&H"), U.S. Specialty, and Runoff & Other. The accounting policies of the reportable segments are the same as those used for the preparation of the Company's consolidated financial statements.

The Company's Global Reinsurance, Global A&H, U.S. Specialty, and Runoff & Other reportable segments each have managers who are responsible for the overall profitability of their respective segments and who are directly accountable to the Company's chief operating decision maker, the Chief Executive Officer ("CEO") of the Company. The CEO assesses segment operating performance, allocates capital, and makes resource allocation decisions based on Technical income (loss), Underwriting income (loss), and Underwriting profit (loss), including net service fee revenue.

Segment results are shown prior to corporate eliminations. Corporate eliminations are shown to reconcile to consolidated Technical profit (loss), consolidated Underwriting income (loss) and consolidated Underwriting income (loss), including net service fee revenue.

Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets, and, accordingly, investment income is not allocated to each segment. The internal reorganization had no impact to the allocation of goodwill and intangible assets to the Global A&H segment. Where applicable, all prior periods presented have been revised to conform to this new presentation.

Global Reinsurance

Global Reinsurance consists of Sirius Group's underwriting lines of business that offer Other Property, Property Catastrophe Excess Reinsurance, Agriculture Reinsurance, Aviation & Space, Marine & Energy, Trade Credit, Contingency, and Casualty Reinsurance:

Other Property—Sirius Group participates in the broker market for property reinsurance treaties written on a proportional and excess of loss basis. For Sirius Group's international business, the book consists of treaty, written on both a proportional and excess of loss basis, facultative, and primary business, primarily in Europe, Asia and Latin America. In the United States, the book predominantly centers on significant participations on proportional and excess of loss treaties mostly in the excess and surplus lines segment of the market.

Property Catastrophe Excess Reinsurance—Property catastrophe excess of loss reinsurance treaties cover losses from catastrophic events. Sirius Group writes a worldwide book with the largest concentration of exposure in Europe and the United States. The U.S. book written in Bermuda has a national account focus supporting principally the lower and/or middle layers of large capacity programs. Additionally, Stockholm writes a U.S. book mainly consisting of select small regional and standard lines carriers. The exposures written in the international book are diversified across many countries, regions, perils and layers.

Agriculture Reinsurance—Sirius Group provides stop-loss reinsurance coverage to companies writing U.S. government-sponsored multi-peril crop insurance ("MPCI"). Sirius Group's participation is net of the government's stop-loss reinsurance protection. Sirius Group also provides coverage for crop-hail and certain named perils when bundled with MPCI business. Sirius Group also writes agriculture business outside of the United States.

Aviation & Space—Sirius Group provides aviation insurance that covers loss of or damage to an aircraft and the aircraft operations' liability to passengers, cargo and hull as well as to third parties. Additionally, liability arising out of non-aircraft operations such as hangars, airports and aircraft products can be covered. Space insurance primarily covers loss of or damage to a satellite during launch and in orbit. The book consists of treaty, written on both a proportional and excess of loss basis, facultative, and primary business.

Marine & Energy—Sirius Group provides marine & energy reinsurance, primarily written on an excess of loss and proportional basis. Coverage offered includes damage to ships and goods in transit, marine liability lines, and offshore energy industry insurance. Sirius Group also writes yacht business, both on reinsurance and a primary basis. The marine & energy portfolio is diversified across many countries and regions.

11

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Trade Credit—Sirius Group writes credit and bond reinsurance worldwide. The bulk of the business is traditional short-term commercial credit insurance, covering pre-agreed domestic and export sales of goods and services with typical coverage periods of 60 to 120 days. Losses under these policies are correlated to adverse changes in a respective country's gross national product.

Contingency—Sirius Group underwrote a contingency insurance book primarily for event cancellation and non-appearance.  Additionally, coverage for probability based risks with prize redemption was also offered. The contingency insurance business was exited in 2018; however, Sirius Group continues to offer this class on a treaty reinsurance basis on a selective basis for a few key clients.

Casualty Reinsurance—Sirius Group underwrites a cross section of all casualty lines, including general liability, umbrella, auto, workers compensation, professional liability, and other specialty classes, written on a proportional and excess of loss basis.

Global A&H

Global A&H consists of Sirius Group’s insurance and reinsurance business, and the managing general underwriting (“MGU”) units (which include ArmadaCorp Capital, LLC ("Armada") and International Medical Group, Inc. ("IMG")). Armada’s products are offered in the United States while IMG and the insurance and reinsurance business write accident and health products on a worldwide basis:

Accident and Health insurance and reinsurance—Sirius Group is an insurer of accident and health business in the United States and internationally, on either an admitted or surplus lines basis, as well as a reinsurer of medical expense, travel and personal accident on a treaty or facultative basis worldwide. The MGU unit writes health insurance business worldwide through IMG and within the United States via Armada.

U.S. Specialty

U.S. Specialty consists of Sirius Group's specialty insurance product offerings, which currently includes Environmental, Surety, and Workers’ Compensation.

Environmental underwrites a pure environmental insurance book in the United States consisting of four core products that revolve around pollution coverage, which are premises pollution liability, contractor's pollution liability, contractor's pollution and professional liability.

Surety underwrote commercial surety bonds, including non-construction contract bonds, in a broad range of business segments in the United States. In April 2020, the Company decided to exit the Surety business due to competitive market conditions in that business line and recent economic downturn which presented new risks and challenges for this line of business.

Workers' Compensation is a state-mandated insurance program that provides medical, disability, survivor, burial, and rehabilitation benefits to employees who are injured or killed due to a work-related injury or illness.

Runoff & Other

Runoff & Other includes the results of Sirius Global Solutions Holding Company ("Sirius Global Solutions"), which specializes in the acquisition and management of runoff liabilities for insurance and reinsurance companies, both in the United States and internationally, as well as asbestos risks, environmental risks and other long-tailed liability exposures.

12

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables summarize the segment results for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	248.2		$	88.8		$	22.6		$	(3.6)	$	—	$	356.0
Net written premiums	$	192.2		$	72.2		$	20.5		$	(2.6)	$	—	$	282.3
Net earned insurance and reinsurance premiums	$	243.5		$	114.3		$	17.2		$	(2.4)	$	—	$	372.6
Loss and allocated LAE(1)	(194.5)			(84.6)			(11.1)			(1.1)		—		(291.3)
Insurance and reinsurance acquisition expenses	(51.8)			(36.6)			(4.0)			(0.8)		9.6		(83.6)
Technical (loss) profit	(2.8)			(6.9)			2.1			(4.3)		9.6		(2.3)
Unallocated LAE(2)	(7.7)			(0.5)			(0.2)			(1.0)		(4.7)		(14.1)
Other underwriting expenses	(25.3)			(5.7)			(4.3)			(1.3)		(4.7)		(41.3)
Underwriting (loss) income	(35.8)			(13.1)			(2.4)			(6.6)		0.2		(57.7)
Service fee revenue(3)	—			26.3			—			0.9		(10.7)		16.5
Managing general underwriter unallocated LAE	—			(5.8)			—			—		5.8		—
Managing general underwriter other underwriting expenses	—			(4.7)			—			—		4.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(11.0)			—			(0.9)		—		(11.9)
Underwriting (loss) income, including net service fee income	(35.8)			(8.3)			(2.4)			(6.6)		—		(53.1)
Net investment income														1.7
Net realized investment gains														(3.8)
Net unrealized investment gains														31.2
Net foreign exchange (losses)														(21.3)
Other revenue(5)														(0.7)
General and administrative expenses(6)														(22.5)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(8.1)
Pre-tax (loss)														$	(80.5)
Underwriting Ratios(7)
Loss ratio	83.0		%	74.5		%	65.7		%	NM		NM		82.0		%
Acquisition expense ratio	21.3		%	32.0		%	23.3		%	NM		NM		22.4		%
Other underwriting expense ratio	10.4		%	5.0		%	25.0		%	NM		NM		11.1		%
Combined ratio(7)	114.7		%	111.5		%	114.0		%	NM		NM		115.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

13

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	256.3		$	137.4		$	17.9		$	2.1	$	—	$	413.7
Net written premiums	$	202.6		$	104.6		$	14.3		$	0.8	$	—	$	322.3
Net earned insurance and reinsurance premiums	$	249.5		$	115.1		$	9.1		$	0.5	$	—	$	374.2
Loss and allocated LAE(1)	(261.7)			(63.6)			(8.2)			(0.9)		—		(334.4)
Insurance and reinsurance acquisition expenses	(54.3)			(32.5)			(2.0)			(0.1)		13.8		(75.1)
Technical (loss) profit	(66.5)			19.0			(1.1)			(0.5)		13.8		(35.3)
Unallocated LAE(2)	(8.4)			(2.0)			(0.1)			(0.2)		(3.5)		(14.2)
Other underwriting expenses	(20.8)			(6.8)			(2.7)			(1.4)		(3.7)		(35.4)
Underwriting (loss) income	(95.7)			10.2			(3.9)			(2.1)		6.6		(84.9)
Service fee revenue(3)	—			31.0			—			—		(14.6)		16.4
Managing general underwriter unallocated LAE	—			(4.3)			—			—		4.3		—
Managing general underwriter other underwriting expenses	—			(3.7)			—			—		3.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(15.1)			—			(1.2)		—		(16.3)
Underwriting (loss) income, including net service fee income	(95.7)			18.1			(3.9)			(3.3)		—		(84.8)
Net investment income														22.8
Net realized investment gains														15.3
Net unrealized investment gains														53.9
Net foreign exchange gains														4.9
Other revenue(5)														(0.1)
General and administrative expenses(6)														(11.7)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(7.7)
Pre-tax (loss)														$	(11.3)
Underwriting Ratios(7)
Loss ratio	108.3		%	57.0		%	91.2		%	NM		NM		93.2		%
Acquisition expense ratio	21.8		%	28.2		%	22.0		%	NM		NM		20.1		%
Other underwriting expense ratio	8.3		%	5.9		%	29.7		%	NM		NM		9.5		%
Combined ratio(7)	138.4		%	91.1		%	142.9		%	NM		NM		122.8		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

14

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables summarize the segment results for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	927.0		$	434.6		$	68.9		$	65.7	$	—	$	1,496.2
Net written premiums	$	758.1		$	334.9		$	59.5		$	65.7	$	—	$	1,218.2
Net earned insurance and reinsurance premiums	$	719.4		$	345.4		$	45.2		$	67.1	$	—	$	1,177.1
Loss and allocated LAE(1)	(600.2)			(234.5)			(29.2)			(61.2)		—		(925.1)
Insurance and reinsurance acquisition expenses	(156.4)			(98.9)			(10.4)			(0.9)		30.2		(236.4)
Technical (loss) profit	(37.2)			12.0			5.6			5.0		30.2		15.6
Unallocated LAE(2)	(17.9)			(2.8)			(0.4)			(11.8)		(14.8)		(47.7)
Other underwriting expenses	(67.1)			(18.0)			(12.4)			(3.7)		(14.4)		(115.6)
Underwriting (loss) income	(122.2)			(8.8)			(7.2)			(10.5)		1.0		(147.7)
Service fee revenue(3)	—			85.3			—			0.9		(33.4)		52.8
Managing general underwriter unallocated LAE	—			(18.0)			—			—		18.0		—
Managing general underwriter other underwriting expenses	—			(14.4)			—			—		14.4		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(36.2)			—			(3.8)		—		(40.0)
Underwriting (loss) income, including net service fee income	(122.2)			7.9			(7.2)			(13.4)		—		(134.9)
Net investment income														30.0
Net realized investment gains														23.6
Net unrealized investment (losses)														(3.9)
Net foreign exchange (losses)														(18.9)
Other revenue(5)														(22.5)
General and administrative expenses(6)														(50.4)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.8)
Pre-tax (loss)														$	(212.6)
Underwriting Ratios(7)
Loss ratio	85.9		%	68.7		%	65.5		%	NM		NM		82.6		%
Acquisition expense ratio	21.7		%	28.6		%	23.0		%	NM		NM		20.1		%
Other underwriting expense ratio	9.3		%	5.2		%	27.4		%	NM		NM		9.8		%
Combined ratio(7)	116.9		%	102.5		%	115.9		%	NM		NM		112.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

15

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	1,008.4		$	459.5		$	50.5		$	4.7	$	—	$	1,523.1
Net written premiums	$	805.2		$	360.1		$	42.0		$	1.5	$	—	$	1,208.8
Net earned insurance and reinsurance premiums	$	705.7		$	330.0		$	19.9		$	1.2	$	—	$	1,056.8
Loss and allocated LAE(1)	(558.0)			(198.6)			(14.7)			(4.4)		—		(775.7)
Insurance and reinsurance acquisition expenses	(149.9)			(95.1)			(4.5)			(2.6)		36.7		(215.4)
Technical (loss) profit	(2.2)			36.3			0.7			(5.8)		36.7		65.7
Unallocated LAE(2)	(17.1)			(5.5)			(0.2)			(0.9)		(11.1)		(34.8)
Other underwriting expenses	(64.0)			(18.8)			(7.6)			(4.6)		(11.2)		(106.2)
Underwriting (loss) income	(83.3)			12.0			(7.1)			(11.3)		14.4		(75.3)
Service fee revenue(3)	—			97.6			—			—		(39.3)		58.3
Managing general underwriter unallocated LAE	—			(13.7)			—			—		13.7		—
Managing general underwriter other underwriting expenses	—			(11.2)			—			—		11.2		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(46.3)			—			(3.0)		—		(49.3)
Underwriting (loss) income, including net service fee income	(83.3)			38.4			(7.1)			(14.3)		—		(66.3)
Net investment income														67.3
Net realized investment gains														39.9
Net unrealized investment gains														143.4
Net foreign exchange gains														9.4
Other revenue(5)														(7.0)
General and administrative expenses(6)														(31.3)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.3)
Pre-tax income														$	120.3
Underwriting Ratios(7)
Loss ratio	81.5		%	61.8		%	74.9		%	NM		NM		76.7		%
Acquisition expense ratio	21.2		%	28.8		%	22.6		%	NM		NM		20.4		%
Other underwriting expense ratio	9.1		%	5.7		%	38.2		%	NM		NM		10.0		%
Combined ratio(7)	111.8		%	96.3		%	135.7		%	NM		NM		107.1		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

16

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	86.7	$	57.3	$	20.5	$	0.8	$	165.3
Europe	49.3		7.0		—		—		56.3
Canada, the Caribbean, Bermuda and Latin America	25.9		2.3		—		(3.6)		24.6
Asia and Other	30.3		5.6		—		0.2		36.1
Total net written premiums by client location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3
Total net written premiums by underwriting location:
United States	$	53.8	$	28.6	$	20.5	$	0.8	$	103.7
Europe	84.9		43.4		—		—		128.3
Canada, the Caribbean, Bermuda and Latin America	42.8		0.2		—		(3.6)		39.4
Asia and Other	10.7		—		—		0.2		10.9
Total net written premiums by underwriting location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	112.8	$	87.6	$	14.3	$	0.7	$	215.4
Europe	29.7		5.8		—		(0.1)		35.4
Canada, the Caribbean, Bermuda and Latin America	24.5		3.7		—		0.1		28.3
Asia and Other	35.6		7.5		—		0.1		43.2
Total net written premiums by client location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3
Total net written premiums by underwriting location:
United States	$	20.2	$	36.9	$	—	$	0.7	$	57.8
Europe	81.9		68.1		14.3		—		164.3
Canada, the Caribbean, Bermuda and Latin America	91.3		(0.6)		—		—		90.7
Asia and Other	9.2		0.2		—		0.1		9.5
Total net written premiums by underwriting location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3

17

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	297.9	$	288.7	$	59.5	$	68.4	$	714.5
Europe	264.8		19.4		—		0.4		284.6
Canada, the Caribbean, Bermuda and Latin America	74.2		10.1		—		(3.6)		80.7
Asia and Other	121.2		16.7		—		0.5		138.4
Total net written premiums by client location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2
Total net written premiums by underwriting location:
United States	$	162.5	$	185.7	$	59.5	$	68.4	$	476.1
Europe	376.3		149.4		—		0.4		526.1
Canada, the Caribbean, Bermuda and Latin America	174.6		(0.3)		—		(3.6)		170.7
Asia and Other	44.7		0.1		—		0.5		45.3
Total net written premiums by underwriting location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	382.1	$	301.2	$	42.0	$	1.0	$	726.3
Europe	207.7		18.9		—		0.1		226.7
Canada, the Caribbean, Bermuda and Latin America	70.2		10.7		—		0.1		81.0
Asia and Other	145.2		29.3		—		0.3		174.8
Total net written premiums by client location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8
Total net written premiums by underwriting location:
United States	$	57.8	$	136.0	$	—	$	1.0	$	194.8
Europe	368.0		190.1		42.0		0.2		600.3
Canada, the Caribbean, Bermuda and Latin America	334.4		33.4		—		—		367.8
Asia and Other	45.0		0.6		—		0.3		45.9
Total net written premiums by underwriting location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8

18

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 5. Reserves for unpaid losses and loss adjustment expenses

The following table summarizes the loss and LAE reserve activities of Sirius Group for the three and nine months ended September 30, 2020 and 2019:

	Three months ended September 30,				Nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross beginning balance	$	2,515.1	$	2,023.3	$	2,331.5	$	2,016.7
Less beginning reinsurance recoverable on unpaid losses	(442.2)		(357.4)		(410.3)		(350.2)
Net loss and LAE reserve balance	2,072.9		1,665.9		1,921.2		1,666.5
Losses and LAE incurred relating to:
Current year losses	305.5		342.2		967.5		723.6
Prior years losses	(0.1)		6.4		5.3		86.9
Total net incurred losses and LAE	305.4		348.6		972.8		810.5
Foreign currency translation adjustment to net loss and LAE reserves	20.8		(15.3)		12.2		(15.3)
Accretion of fair value adjustment to net loss and LAE reserves	0.1		—		0.1		0.1
Loss and LAE paid relating to:
Current year losses	81.6		97.7		149.2		254.8
Prior years losses	127.2		108.0		566.7		413.5
Total loss and LAE payments	208.8		205.7		715.9		668.3
Net ending balance	2,190.4		1,793.5		2,190.4		1,793.5
Plus ending reinsurance recoverable on unpaid losses	482.5		392.9		482.5		392.9
Gross ending balance	$	2,672.9	$	2,186.4	$	2,672.9	$	2,186.4

Loss and LAE development - Three Months Ended September 30, 2020

For the three months ended September 30, 2020, Sirius Group had a net favorable loss reserve development of $0.1 million. Favorable loss reserve development in U.S. Specialty ($0.8 million) and Runoff & Other ($0.4 million) were partially offset by unfavorable loss reserve development in Global Reinsurance ($1.3 million).

Loss and LAE development - Three Months Ended September 30, 2019

For the three months ended September 30, 2019, Sirius Group had net unfavorable loss reserve development of $6.4 million. Increases in loss reserve estimates were recorded in Global Reinsurance ($10.9 million) due to higher than expected activity in the Casualty Reinsurance book. These increases were partially offset by favorable loss reserve development in Global A&H ($5.8 million).

Loss and LAE development - Nine Months Ended September 30, 2020

For the nine months ended September 30, 2020, Sirius Group had net unfavorable loss reserve development of $5.3 million. Increases in loss reserve estimates for Global Reinsurance ($14.9 million) were partially offset by favorable loss reserve development in Global A&H ($7.6 million) and U.S. Specialty ($2.0 million). Within Global Reinsurance, unfavorable loss reserve development in Other Property ($21.6 million), Aviation & Space ($10.1 million) and Casualty Reinsurance ($9.2 million) was partially offset by favorable loss reserve development in Property Catastrophe Excess Reinsurance ($22.5 million). The reduction in Property Catastrophe Excess Reinsurance was due to reductions in reserve estimates for prior year catastrophe events, mainly Typhoons Faxai and Hagibis.

19

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Loss and LAE development - Nine Months Ended September 30, 2019

For the nine months ended September 30, 2019, Sirius Group had net unfavorable loss reserve development of $86.9 million. Increases in loss reserve estimates were recorded in Global Reinsurance ($82.7 million) and Runoff & Other ($5.4 million). The unfavorable loss reserve development in Global Reinsurance was primarily attributable to higher prior year catastrophe events, including Typhoon Jebi and Hurricanes Michael, Florence, and Irma.

Note 6. Third party reinsurance

In the normal course of business, Sirius Group seeks to protect its businesses from losses due to concentration of risk and losses arising from catastrophic events by reinsuring with third-party reinsurers. Sirius Group remains liable for risks reinsured in the event that the reinsurer does not honor its obligations under reinsurance contracts.

At September 30, 2020, Sirius Group had Reinsurance recoverable on paid losses of $70.4 million and Reinsurance recoverable on unpaid losses of $482.5 million. At December 31, 2019, Sirius Group had Reinsurance recoverable on paid losses of $73.9 million and Reinsurance recoverable on unpaid losses of $410.3 million. Because retrocessional reinsurance contracts do not relieve Sirius Group of its obligation to its insureds, the collectability of balances due from Sirius Group's reinsurers is important to its financial strength. Sirius Group monitors the financial strength and ratings of retrocessionaires on an ongoing basis. Uncollectible amounts historically have not been significant. (See Note 7.)

Note 7. Allowance for expected credit losses

Sirius Group is exposed to credit losses primarily through sales of its insurance and reinsurance products and services. The financial assets in scope of the current expected credit losses impairment model primarily include Sirius Group's premium receivables and reinsurance recoverables. Sirius Group pools the premium receivables and reinsurance recoverables by counterparty credit rating and applies a credit default rate that is determined based on the studies published by the rating agencies (e.g., A.M. Best, Standard & Poor's ("S&P")). In circumstances where ratings are unavailable, Sirius Group applies an internally developed default rate based on historical experience, reference data including research publications, and other relevant inputs.

To estimate the allowance for expected credit losses, Sirius Group considered the current and expected future economic and market conditions surrounding the COVID-19 pandemic. To the extent the current environment continues beyond our expectations or deteriorates further, we may experience further increases to our allowance for credit losses related to COVID-19.

As of September 30, 2020, Sirius Group's allowance for expected credit losses is as follows:

(in millions)	Gross Assets in Scope		Allowance for Expected Credit Losses
Premiums receivable & Funds held by ceding companies	$	1,033.1	$	10.6
Reinsurance recoverable on unpaid and paid loss	552.9		3.9
MGU Trade receivables(1)	17.2		0.4
Total as of September 30, 2020	$	1,603.2	$	14.9

(1) Included as part of Other assets on the Consolidated Balance Sheet

Sirius Group recorded no changes to the allowance for expected credit losses during three and nine months ended September 30, 2020.

Sirius Group monitors counterparty credit ratings and macroeconomic conditions, and considers the most current A.M. Best and S&P credit ratings to determine the allowance each quarter. Of the total gross assets in scope as of September 30, 2020, approximately 67% were balances with counterparties rated by either A.M. Best or S&P. Of the total rated, 63% were rated A- or better.

20

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 8. Investment securities

Sirius Group's invested assets consist of investment securities and other long-term investments held for general investment purposes. The portfolio of investment securities includes fixed maturity investments, short-term investments, equity securities, and other-long term investments which are all classified as trading securities. Realized and unrealized investment gains and losses on trading securities are reported in pre-tax revenues.

Net Investment Income

Sirius Group's net investment income is comprised primarily of interest income along with associated amortization of premium and accretion of discount on Sirius Group's fixed maturity investments, dividend income from its equity investments, and interest income from its short-term investments.

Net investment income for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	10.1	$	12.8	$	31.5	$	40.0
Short-term investments	0.6		4.1		5.2		12.0
Equity securities	0.8		2.7		5.5		12.5
Other long-term investments(1)(2)	(6.0)		5.2		(2.7)		12.3
Total investment income	5.5		24.8		39.5		76.8
Investment expenses	(3.8)		(2.0)		(9.5)		(9.5)
Net investment income	$	1.7	$	22.8	$	30.0	$	67.3

(1)Includes $(8.1) and $0.0 of interest on funds held for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $(7.5) and $0.6 of interest on funds held for the nine months ended September 30, 2020 and 2019, respectively.

Net Realized and Unrealized Investment Gains (Losses)

Net realized and unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross realized gains	$	41.3	$	22.1	$	140.7	$	63.1
Gross realized (losses)	(45.1)		(6.8)		(117.1)		(23.2)
Net realized (losses) gains on investments(1)(2)	(3.8)		15.3		23.6		39.9
Net unrealized gains (losses) on investments(3)(4)	31.2		53.9		(3.9)		143.4
Net realized and unrealized gains (losses) on investments	$	27.4	$	69.2	$	19.7	$	183.3

(1)Includes $(11.2) and $14.0 of realized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $5.4 and $34.5 of realized gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

(3)Includes $(16.7) and $33.9 of unrealized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(4)Includes $(29.8) and $51.7 of unrealized (losses) gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

21

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Net realized investment gains

Net realized investment gains for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(0.4)	$	7.5	$	17.3	$	22.4
Equity securities	1.0		1.7		(5.0)		(0.1)
Short-term investments	(6.2)		6.5		(2.4)		9.7
Derivative instruments	1.8		(0.7)		10.3		(1.5)
Other long-term investments	—		0.3		3.4		9.4
Net realized investment (losses) gains	$	(3.8)	$	15.3	$	23.6	$	39.9

Net unrealized investment gains (losses)

Net unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(1.0)	$	31.4	$	2.2	$	72.1
Equity securities	18.5		12.0		(33.7)		50.4
Short-term investments	(3.1)		4.6		(3.2)		6.4
Derivative instruments	(0.8)		0.9		1.4		0.2
Other long-term investments	17.6		5.0		29.4		14.3
Net unrealized investment gains (losses)	$	31.2	$	53.9	$	(3.9)	$	143.4

The following table summarizes the amount of total gains (losses) included in earnings attributable to unrealized investment gains (losses) for Level 3 investments for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	—	$	—	$	0.3	$	—
Other long-term investments	8.2		(0.3)		3.1		10.1
Total unrealized investment gains (losses) – Level 3 investments	$	8.2	$	(0.3)	$	3.4	$	10.1

22

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Investment Holdings

Fixed maturity investments

The cost or amortized cost, gross unrealized investment gains (losses), net foreign currency gains (losses), and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	471.4	$	10.0	$	(0.8)	$	1.3	$	481.9
Asset-backed securities	740.0		8.4		(12.4)		(4.4)		731.6
Residential mortgage-backed securities	393.8		22.2		(0.9)		1.4		416.5
U.S. government and government agency	119.2		0.8		—		(3.6)		116.4
Commercial mortgage-backed securities	120.8		3.1		(1.7)		—		122.2
Non-U.S. government and government agency	71.4		0.4		(0.1)		(0.6)		71.1
Preferred stocks	14.9		3.1		(0.1)		—		17.9
U.S. States, municipalities and political subdivision	1.2		0.1		—		—		1.3
Total fixed maturity investments	$	1,932.7	$	48.1	$	(16.0)	$	(5.9)	$	1,958.9

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	458.6	$	5.2	$	(1.2)	$	11.5	$	474.1
Asset-backed securities	489.4		1.4		(3.9)		(0.1)		486.8
Residential mortgage-backed securities	426.2		10.5		(1.4)		3.6		438.9
U.S. government and government agency	111.5		0.7		(0.4)		(1.3)		110.5
Commercial mortgage-backed securities	88.5		0.9		(0.6)		0.2		89.0
Non-U.S. government and government agency	63.7		—		(0.7)		—		63.0
Preferred stocks	17.0		—		—		—		17.0
U.S. States, municipalities and political subdivision	1.7		—		—		—		1.7
Total fixed maturity investments	$	1,656.6	$	18.7	$	(8.2)	$	13.9	$	1,681.0

The weighted average duration of Sirius Group's fixed income portfolio as of September 30, 2020 was approximately 1.1 years, including short-term investments, and approximately 1.6 years excluding short-term investments.

23

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The cost or amortized cost and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019 are presented below by contractual maturity. Actual maturities could differ from contractual maturities because borrowers may have the right to call or prepay certain obligations with or without call or prepayment penalties.

	September 30, 2020				December 31, 2019
(Millions)	Cost or amortized cost		Fair value		Cost or amortized cost		Fair value
Due in one year or less	$	203.2	$	212.2	$	85.0	$	88.4
Due after one year through five years	406.7		404.4		479.1		490.3
Due after five years through ten years	41.0		41.7		46.3		46.0
Due after ten years	12.3		12.4		25.1		24.6
Mortgage-backed and asset-backed securities	1,254.6		1,270.3		1,004.1		1,014.7
Preferred stocks	14.9		17.9		17.0		17.0
Total	$	1,932.7	$	1,958.9	$	1,656.6	$	1,681.0

The following table summarizes the ratings and fair value of fixed maturity investments held in Sirius Group's investment portfolio as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
AAA	$	807.8	$	559.8
AA	734.4		724.3
A	213.7		219.0
BBB	99.2		95.8
Other	103.8		82.1
Total fixed maturity investments(1)	$	1,958.9	$	1,681.0

(1)Credit ratings are assigned based on the following hierarchy: 1) Standard & Poor's ("S&P") and 2) Moody's Investors Service ("Moody's").

At September 30, 2020, the above totals included $43.8 million of sub-prime securities. Of this total, $21.5 million was rated AAA, $18.7 million rated AA, $3.5 million rated A and $0.1 million classified as Other. At December 31, 2019, the above totals included $43.3 million of sub-prime securities. Of this total, $21.7 million was rated AAA, $18.4 million rated AA, $3.1 million rated A and $0.1 million classified as Other.

Equity securities and Other long-term investments

The cost or amortized cost, gross unrealized investment gains and losses, net foreign currency gains, and fair values of Sirius Group's equity securities and other long-term investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	170.0	$	27.8	$	(39.7)	$	0.6	$	158.7
Other long-term investments	$	327.5	$	75.5	$	(24.4)	$	9.4	$	388.0

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	379.2	$	55.6	$	(37.3)	$	7.7	$	405.2
Other long-term investments	$	315.4	$	49.9	$	(29.3)	$	10.8	$	346.8

24

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Equity securities at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Fixed income mutual funds	$	1.8	$	175.3
Common stocks	170.1		228.1
Other equity securities(1)	(13.2)		1.8
Total Equity securities	$	158.7	$	405.2

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

Other long-term investments at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Hedge funds and private equity funds	$	301.1	$	269.0
Limited liability companies and private equity securities	86.9		77.8
Total other long-term investments	$	388.0	$	346.8

Hedge Funds and Private Equity Funds

Sirius Group holds investments in hedge funds and private equity funds, which are included in Other long-term investments. The fair value of these investments has been estimated using the net asset value of the funds. As of September 30, 2020, Sirius Group held investments in 10 hedge funds and 32 private equity funds. The largest investment in a single fund was $66.3 million as of September 30, 2020 and $51.6 million as of December 31, 2019.

The following table summarizes investments in hedge funds and private equity interests by investment objective and sector as of September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair value		Unfunded commitments		Fair value		Unfunded commitments
Hedge funds:
Long/short multi-sector	$	54.9	$	—	$	53.0	—
Distressed mortgage credit	66.3		—		51.6		—
Private credit	22.1		—		21.5		—
Multi-sector	5.8		—		—		—
Other	1.2		—		1.4		—
Total hedge funds	150.3		—		127.5		—
Private equity funds:
Energy infrastructure & services	56.6		30.7		53.6		34.6
Multi-sector	13.4		8.1		8.7		7.8
Healthcare	29.1		6.3		25.9		10.4
Life settlement	20.6		—		23.9		—
Manufacturing/Industrial	27.7		—		27.6		3.9
Private equity secondaries	0.6		0.8		0.6		0.8
Other	2.8		1.8		1.2		2.6
Total private equity funds	150.8		47.7		141.5		60.1
Total hedge and private equity funds included in Other long-term investments	$	301.1	$	47.7	$	269.0	$	60.1

25

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Redemption of investments in certain hedge funds is subject to restrictions including lock-up periods where no redemptions or withdrawals are allowed, restrictions on redemption frequency, and advance notice periods for redemptions. Amounts requested for redemptions remain subject to market fluctuations until the redemption effective date, which generally falls at the end of the defined redemption period.

The following summarizes the September 30, 2020 fair value of hedge funds subject to restrictions on redemption frequency and advance notice period requirements for investments in active hedge funds:

	Notice Period
Redemption Frequency (Millions)	1-29 days notice		30-59 days notice		60-89 days notice		90-119 days notice		120+ days notice		Total
Monthly	$	5.8	$	—	$	30.5	$	—	$	—	$	36.3
Quarterly	—		0.6		24.4		66.3		—		$	91.3
Semi-annual	—		—		0.3		—		—		$	0.3
Annual	—		—		—		0.3		22.1		$	22.4
Total	$	5.8	$	0.6	$	55.2	$	66.6	$	22.1	$	150.3

Certain of the hedge fund and private equity fund investments in which Sirius Group is invested are no longer active and are in the process of disposing of their underlying investments. Distributions from such funds are remitted to investors as the fund's underlying investments are liquidated. As of September 30, 2020, no distributions were outstanding from these investments.

Investments in private equity funds are generally subject to a "lock-up" period during which investors may not request a redemption. Distributions prior to the expected termination date of the fund may be limited to dividends or proceeds arising from the liquidation of the fund's underlying investments. In addition, certain private equity funds provide an option to extend the lock-up period at either the sole discretion of the fund manager or upon agreement between the fund and the investors.

As of September 30, 2020, investments in private equity funds were subject to lock-up periods as follows:

(Millions)	1 - 3 years		3 – 5 years		5 – 10 years		Total
Private Equity Funds – expected lock up period remaining	$	53.9	$	19.0	$	77.9	$	150.8

Investments Held on Deposit or as Collateral

As of September 30, 2020 and December 31, 2019 investments of $1,202.9 million and $1,309.5 million, respectively, were held in trusts required to be maintained in relation to various reinsurance agreements. Sirius Group's reinsurance operations are required to maintain deposits with certain insurance regulatory agencies in order to maintain their insurance licenses. The fair value of such deposits that are included within total investments totaled $1,217.9 million and $1,315.5 million as of September 30, 2020 and December 31, 2019, respectively.

As of September 30, 2020, Sirius Group held $0.1 million of collateral in the form of short-term investments associated with Interest Rate Cap agreements. (See Note 12.)

Unsettled investment purchases and sales

As of September 30, 2020 and December 31, 2019 Sirius Group reported $29.9 million and $2.3 million, respectively, in Accounts payable on unsettled investment purchases.

As of September 30, 2020 and December 31, 2019, Sirius Group reported $19.2 million and $6.7 million, respectively, in Accounts receivable on unsettled investment sales.

26

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 9. Fair value measurements

Fair value measurements are categorized into a hierarchy that distinguishes between inputs based on market data from independent sources ("observable inputs") and a reporting entity's internal assumptions based upon the best information available when external market data is limited or unavailable ("unobservable inputs"). Quoted prices in active markets for identical assets or liabilities have the highest priority ("Level 1"), followed by observable inputs other than quoted prices, including prices for similar but not identical assets or liabilities ("Level 2"), and unobservable inputs, including the reporting entity's estimates of the assumptions that market participants would use, having the lowest priority ("Level 3").

The availability of observable inputs can vary from financial instrument to financial instrument and is affected by a wide variety factors including, for example, the type of financial instrument, whether the financial instrument is new and not yet established in the marketplace, and other characteristics particular to the instrument. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires significantly more judgment.

Accordingly, the degree of judgment exercised by management in determining fair value is greatest for instruments categorized in Level 3. In periods of market dislocation, the observability of prices and inputs may be reduced for many instruments. This may lead the Company to change the selection of the valuation technique (for example, from market to cash flow approach) or to use multiple valuation techniques to estimate the fair value of a financial instrument. These circumstances could cause an instrument to be reclassified between levels within the fair value hierarchy. Investments valued using Level 1 inputs include fixed maturity investments, primarily investments in U.S. Treasuries Bills and Notes, equity securities, and short-term investments. Investments valued using Level 2 inputs are primarily comprised of fixed maturity investments, which have been disaggregated into classes, including U.S. government and government agency, corporate debt securities, mortgage-backed and asset-backed securities, non-U.S. government and government agency, U.S. state and municipalities and political subdivision and preferred stocks. Investments valued using Level 2 inputs also include certain exchange-traded funds that track U.S. stock indices such as the S&P 500 but are traded on foreign exchanges. Fair value estimates for investments that trade infrequently and have few or no observable market prices are classified as Level 3 measurements. Sirius Group determines when transfers between levels have occurred as of the beginning of the period.

Valuation techniques

Sirius Group uses outside pricing services to assist in determining fair values for its investments. For investments in active markets, Sirius Group uses the quoted market prices provided by outside pricing services to determine fair value. The outside pricing services Sirius Group uses have indicated that they will only provide prices where observable inputs are available. In circumstances where quoted market prices are unavailable or are not considered reasonable, Sirius Group estimates the fair value using industry standard pricing models and observable inputs such as benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers, prepayment speeds, reference data including research publications, and other relevant inputs. Given that many fixed maturity investments do not trade on a daily basis, the outside pricing services evaluate a wide range of fixed maturity investments by regularly drawing parallels from recent trades and quotes of comparable securities with similar features. The characteristics used to identify comparable fixed maturity investments vary by asset type and take into account market convention.

The valuation process above is generally applicable to all of Sirius Group's fixed maturity investments. The techniques and inputs specific to asset classes within Sirius Group's fixed maturity investments for Level 2 securities that use observable inputs are as follows:

U.S. government and government agency

U.S. government and government agency securities consist primarily of debt securities issued by the U.S. Treasury and mortgage pass-through agencies such as the Federal National Mortgage Association, the Federal Home Loan Mortgage Corporation and the Government National Mortgage Association. Fixed maturity investments included in U.S. government and government agency securities are primarily priced by pricing services. When evaluating these securities, the pricing services gather information from market sources and integrate other observations from markets and sector news. Evaluations are updated by obtaining broker-dealer quotes and other market information including actual trade volumes, when available. The fair value of each security is individually computed using analytical models that incorporate option-adjusted spreads and other daily interest rate data.

27

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Non-U.S. government and government agency

Non-U.S. government and government agency securities consist of debt securities issued by non-U.S. governments and their agencies along with supranational organizations (also known as sovereign debt securities). Securities held in these sectors are primarily priced by pricing services that employ proprietary discounted cash flow models to value the securities. Key quantitative inputs for these models are daily observed benchmark curves for treasury, swap, and high issuance credits. The pricing services then apply a credit spread for each security, which is developed by in-depth and real-time market analysis. For securities in which trade volume is low, the pricing services utilize data from more frequently traded securities with similar attributes. These models may also be supplemented by daily market and credit research for international markets.

Corporate debt securities

Corporate debt securities consist primarily of investment-grade debt of a wide variety of U.S. and non-U.S. corporate issuers and industries. The corporate fixed maturity investments are primarily priced by pricing services. When evaluating these securities, the pricing services gather information from market sources regarding the issuer of the security and obtain credit data, as well as other observations, from markets and sector news. Evaluations are updated by obtaining broker-dealer quotes and other market information including actual trade volumes, when available. The pricing services also consider the specific terms and conditions of the securities, including any specific features that may influence risk.

Mortgage-backed and asset-backed securities

The fair value of mortgage and asset-backed securities is primarily priced by pricing services using a pricing model that utilizes information from market sources and leveraging similar securities. Key inputs include benchmark yields, reported trades, underlying tranche cash flow data and collateral performance, plus new issue data, as well as broker-dealer quotes, issuer spreads, two-sided markets, benchmark securities, bids, offers, and reference data including issuer, vintage, loan type, collateral attributes, prepayment speeds, default rates, recovery rates, cash flow stress testing, credit quality ratings, and market research publications.

U.S. states, municipalities and political subdivisions

The U.S. states, municipalities and political subdivisions portfolio contains debt securities issued by U.S. domiciled state and municipal entities. These securities are generally priced by independent pricing services using the techniques described for U.S. government and government agency securities described above.

Preferred stocks

The fair value of preferred stocks is generally priced by independent pricing services using an evaluated pricing model that calculates the appropriate spread over a comparable security for each issue. Key inputs include exchange prices (underlying and common stock of the same issuer), benchmark yields, reported trades, broker-dealer quotes, issuer spreads, two-sided markets, benchmark securities, bids, offers, and reference data including sector, coupon, credit quality ratings, duration, credit enhancements, early redemption features, and market research publications.

Level 3 Investments

Level 3 valuations are generated from techniques that use assumptions not observable in the market. These unobservable assumptions reflect Sirius Group's assumptions about what market participants would use in valuing the investment. Generally, certain securities may start out as Level 3 when they are originally issued but, as observable inputs become available in the market, they may be reclassified to Level 2.

Sirius Group employs a number of procedures to assess the reasonableness of the fair value measurements for its other long-term investments, including obtaining and reviewing the audited annual financial statements of hedge funds and private equity funds and periodically discussing each fund's pricing with the fund manager. However, since the fund managers do not provide sufficient information to evaluate the pricing inputs and methods for each underlying investment, the inputs are considered to be unobservable.

28

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The fair values of Sirius Group's investments in private equity securities and private debt instruments have been classified as Level 3 measurements. They are carried at fair value and are initially valued based on transaction price. Their valuation is subsequently estimated based on available evidence such as a market transaction in similar instruments and other financial information for the issuer.

Investments measured using Net Asset Value

The fair value of Sirius Group's investments in hedge funds and private equity funds has been determined using net asset value ("NAV"). The hedge fund's administrator provides quarterly updates of fair value in the form of Sirius Group's proportional interest in the underlying fund's NAV, which is deemed to approximate fair value, generally with a three month delay in valuation. The fair value of investment in hedge funds is measured using the NAV practical expedient and therefore has been not categorized within the fair value hierarchy. The private equity funds provide quarterly or semi-annual partnership capital statements with a three or six month delay which are used as a basis for valuation. These private equity investments vary in investment strategies and are not actively traded in any open markets. Due to a lag in reporting, some of the fund managers, fund administrators, or both, are unable to provide final fund valuations as of the Company's reporting date. In these circumstances, Sirius Group estimates the return of the current period and uses all credible information available. This includes utilizing preliminary estimates reported by its fund managers and using other information that is available to Sirius Group with respect to the underlying investments, as necessary.

29

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Fair Value Measurements by Level

The following tables summarize Sirius Group's financial assets and liabilities measured at fair value as of September 30, 2020 and December 31, 2019 by level:

	September 30, 2020
(Millions)	Fair Value		Level 1 Inputs		Level 2 Inputs		Level 3 Inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	116.4	$	115.4	$	1.0	$	—
Corporate debt securities	481.9		—		481.9		—
Residential mortgage-backed securities	416.5		—		416.5		—
Asset-backed securities	731.6		—		731.6		—
Commercial mortgage-backed securities	122.2		—		122.2		—
Non-U.S. government and government agency	71.1		20.8		50.3		—
Preferred stocks	17.9		—		15.3		2.6
U.S. States, municipalities, and political subdivision	1.3		—		1.3		—
Total fixed maturity investments	1,958.9		136.2		1,820.1		2.6
Equity securities:
Fixed income mutual funds	1.8		1.8		—		—
Common stocks	170.1		170.1		—		—
Other equity securities(1)	(13.2)		(16.9)		3.7		—
Total equity securities	158.7		155.0		3.7		—
Short-term investments	1,132.6		1,068.4		64.2		—
Other long-term investments(2)	86.9		—		—		86.9
Total investments	$	3,337.1	$	1,359.6	$	1,888.0	$	89.5
Loan participation	28.5		—		—		28.5
Derivative instruments	7.7		6.6		—		1.1
Total assets measured at fair value	$	3,373.3	$	1,366.2	$	1,888.0	$	119.1
Liabilities measured at fair value
Contingent consideration liabilities	$	0.3	$	—	$	—	$	0.3
Derivative instruments	3.6		0.1		—		3.5
Total liabilities measured at fair value	$	3.9	$	0.1	$	—	$	3.8

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

(2)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

30

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

	December 31, 2019
(Millions)	Fair value		Level 1 inputs		Level 2 inputs		Level 3 inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	110.5	$	109.1	$	1.4	$	—
Corporate debt securities	474.1		—		474.1		—
Asset-backed securities	486.8		—		486.8		—
Residential mortgage-backed securities	438.9		—		438.9		—
Commercial mortgage-backed securities	89.0		—		89.0		—
Non-U.S. government and government agency	63.0		31.7		31.3		—
Preferred stocks	17.0		—		—		17.0
U.S. States, municipalities, and political subdivision	1.7		—		1.7		—
Total fixed maturity investments	1,681.0		140.8		1,523.2		17.0
Equity securities:
Fixed income mutual funds	175.3		175.3		—		—
Common stocks	228.1		228.1		—		—
Other equity securities	1.8		—		1.8		—
Total equity securities	405.2		403.4		1.8		—
Short-term investments	1,085.2		1,073.7		11.5		—
Other long-term investments(1)	77.8		—		—		77.8
Total investments	$	3,249.2	$	1,617.9	$	1,536.5	$	94.8
Loan participation	20.0		—		—		20.0
Derivative instruments	11.4		1.3		—		10.1
Total assets measured at fair value	$	3,280.6	$	1,619.2	$	1,536.5	$	124.9
Liabilities measured at fair value
Contingent consideration liabilities	$	28.2	$	—	$	—	$	28.2
Derivative instruments	9.5		0.2		—		9.3
Total liabilities measured at fair value	$	37.7	$	0.2	$	—	$	37.5

(1)Excludes fair value of $269.0 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

31

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Rollforward of Level 3 fair value measurements

The following tables present changes in Level 3 for financial instruments measured at fair value for the three months ended September 30, 2020 and September 30, 2019:

	For the three months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2020	$	2.6	$	78.2	$	27.3	$	1.5	$	(22.9)
Total realized and unrealized gains (losses)	—		8.2		—		(1.7)		(0.3)
Foreign currency gains through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		—		2.5		—		—
Sales/Settlements(2)	—		—		(1.3)		(2.2)		22.9
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $4.5 payment of contingent consideration for the 2017 purchase of Armada.

	For the three months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2019	$	—	$	88.0	$	—	$	(3.6)	$	(30.8)
Total realized and unrealized (losses)	—		(0.3)		—		(2.0)		(2.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.0)		—		—		—
Purchases	17.0		—		—		—		—
Sales/Settlements(2)	—		(6.0)		—		3.4		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

32

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables present changes in Level 3 for financial instruments measured at fair value for the nine months ended September 30, 2020 and September 30, 2019:

	For the nine months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2020	$	17.0	$	77.8	$	20.0	$	0.8	$	(28.2)
Total realized and unrealized gains (losses)	2.6		3.1		—		(20.7)		(0.5)
Foreign currency (losses) through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		5.5		9.9		—		—
Sales/Settlements(2)	(17.0)		—		(1.4)		17.5		28.4
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $10.0 payment of contingent consideration for the 2017 purchase of Armada.

	For the nine months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2019	$	5.4	$	63.6	$	—	$	(0.5)	$	(28.8)
Total realized and unrealized gains (losses)	—		10.6		—		(7.7)		(4.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.5)		—		—		—
Purchases	17.0		15.8		—		—		—
Sales/Settlements(2)	(5.4)		(7.8)		—		6.0		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

Fair value measurements – transfers between levels

There were no transfers between Level 3 and Level 2 measurements during the three and nine months ended September 30, 2020 and 2019, respectively.

33

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Significant Unobservable Inputs

The table below presents information about the significant unobservable inputs used for recurring fair value measurements for certain Level 3 instruments as of September 30, 2020 and December 31, 2019, and includes only those instruments for which information about the inputs is reasonably available to Sirius Group, such as data from independent third-party valuation service providers and from internal valuation models.

(Millions, except share prices)	September 30, 2020
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities (1)	Purchase price of recent transaction	$	32.5	Purchase price	40.63
Preferred stock (1)	Purchase price of recent transaction	$	27.9	Purchase price	7.74
Loan participation (1)	Purchase price of recent transaction	$	18.5	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private equity securities (1)	Multiple of GAAP book value	$	13.3	Book value multiple	Range - 0.73x-0.91x Median - 0.82x
Loan participation (1)	Purchase price of recent transaction	$	10.0	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private debt instrument (1)	Discounted cash flow	$	6.2	Discount yield	Range - 11.87% - 12.32% Median - 12.08%
Private equity securities (1)	Purchase price of recent transaction	$	4.7	Purchase price	7.74
Private convertible debt instrument (1)	Unit price of recent transaction	$	2.0	Purchase price	7.74
Preferred stock (1)	Purchase price of recent transaction	$	1.9	Purchase price	$	1.9
Preferred stock (1)	Purchase price of recent transaction	$	0.7	Purchase price	$	0.7
Equity warrants	Option pricing model	$	0.5	Strike price	$	0.2
Currency swaps (2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Currency forwards(2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Private equity securities (1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Contingent consideration	External valuation model	$	(0.3)	Discounted future payment	$	(0.3)
Weather derivatives (2)	Third party appraisal	$	(3.5)	Broker quote	$	(3.5)

(1)As of September 30, 2020, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

(Millions, except share prices)	December 31, 2019
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities(1)	Share price of recent transaction	$	32.5	Purchase share price	$	40.6
Loan participation(1)	Purchase price of recent transaction	$	20.0	Purchase price	20.0
Preferred stock(1)	Share price of recent transaction	$	17.5	Purchase price	$	7.74
Private equity securities(1)	Multiple of GAAP book value	$	14.2	Book value multiple	0.9
Preferred stock(1)	Purchase price of recent transaction	$	12.2	Purchase price	$	12.2
Private debt instrument(1)	Purchase price of recent transaction	$	7.2	Purchase price	$	9.0
Weather derivatives(2)	Third party appraisal	$	7.0	Broker quote	$	7.0
Private equity securities(1)	Purchase price of recent transaction	$	5.1	Purchase price	$	7.74
Preferred stock(1)	Purchase price of recent transaction	$	4.8	Purchase price	$	4.80
Currency forwards(2)	Third party appraisal	$	2.7	Broker quote	$	2.7
Private equity securities(1)	Purchase price of recent transaction	$	1.0	Purchase price	$	10.0
Equity warrants(2)	Option pricing model	$	0.4	Strike price	$	0.2
Private equity securities(1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Currency swaps(2)	Third party appraisal	$	(3.6)	Broker quote	$	(3.6)
Currency forwards(2)	Third party appraisal	$	(5.7)	Broker quote	$	(5.7)
Contingent consideration	External valuation model	$	(28.2)	Discounted future payments	$	(28.2)

(1)As of December 31, 2019, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

34

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Financial instruments disclosed, but not carried at fair value

Sirius Group uses various financial instruments in the normal course of its business. The carrying values of Cash, Accrued investment income, certain other assets, Accounts payable on unsettled investment purchases, certain other liabilities, and other financial instruments not included in the table below approximated their fair values at September 30, 2020 and December 31, 2019, due to their respective short maturities. As these financial instruments are not actively traded, their respective fair values are classified within Level 3. The following table includes financial instruments for which the carrying value differs from the estimated fair values at September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair Value(1)		Carrying Value		Fair Value(1)		Carrying Value
Liabilities, Mezzanine equity, and Non-controlling interest:
2017 SEK Subordinated Notes	$	298.8	$	301.3	$	294.5	$	291.2
2016 SIG Senior Notes	$	394.7	$	394.5	$	394.5	$	394.0
Series B preference shares	$	244.5	$	197.5	$	186.4	$	223.0

(1)Fair value estimated by internal pricing and considered a Level 3 measurement.

Note 10. Debt and standby letters of credit facilities

Sirius Group's debt outstanding as of September 30, 2020 and December 31, 2019 consisted of the following:

(Millions)	September 30, 2020		Effective Rate(1)		December 31, 2019		Effective Rate(1)
2017 SEK Subordinated Notes, at face value	$	305.0	4.3	%	$	295.0	4.0	%
Unamortized issuance costs	(3.7)				(3.8)
2017 SEK Subordinated Notes, carrying value	301.3				291.2
2016 SIG Senior Notes, at face value	400.0		4.7	%	400.0		4.7	%
Unamortized discount	(2.1)				(2.3)
Unamortized issuance costs	(3.4)				(3.7)
2016 SIG Senior Notes, carrying value	394.5				394.0
Total debt	$	695.8			$	685.2

(1) Effective rate considers the effect of the debt issuance costs.

2017 SEK Subordinated Notes

On September 22, 2017, Sirius Group issued floating rate callable subordinated notes denominated in Swedish kronor ("SEK") in the amount of SEK 2,750.0 million (or $346.1 million on date of issuance) at a 100% issue price ("2017 SEK Subordinated Notes"). The 2017 SEK Subordinated Notes were issued in an offering that was exempt from the registration requirements of the Securities Act of 1933 (the "Securities Act"). The 2017 SEK Subordinated Notes bear interest on their principal amount at a floating rate equal to the applicable Stockholm Interbank Offered Rate ("STIBOR") for the relevant interest period plus an applicable margin, payable quarterly in arrears on March 22, June 22, September 22, and December 22 in each year commencing on December 22, 2017, until maturity in September 2047.

35

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Beginning on September 22, 2022, the 2017 SEK Subordinated Notes may be redeemed, in whole or in part, at Sirius Group's option. In addition, within 90 days following the occurrence of a Specified Event (as defined below), the 2017 SEK Subordinated Notes may be redeemed, in whole but not in part, at Sirius Group's option. "Specified Event" means (a) an "Additional Amounts Event" in connection with a change in laws, rules or regulations as a result of which Sirius Group is obligated to pay additional amounts on the notes in respect of any withholding or deduction for taxes, (b) a "Tax Event" in connection with a change in laws, rules or regulations as a result of which interest on the notes is no longer fully deductible by Sirius Group for income tax purposes in the applicable jurisdiction (to the extent that such interest was so deductible as of the time of such Tax Event), (c) a "Rating Methodology Event" in connection with a change in, or clarification to, the rating methodology of Standard & Poor's or Fitch that results in a materially unfavorable capital treatment of the notes, or (d) a "Regulatory Event" in connection with a change in, or clarification to, applicable supervisory regulations that results in the notes no longer qualifying as Tier 2 Capital.

Sirius Group incurred $4.6 million in expenses related to the issuance of the 2017 SEK Subordinated Notes (including SEK 27.5 million, or $3.5 million, in underwriting fees), which have been deferred and are being recognized into interest expense over the life of the 2017 SEK Subordinated Notes. For the three months ended September 30, 2020 and 2019, Sirius Group recognized $(10.7) million and $15.9 million, respectively, of foreign currency exchange (losses) gains on the remeasurement of the 2017 SEK Subordinated Notes into USD from SEK. For the nine months ended September 30, 2020 and 2019, Sirius Group recognized $(9.9) million and $27.2 million, respectively, of foreign currency exchange (losses) gains on the remeasurement of the 2017 SEK Subordinated Notes into USD from SEK.

Taking into effect the amortization of all underwriting and issuance expenses, and applicable STIBOR, the 2017 SEK Subordinated Notes yielded an effective rate of approximately 4.3% and 4.1% annualized for the three months ended September 30, 2020 and 2019, respectively. The effective rate for the nine months ended September 30, 2020 and 2019 were 4.3% and 4.0% annualized, respectively. Sirius Group recorded $3.3 million and $3.0 million of interest expense, inclusive of amortization of issuance costs on the 2017 SEK Subordinated Notes for the three months ended September 30, 2020 and 2019, respectively. Sirius Group recorded $9.4 million and $8.9 million of interest expense, inclusive of amortization of issuance costs on the 2017 SEK Subordinated Notes for the nine months ended September 30, 2020 and 2019, respectively.

2016 SIG Senior Notes

On November 1, 2016, Sirius Group issued $400.0 million face value of senior unsecured notes ("2016 SIG Senior Notes") at an issue price of 99.209% for net proceeds of $392.4 million after taking into effect both deferrable and non-deferrable issuance costs. The 2016 SIG Senior Notes were issued in an offering that was exempt from the registration requirements of the Securities Act. The 2016 SIG Senior Notes bear an annual interest rate of 4.6%, payable semi-annually in arrears on May 1, and November 1, in each year commencing on May 1, 2017, until maturity in November 2026.

Sirius Group incurred $5.1 million in expenses related to the issuance of the 2016 SIG Senior Notes (including $3.4 million in underwriting fees), which have been deferred and are being recognized into interest expense over the life of the 2016 SIG Senior Notes.

Taking into effect the amortization of the original issue discount and all underwriting and issuance expenses, the 2016 SIG Senior Notes yield an effective rate of approximately 4.7% per annum. Sirius Group recorded $4.8 million, inclusive of amortization of issuance costs on the 2016 SIG Senior Notes, for both three month periods ended September 30, 2020 and 2019. Sirius Group recorded $14.4 million, inclusive of amortization of issuance costs on the 2016 SIG Senior Notes, for both nine month periods ended September 30, 2020 and 2019.

Standby Letter of Credit Facilities

On November 9, 2019, Sirius International Insurance Corporation ("Sirius International"), a wholly owned subsidiary of the Company, renewed two standby letter of credit facility agreements totaling $125 million to provide capital support for Lloyd's Syndicate 1945. The first letter of credit is a renewal of a $90 million facility with Nordea Bank Finland Abp, London Branch, which is issued on an unsecured basis. The second letter of credit is a $35 million facility with DNB Bank ASA, Sweden Branch, $25 million of which is issued on an unsecured basis. Each facility is renewable annually. The above referenced facilities are subject to various affirmative, negative and financial covenants that the Company considers to be customary for such borrowings, including certain minimum net worth and maximum debt to capitalization standards.

36

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Sirius International has other secured letter of credit and trust arrangements with various financial institutions to support its insurance operations. As of September 30, 2020 and December 31, 2019, these secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust of SEK 4.4 billion and SEK 3.4 billion, respectively, or $488.3 million and $363.3 million, respectively (based on the September 30, 2020 and December 31, 2019 SEK to USD exchange rates). As of September 30, 2020 and December 31, 2019, Sirius America Insurance Company's trust arrangements were collateralized by pledged assets and assets in trust of $47.9 million and $57.7 million, respectively. As of September 30, 2020 and December 31, 2019, Sirius Bermuda's letters of credit and trust arrangements were collateralized by pledged assets and assets in trust of $519.9 million and $784.0 million, respectively.

Revolving Credit Facility

In February 2018, Sirius Group, through its indirectly wholly-owned subsidiary Sirius International Group, Ltd. entered into a three-year, $300 million senior unsecured revolving credit facility (the "Facility"). The Facility provides access to loans for working capital and general corporate purposes, and letters of credit to support obligations under insurance and reinsurance agreements and retrocessional agreements. The Facility is subject to various affirmative, negative and financial covenants that Sirius Group considers to be customary for such borrowings, including certain minimum net worth, maximum debt to capitalization, financial strength rating standards, and change in control provisions. As of September 30, 2020, there were no outstanding borrowings under the Facility.

Debt and Standby Letter of Credit Facility Covenants

As of September 30, 2020, Sirius Group was in compliance with all of the covenants under the 2017 SEK Subordinated Notes, the 2016 SIG Senior Notes, the Nordea Bank Finland Abp, London Branch facility, and the DNB Bank ASA, Sweden Branch facility. In addition, as of September 30, 2020, Sirius Group was in compliance with all of the covenants under the Facility.

Interest

Total interest expense incurred by Sirius Group for its indebtedness for the three months ended September 30, 2020 and 2019 was $8.1 million and $7.7 million, respectively. Total interest expense incurred by Sirius Group for its indebtedness for the nine months ended September 30, 2020 and 2019 was $23.8 million and $23.3 million, respectively. Total interest paid by Sirius Group for its indebtedness for the three months ended September 30, 2020 and 2019 was $3.3 million and $2.8 million, respectively. Total interest paid by Sirius Group for its indebtedness for the nine months ended September 30, 2020 and 2019 was $18.5 million and $17.7 million, respectively.

Note 11. Income taxes

The Company and its Bermuda-domiciled subsidiaries are not subject to Bermuda income tax under current Bermuda law. In the event there is a change in the current law such that taxes are imposed, the Company and its Bermuda-domiciled subsidiaries would be exempt from such tax until March 31, 2035, pursuant to the Bermuda Exempted Undertakings Tax Protection Act of 1966. The Company has subsidiaries and branches that operate in various other jurisdictions around the world that are subject to tax in the jurisdictions in which they operate. The jurisdictions in which the Company's subsidiaries and branches are subject to tax are Australia, Belgium, Canada, Denmark, Germany, Gibraltar, Hong Kong (China), Ireland, Luxembourg, Malaysia, Shanghai (China), Singapore, Spain, Sweden, Switzerland, the United Kingdom, and the United States.

For the three month period ended September 30, 2020, Sirius Group reported an income tax expense (benefit) of $23.5 million on pre-tax income (loss) of $(80.5) million. The difference between the effective tax rate on income from continuing operations and the Swedish statutory tax rate of 21.4% (the rate at which the majority of Sirius Group's worldwide operations are taxed) is primarily attributable to unrealized investment gains in specific U.S. entities and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate. For the nine month period ended September 30, 2020, Sirius Group reported an income tax expense (benefit) of $19.9 million on pre-tax income (loss) of $(212.6) million. The difference between the effective tax rate for the nine months ended September 30, 2020 and the Swedish statutory rate of 21.4% was primarily attributable to valuation allowances recorded against certain deferred tax assets, unrealized investment gains in specific U.S. entities, and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate.

37

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

For the three month period ended September 30, 2019, Sirius Group reported an income tax (benefit) of $(3.7) million on pre-tax (loss) of $(11.3) million. The effective tax rate was higher than the Swedish statutory tax rate of 21.4% primarily because of income recognized in jurisdictions with higher rates than Sweden and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate. For the nine month period ended September 30, 2019, Sirius Group reported an income tax expense of $15.6 million on pre-tax income of $120.3 million. The effective tax rate for the nine months ended September 30, 2019 was lower than the Swedish statutory rate of 21.4% primarily because of income recognized in countries with lower rates than Sweden and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate.

For purposes of estimating the annual effective tax rate for the nine month periods ended September 30, 2020 and 2019, respectively, Sirius Group took into consideration all year-to-date income and expense items including the change in unrealized investment gains (losses) and realized investment gains (losses) and such items on a forecasted basis for the remainder of each year. Based on applicable GAAP guidance, jurisdictions with a projected loss for the full year where no tax benefit can be recognized are excluded from the estimation of the annual effective tax rate.

The Tax Cuts and Jobs Act ("TCJA") includes a new Base Erosion and Anti-Abuse Minimum Tax ("BEAT") provision, which is essentially a minimum tax that is potentially applicable to certain otherwise deductible payments made by U.S. entities to non-U.S. affiliates, including cross-border interest payments and reinsurance premiums. The statutory BEAT rate is 10% in 2019-2025, and then rises to 12.5% in 2026 and thereafter. The TCJA also includes provisions for Global Intangible Low-Taxed Income ("GILTI") under which taxes on foreign income are imposed on the excess of a deemed return on tangible assets of certain foreign subsidiaries. Consistent with accounting guidance, Sirius Group will treat BEAT as an in period tax charge when incurred in future periods for which no deferred taxes need to be provided and has made an accounting policy election to treat GILTI taxes in a similar manner. No provision for income taxes related to BEAT or GILTI was recorded as of September 30, 2020 and December 31, 2019.

Sirius Group has capital and liquidity in many of its subsidiaries, some of which may reflect undistributed earnings. If such capital or liquidity were to be paid or distributed to the Company or Sirius Group's subsidiaries, as dividends or otherwise, they may be subject to income or withholding taxes. Sirius Group generally intends to operate, and manage its capital and liquidity, in a tax-efficient manner. However, the applicable tax laws in relevant countries are still evolving, including in connection with guidance and proposals from the Organisation for Economic Cooperation and Development. Accordingly, such payments or earnings may be subject to income or withholding tax in jurisdictions where they are not currently taxed or at higher rates of tax than currently taxed, and the applicable tax authorities could attempt to apply income or withholding tax to past earnings or payments.

In April 2020, the European Court of Justice (the “ECJ”) published a decision disallowing the eligibility of an unrelated Gibraltar company for a European Union directive providing relief from withholding taxes on cross-border dividends. More generally, as a result of Brexit, it is projected that Gibraltar companies will cease to be eligible for European Union tax directives from January 1, 2021. The Company has a subsidiary organized in Gibraltar which has been a party to cross-border transactions with affiliates. The Company has assessed the tax consequences of these developments and concluded that they should not materially impact the Company’s provision for income taxes.

Deferred tax asset, net of valuation allowance

Sirius Group's net deferred tax liability, net of the valuation allowance as of September 30, 2020 is $55.1 million. Of the $55.1 million, $25.0 million relates to net deferred tax assets in U.S. subsidiaries, $141.3 million relates to net deferred tax assets in Luxembourg subsidiaries, $213.8 million relates to net deferred tax liabilities in Sweden subsidiaries, and $7.6 million relates to other net deferred tax liability.

Sirius Group records a valuation allowance against deferred tax assets if it becomes more likely than not that all or a portion of a deferred tax asset will not be realized. Changes in valuation allowances from period to period are included in income tax expense in the period of change. In determining whether or not a valuation allowance, or change therein, is warranted, Sirius Group considers factors such as prior earnings history, expected future earnings, carryback and carryforward periods and strategies that if executed would result in the realization of a deferred tax asset. It is possible that certain planning strategies or projected earnings in certain subsidiaries may not be feasible to utilize the entire deferred tax asset, which could result in material changes to Sirius Group's deferred tax assets and tax expense.

38

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Uncertain tax positions

Recognition of the benefit of a given tax position is based upon whether a company determines that it is more likely than not that a tax position will be sustained upon examination based upon the technical merits of the position. In evaluating the more likely than not recognition threshold, Sirius Group must presume that the tax position will be subject to examination by a taxing authority with full knowledge of all relevant information. If the recognition threshold is met, then the tax position is measured at the largest amount of benefit that is more than 50% likely of being realized upon ultimate settlement.

As of September 30, 2020, the total reserve for unrecognized tax benefits is $47.5 million. If Sirius Group determines in the future that its reserves for unrecognized tax benefits on permanent differences and interest and penalties are not needed, the reversal of $47.3 million of such reserves as of September 30, 2020 would be recorded as an income tax benefit and would impact the effective tax rate. If Sirius Group determines in the future that its reserves for unrecognized tax benefits on temporary differences are not needed, the reversal of $0.2 million of such reserves as of September 30, 2020 would not impact the effective tax rate due to deferred tax accounting but would accelerate the payment of cash to the taxing authority. Most of Sirius Group's reserves for unrecognized tax benefits on permanent differences relate to interest deductions denied by the Swedish Tax Authority ("STA"), as described further below.

The STA has denied deductions claimed by two of the Company's Swedish subsidiaries in certain tax years for interest paid on intra-group debt instruments. Sirius Group has challenged the STA's denial in court based on the technical merits. In October 2018, one of the Swedish subsidiaries received an adverse decision from Sweden's Administrative Court, which Sirius Group has appealed. Sirius Group has taken into account this and other relevant developments in applicable Swedish tax law and has established a reserve for this uncertain tax position. As of September 30, 2020, the total amount of such reserve was $46.6 million. In connection with this matter, Sirius Group has also taken into account the Stock Purchase Agreement ("SPA") by which Sirius Group was sold to CMIG International Holding Pte. Ltd ("CMIG International") in 2016 and has recorded an indemnification asset. Pursuant to the SPA, the seller agreed to indemnify the buyer and Sirius Group for, among other things, (1) any additional tax liability in excess of Sirius Group's accounting for uncertain tax positions for tax periods prior to the sale of Sirius Group to CMIG International, and (2) an impairment in Sirius Group's net deferred tax assets resulting from a final determination by a tax authority. CMIG International has informed Sirius Group of their view that CMIG International, rather than Sirius Group, should be entitled to all of the proceeds of such an indemnification claim, while Sirius Group is of the view that it should be entitled to the proceeds of such an indemnification claim to the extent of the book value of the relevant deferred tax assets, and therefore, Sirius Group continues to carry the related indemnification asset on the balance sheet. While Sirius Group intends to continue challenging the STA's denial based on the technical merits (including appealing the adverse court decision received in October 2018), the ultimate resolution of these tax disputes is uncertain and no assurance can be given that there will be no material changes to Sirius Group's operating results or balance sheet in connection with these uncertain tax positions or the related indemnification.

With few exceptions, Sirius Group is no longer subject to U.S. federal, state or non-U.S. income tax examinations by tax authorities for years before 2015.

Note 12. Derivatives

Interest Rate Cap

Sirius Group entered into an interest rate swap ("Interest Rate Cap") with two financial institutions where it paid an upfront premium and in return receives a series of quarterly payments based on the 3-month London Interbank Offered Rate at the time of payment. The Interest Rate Cap does not qualify for hedge accounting. Changes in fair value are recognized as unrealized gains or losses and are presented within Other revenue. The fair value of the interest rate cap has been estimated using a single broker quote and, accordingly, has been classified as a Level 3 measurement as of September 30, 2020 and December 31, 2019. Collateral held is recorded within short-term investments with an equal amount recognized as a liability to return collateral. Sirius Group's liability to return that collateral is based on the amounts provided by the counterparties and investment earnings thereon. As of September 30, 2020 and December 31, 2019, Sirius Group held collateral balances of $0.1 million and $0.2 million, respectively

39

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Foreign Currency Risk Derivatives

Sirius Group executes foreign currency forwards, call options, swaps, and futures to manage foreign currency exposure. The foreign currency risk derivatives are not designated or accounted for under hedge accounting. Changes in fair value are recognized as unrealized gains or losses and are presented within Net foreign exchange gains. The fair value of the swaps and forwards are estimated using a single broker quote and accordingly, are classified as a Level 3 measurement. The fair value of the futures is widely available and have quoted prices in active markets and accordingly, were classified as a Level 1 measurement. Sirius Group did not provide or hold any collateral associated with the foreign currency risk derivatives.

Weather Derivatives

Sirius Group holds assets and assumes liabilities related to weather and weather contingent risk management products. Weather and weather contingent derivative contracts are entered into with the objective of generating profits in normal climatic conditions. Accordingly, Sirius Group's weather and weather contingent derivatives are not designed to meet the criteria for hedge accounting under GAAP. Sirius Group receives payment of premium at the contract inception in exchange for bearing the risk of variations in a quantifiable weather index. Changes in fair value are recognized as unrealized gains or losses and are presented within Other revenue. The fair value of the weather derivatives was estimated using a broker quote. Because of the significance of the unobservable inputs used to estimate the fair value of Sirius Group's weather risk contracts, the fair value measurements of the contracts are deemed to be Level 3 measurements in the fair value hierarchy as of September 30, 2020 and December 31, 2019. Sirius Group does not provide or hold any collateral associated with the weather derivatives.

Equity Contracts

Sirius Group executes trades in equity futures contracts, call options, and put options to hedge against positions in Common equities. The equity contracts are not designated or accounted for under hedge accounting. Changes in fair value are presented within Net unrealized investment (losses) gains. The fair value of the equity contracts is widely available and have quoted prices in active markets and accordingly, were classified as a Level 1 measurement.

Equity Warrants

Sirius Group holds restricted equity warrants as part of its investment strategy. The equity warrants are not designated or accounted for under hedge accounting. Changes in fair value are presented within Net unrealized investment (losses) gains. The fair value of the equity warrants is estimated using a single broker quote and accordingly, classified as a Level 3 measurement. Sirius Group did not provide or hold any collateral associated with the equity warrants.

40

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following tables summarize information on the classification and amount of the fair value of derivatives not designated as hedging instruments within the Company's Consolidated Balance Sheets as at September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020						December 31, 2019
Derivatives not designated as hedging instruments	Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)		Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)
Interest rate cap	$	250.0	$	—	$	—	$	250.0	$	—	$	—
Foreign currency swaps	$	40.0	$	0.3	$	—	$	90.0	$	—	$	3.6
Foreign currency forwards	$	225.2	$	0.3	$	—	$	(30.0)	$	2.7	$	5.7
Weather derivatives	$	53.6	$	—	$	3.5	$	110.7	$	7.0	$	—
Equity futures contracts	$	(1.0)	$	—	$	—	$	34.5	$	—	$	—
Foreign currency futures contracts	$	22.3	$	—	$	—	$	—	$	—	$	—
Equity call options	$	34.6	$	2.5	$	—	$	—	$	—	$	—
Equity put options	$	77.3	$	1.9	$	0.1	$	31.0	$	1.3	$	0.2
Foreign currency call options	$	50.6	$	2.2	$	—	$	—	$	—	$	—
Equity warrants	$	0.5	$	0.5	$	—	$	0.4	$	0.4	$	—

(1)Asset derivatives are classified within Other assets within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

(2)Liability derivatives are classified within Other liabilities within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

The following table summarizes information on the classification and net impact on earnings, recognized in the Company's Consolidated Statements of (Loss) Income relating to derivatives during the three and nine months ended September 30, 2020 and 2019:

(Millions)		For the three months ended September 30,				For the nine months ended September 30,
Derivatives not designated as hedging instruments	Classification of gains (losses) recognized in earnings	2020		2019		2020		2019
Interest rate cap	Other revenues	$	—	$	—	$	—	$	(0.2)
Foreign currency swaps	Net foreign exchange (losses) gains	$	(0.9)	$	3.7	$	1.8	$	6.1
Foreign currency forwards	Net foreign exchange (losses) gains	$	(0.4)	$	(7.8)	$	(0.9)	$	(10.8)
Weather derivatives	Other revenues	$	(0.4)	$	1.9	$	(21.8)	$	(3.6)
Equity futures contracts	Net realized investment (losses) gains	$	(0.2)	$	0.1	$	2.4	$	(0.7)
Equity futures contracts	Net unrealized investment gains (losses)	$	(0.1)	$	(0.5)	$	0.4	$	(0.6)
Foreign currency futures contracts	Net foreign exchange (losses) gains	$	0.8	$	—	$	0.1	$	—
Equity put options	Net realized investment (losses) gains	$	1.9	$	(0.8)	$	7.8	$	(0.8)
Equity put options	Net unrealized investment gains (losses)	$	(0.6)	$	0.7	$	0.8	$	0.2
Foreign currency call options	Net foreign exchange (losses) gains	$	1.0	$	—	$	0.8	$	—
Equity warrants	Net unrealized investment gains (losses)	$	(0.1)	$	0.3	$	0.1	$	0.7

41

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 13. Share-based compensation

Sirius Group's compensation plans include grants for various types of share-based and non-share-based compensation awards to key employees and directors of Sirius Group. During the quarter ended September 30, 2020, all of Sirius Group's outstanding performance shares units ("PSUs") were cancelled and converted into cash-based restricted share units ("RSUs") at the most recent forecasted performance percentage. As of September 30, 2020, Sirius Group's share-based awards consisted of RSUs, restricted stock and options. Additionally, during the quarter ended September 30, 2020, the Company's Compensation Committee approved to offer active employees the opportunity to early settle the 2018 long term incentive award at the recent forecasted performance percentage in cash with the remaining balance of share units converted into replacement cash-based RSUs with extended vesting periods.

Sirius Group recognized $(3.3) million and $3.0 million of compensation expense under the share-based awards during the three months ended September 30, 2020 and 2019, respectively. Sirius Group recognized $0.7 million and $3.1 million of compensation expense under the share-based awards during the nine months ended September 30, 2020 and 2019, respectively. Sirius Group paid $1.9 million and $3.3 million to employees for share-based awards during both the three and the nine months ended September 30, 2020 and 2019, respectively.

The following tables present unrecognized compensation cost associated with unvested awards and weighted average period over which it is expected to be recognized:

(Millions)	September 30, 2020
	RSUs		Stock Options
Unrecognized compensation cost related to unvested awards	$	6.4	$	1.3
Weighted average recognition period (years)	1.3 years		1.5 years

As of September 30, 2019, there were $27.1 million of unrecognized share-based compensation costs, which are expected to be recognized over two to three years.

The following table summarizes outstanding and changes in share-settled awards for the three and nine months ended September 30, 2020:

	Number of Shares
Three months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,274,752	1,374,945
Granted	—	—
Vested	—	—
Forfeited	1,060	—
Unvested, end of period	1,273,692	1,374,945

	Number of Shares
Nine months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,353,852	1,374,945
Granted	—	—
Vested	—	—
Forfeited	80,160	—
Unvested, end of period	1,273,692	1,374,945

42

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

In the comparative periods of three and nine months ended September 30, 2019, the Company granted members of the Board of Directors 2,424 restricted shares and 37,039 restricted shares, respectively. For the three months ended September 30, 2019, Sirius Group granted employees 7,059 PSUs and 16,471 RSUs. For the nine months ended September 30, 2019, Sirius Group granted employees 408,370 PSUs, 1,428,185 RSUs, and 1,374,944 stock options. During the three months ended September 30, 2019, Sirius Group's employees forfeited 43,230 PSUs and 25,936 RSUs. During the nine months ended September 30, 2019, Sirius Group's employees forfeited 57,565 PSUs and 71,988 RSUs.

Cash-Settled Awards

During the quarter ended September 30, 2020, Sirius Group recognized an expense of $6.1 million related to newly issued RSUs. Additionally, during the quarter ended September 30, 2020, phantom performance shares of the existing long-term incentive compensation award that was issued in February 2020, were converted into cash-based phantom restricted shares. During the three and nine months ended September 30, 2020, Sirius Group recognized an expense of $1.1 million and $4.2 million, respectively, related to this award.

In addition, in November 2019, Sirius Group issued retention awards to certain key employees that vest and are paid in equal proportions on or prior to March 15, 2020 and on or prior to March 15, 2021, subject to continued employment on the applicable vesting date. In total, the awards issued under this retention program were $13.8 million, of which, $6.9 million was paid on March 15, 2020. During the three and nine months ended September 30, 2020, Sirius Group recognized an expense of $1.6 million and $9.2 million, respectively, in General and administrative expenses.

Note 14. Common shareholder's equity, mezzanine equity, and non-controlling interests

Common shareholder's equity

The authorized share capital of the Company consists of 500,000,000 Common shares, $0.01 par value per share, and 100,000,000 Preference shares, $0.01 par value per share.

The following table presents changes in the Company's issued and outstanding Common shares for the three and nine months ended September 30, 2020 and 2019, respectively:

	Three months ended September 30,		Nine months ended September 30,
	2020	2019	2020	2019
Common shares:
Shares issued and outstanding, beginning of period	115,299,341	115,296,918	115,299,341	115,151,251
Issuance of shares to directors and employees	—	2,424	—	148,091
Shares issued and outstanding, end of period	115,299,341	115,299,342	115,299,341	115,299,342

Dividends

The Company did not pay dividends to common shareholders during the three and nine months ended September 30, 2020 and 2019.

Mezzanine equity

Series B Preference Shares

Sirius Group has issued 11,901,670 of the 15,000,000 designated Series B preference shares, with a par value of $0.01 per share.

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Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The Series B preference shares rank senior to common shares with respect to dividend rights, rights of liquidation, winding-up, or dissolution of the Company and junior to all of the Company's existing and future policyholder obligations and debt obligations. Without the consent of the holders of the Series B preference shares, the Company may not issue any class or series of shares that rank senior or pari passu with the Series B preference shares as to the payment of dividends or as to distribution of assets upon any voluntary or involuntary liquidation, winding-up or dissolution of the Company, if the aggregate gross proceeds from the issuance of all such senior or pari passu shares equals or exceeds $100 million.

The Company adjusts the carrying value of the Series B preference shares to equal the redemption value at the end of each reporting period. At September 30, 2020 and December 31, 2019, the balance of the Series B preference shares was $197.5 million and $223.0 million, respectively.

Non-controlling interests

Non-controlling interests consist of the ownership interests of non-controlling shareholders in consolidated entities and are presented separately on the balance sheet. At September 30, 2020 and December 31, 2019, Sirius Group's balance sheet included $1.8 million and $2.4 million, respectively, in non-controlling interests.

The following tables show the change in non-controlling interest for the three and nine months ended September 30, 2020 and 2019:

(Millions)	For the three months ended September 30, 2020		For the three months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.5	$	3.0
Net income attributable to non-controlling interests	0.2		0.4
Dividends paid	(1.0)		—
Other, net	0.1		—
Non-controlling interests, end of the period	$	1.8	$	3.4

(Millions)	For the nine months ended September 30, 2020		For the nine months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.4	$	1.7
Net income attributable to non-controlling interests	0.2		1.6
Dividends paid	(1.0)		—
Other, net	0.2		0.1
Non-controlling interests, end of the period	$	1.8	$	3.4

Alstead Re

As of September 30, 2020 and December 31, 2019, Sirius Group recorded non-controlling interest of $1.8 million and $2.3 million, respectively, in Alstead Re Insurance Company ("Alstead Re"). (See Note 17.)

Note 15. Earnings per share

Basic earnings per share is computed by dividing net income available to Sirius Group common shareholders by the weighted-average number of common shares outstanding during the period. Diluted earnings per share is computed by dividing net income (loss) available to Sirius Group common shareholders on a diluted basis by the weighted-average number of common shares outstanding adjusted to give effect to potentially dilutive securities.

The Series B preference shares qualify as participating securities, which requires the application of the two-class method to compute both basic and diluted earnings per share. The two-class method is an earnings allocation formula that treats participating securities as having rights to earnings that would otherwise have been available to common shareholders. The Series B preference shares have no obligation to absorb losses of the Company in periods of net loss.

44

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following table sets forth the computation of basic and diluted earnings per common share for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions, except share and per share information)	2020		2019		2020		2019
Basic earnings per share
Numerator:
Net income	$	(104.0)	$	(7.6)	$	(232.5)	$	104.7
Less: Income attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
Less: Change in carrying value of Series B preference shares	8.7		5.3		25.5		(3.9)
Net income available for dividends out of undistributed earnings	$	(95.5)	$	(2.7)	$	(207.2)	$	99.2
Less: Earnings attributable to Series B preference shares	—		—		—		(9.3)
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Basic earnings per share	$	(0.83)	$	(0.02)	$	(1.80)	$	0.78
Diluted earnings per share
Numerator:
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Add: Change in carrying value of Series B preference shares	—		(5.3)		(25.5)		—
Net income available to Sirius Group common shareholders on a diluted basis	$	(95.5)	$	(8.0)	$	(232.7)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Add: Series B preference shares	—		11,901,670		11,901,670		—
Add: Unvested performance share units and restricted share units	—		—		—		393,280
Weighted average shares outstanding for diluted earnings per share(1)	115,297,945		127,153,523		127,180,867		115,619,222
Diluted earnings per share	$	(0.83)	$	(0.06)	$	(1.83)	$	0.78

(1)For the three months ended September 30, 2020, there were a total of 26,057,275 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the three months ended September 30, 2019, there were 19,537,270 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2020, there were a total of 14,155,605 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2019, there were 31,045,660 potentially dilutive securities excluded from the calculation of Diluted earnings per share.

Note 16. Investments in unconsolidated entities

Sirius Group's investments in unconsolidated entities are included within Other long-term investments and consist of investments in common equity securities or similar instruments, which give Sirius Group the ability to exert significant influence over the investee's operating and financial policies ("equity method eligible unconsolidated entities"). Such investments may be accounted for under either the equity method or, alternatively, Sirius Group may elect to account for them under the fair value option.

45

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following table presents the components of Other long-term investments as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Equity method eligible unconsolidated entities, at fair value	$	166.8	$	151.9
Other unconsolidated investments, at fair value(1)	221.2		194.9
Total Other long-term investments(2)	$	388.0	$	346.8

(1)Includes Other long-term investments that are not equity method eligible.

(2)There were no investments accounted for using the equity method as of September 30, 2020 and December 31, 2019.

Equity method eligible unconsolidated entities, at fair value

Sirius Group has elected the fair value option to account for its equity method eligible investments accounted for as part of Other long-term investments for consistency of presentation with the rest of its investment portfolio. The following table presents Sirius Group's investments in equity method eligible unconsolidated entities as of September 30, 2020 and December 31, 2019:

	Ownership interest as of
Investee	September 30, 2020		December 31, 2019		Instrument Held
BE Reinsurance Limited	24.9	%	24.9	%	Common shares
BioVentures Investors (Offshore) IV LP	73.0	%	73.0	%	Units
Camden Partners Strategic Fund V (Cayman), LP	39.4	%	39.4	%	Units
Diamond LS I LP	15.6	%	16.0	%	Units
Gateway Fund LP	22.9	%	15.0	%	Units
Monarch	12.8	%	12.8	%	Units
New Energy Capital Infrastructure Credit Fund LP	29.8	%	30.5	%	Units
New Energy Capital Infrastructure Offshore Credit Fund LP	29.8	%	30.5	%	Units
Pie Preferred Stock(1)	30.1	%	30.1	%	Preferred shares
Pie Series B Preferred Stock(1)	23.4	%	22.4	%	Preferred shares
Quintana Energy Partners	21.8	%	21.8	%	Units
Tuckerman Capital V LP	48.3	%	48.3	%	Units
Tuckerman Capital V Co-Investment I LP	48.3	%	48.1	%	Units

(1)Sirius Group holds investments in several financing instruments of Pie Insurance Holdings, Inc.

Note 17. Variable interest entities

Sirius Group consolidates the results of operations and financial position of every voting interest entity ("VOE") in which it has a controlling financial interest and VIEs in which it is considered to be the primary beneficiary. The consolidation assessment, including the determination as to whether an entity qualifies as a VOE or VIE, depends on the facts and circumstances surrounding each entity.

46

Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Sirius Group has determined that Alstead Re is a VIE for which Sirius Group is the primary beneficiary and is required to consolidate it. The following table presents Alstead Re's assets and liabilities, as classified in the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Assets:
Fixed maturity investments	$	3.8	$	3.9
Short-term investments	0.5		0.5
Cash	0.1		0.1
Total investments	4.3		4.5
Insurance and reinsurance premiums receivable	(0.5)		(0.3)
Funds held by ceding companies	2.3		3.4
Deferred acquisition costs	—		0.3
Other assets	—		—
Total assets	$	6.2	$	7.9
Liabilities
Loss and loss adjustment expense reserves	$	0.3	$	0.5
Unearned insurance and reinsurance premiums	—		0.6
Other liabilities	0.1		0.1
Total liabilities	$	0.4	$	1.2

Sirius Group is a passive investor in certain third-party-managed hedge and private equity funds, some of which are VIEs. Sirius Group is not involved in the design or establishment of these VIEs, nor does it actively participate in the management of the VIEs. The exposure to loss from these investments is limited to the carrying value of the investments at the balance sheet date.

Sirius Group calculates maximum exposure to loss to be (i) the amount invested in the debt or equity of the VIE, (ii) the notional amount of VIE assets or liabilities where Sirius Group has also provided credit protection to the VIE with the VIE as the referenced obligation, and (iii) other commitments and guarantees to the VIE. Sirius Group does not have any VIEs that it sponsors nor any VIEs where it has recourse to it or has provided a guarantee to the VIE interest holders.

The following table presents total assets of unconsolidated VIEs in which Sirius Group holds a variable interest, as well as the maximum exposure to loss associated with these VIEs:

			Maximum Exposure to Loss
(Millions)	Total VIE Assets		On-Balance Sheet		Off-Balance Sheet		Total
September 30, 2020
Other long-term investments(1)	$	254.8	$	117.1	$	7.4	$	124.5
Total at September 30, 2020	$	254.8	$	117.1	$	7.4	$	124.5
December 31, 2019
Other long-term investments(1)	$	257.8	$	102.6	$	16.3	$	118.9
Total at December 31, 2019	$	257.8	$	102.6	$	16.3	$	118.9

(1)Comprised primarily of hedge funds and private equity funds.

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Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 18. Transactions with related parties

(Re)insurance contracts

In the normal course of business, Sirius Group enters into insurance and reinsurance contracts with certain of its insurance and MGU affiliates, or their subsidiaries. During the three and nine months ended September 30, 2020, these contracts resulted in gross written premiums of $16.0 million and $84.1 million, respectively. During the three and nine months ended September 30, 2019, these contracts resulted in gross written premiums of $21.7 million and $70.7 million, respectively. As of September 30, 2020 and December 31, 2019, Sirius Group had total receivables due from affiliates of $22.0 million and $16.1 million, respectively. As of both September 30, 2020 and December 31, 2019, Sirius Group had total payables due to affiliates of $0.9 million.

Transaction Matters Letter Agreement

On August 6, 2020, CM Bermuda, the Company, TPRE and CMIG International entered into a Transaction Matters Letter Agreement (the “Transaction Matters Agreement”), pursuant to which, among other things and subject to the terms and conditions thereof, the Company has agreed to pay for and reimburse CMIG International and CM Bermuda for certain legal expenses incurred by CMIG International and CM Bermuda in connection with the Transactions and the related sales process or other discussions between CMIG International, CM Bermuda and the Company occurring on or after March 6, 2020, and TPRE has agreed to assume such remaining payment obligations of the Company following the closing of the Merger. TPRE has also agreed to pay for the fees and expenses payable by CMIG International and CM Bermuda to its financial advisor, Goldman Sachs (Asia) L.L.C., relating to the Transactions. Under the terms of the Transaction Matters Agreement, the Company is not permitted to terminate or threaten to terminate the Merger Agreement following a change by the TPRE board of directors of its recommendation to TPRE’s shareholders in favor of the TPRE Share Issuance without the prior written consent of CM Bermuda and CMIG International. During the quarter ended September 30, 2020, the Company paid $2.2 million for certain legal expenses incurred by CM Bermuda and CMIG International in connection with the Transaction Matters Agreement.

Series B preference shareholders expense reimbursement agreement

On March 27, 2020, the Company entered into an expense reimbursement agreement (the “Agreement”) with each of the holders of the Series B preference shares. Pursuant to the Agreement, the Company agreed to reimburse each of the holders of the Series B preference shares for all reasonable and documented out-of-pocket expenses incurred by them in connection with pursuing a potential negotiated transaction (a “Potential Transaction”) involving the Company or one or more of its subsidiaries on or after January 8, 2020 up to $250,000 for each holder of Series B preference shares together with its affiliates and $1,000,000 in the aggregate with any reimbursement above such amounts requiring the written consent of the Company (but excluding any expenses incurred in connection with the evaluation or enforcement of any rights or obligations of the holders of the Series B preference shares or the Company relating to the preference shares in the Company held by such Series B preference shareholders). In addition, the Company agreed to reimburse the holders of the Series B preference shares for any and all reasonable and documented out-of-pocket attorneys’ fees or other fees payable to third party advisors up to $500,000 in the aggregate to the extent arising out of any litigation, dispute, arbitration or other proceeding commencing after the date of the Agreement that is not brought or commenced by a holder of the Series B preference shares and involves the Company, such Series B preference shareholder's investment in the Company or a Potential Transaction. As of the end of the third quarter 2020, no payments have been requested or made under the Agreement.

Other

Meyer "Sandy" Frucher is the Company's Chairman of the Board of Directors and was also Vice Chairman of Nasdaq, Inc. ("Nasdaq") until December 2019. On January 1, 2020, Mr. Frucher concluded his tenure as Vice Chairman of Nasdaq and assumed the role of Strategic Advisor to Nasdaq. The Company is traded on the Nasdaq Global Select Market and has business transactions that are related to its listing on the exchange under the normal course of business. (See Note 3.)

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Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

Note 19. Commitments and contingencies

Legal Proceedings

Sirius Group, and the insurance and reinsurance industry in general, are routinely subject to claims related litigation and arbitration in the normal course of business, as well as litigation and arbitration that do not arise from, or are directly related to, claims activity. Sirius Group's estimates of the costs of settling matters routinely encountered in claims activity are reflected in the reserves for unpaid loss and LAE. (See Note 5.)

Sirius Group considers the requirements of ASC 450, Contingencies ("ASC 450"), when evaluating its exposure to non-claims related litigation and arbitration. ASC 450 requires that accruals be established for litigation and arbitration if it is probable that a loss has been incurred and it can be reasonably estimated. ASC 450 also requires that litigation and arbitration be disclosed if it is probable that a loss has been incurred or if there is a reasonable possibility that a loss may have been incurred. Management has considered all pending and/or threatened non-claims related litigation and has not identified any matters triggering disclosure under ASC 450.

Leases

Sirius Group leases office space and equipment under various noncancelable operating lease agreements. The average life of the office leases is 7 years and the equipment leases is 3 years.

During the three and nine months ended September 30, 2020, Sirius Group recognized operating lease expense of $3.0 million and $9.0 million, respectively, including property taxes and routine maintenance expense as well as rental expenses related to short term leases. During the three and nine months ended September 30, 2019, Sirius Group recognized operating lease expense of $3.4 million and $9.3 million, respectively, including property taxes and routine maintenance expense as well as rental expenses related to short term leases.

As of September 30, 2020 and December 31, 2019, Sirius Group had $27.1 million and $27.4 million of operating lease right-of-use assets, respectively, included in Other assets. As of September 30, 2020 and December 31, 2019, Sirius Group had $29.0 million and $29.3 million of operating lease liability, respectively, included in Other liabilities.

The following table presents the lease balances within the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(millions)	Balance Sheet Classification	September 30, 2020	December 31, 2019
Operating lease right-of-use assets	Other assets	$27.1	$27.4
Current lease liabilities	Other liabilities	$9.2	$8.3
Non-current lease liabilities	Other liabilities	$19.8	$21.0

The following table presents weighted average remaining lease term and weighted average discount rate as of September 30, 2020:

Weighted average lease term (years) as at September 30, 2020
Leased offices	7 years
Leased equipment	3 years
Weighted average discount rate:
Leased offices	3.3	%
Leased equipment	3.3	%

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Sirius International Insurance Group, Ltd.

Notes to Consolidated Financial Statements

Unaudited

The following table presents future annual minimum rental payments required under non-cancellable leases and the present value discount to arrive at total lease liability as of September 30, 2020:

(Millions)	Future Payments
2020	$	2.4
2021	9.6
2022	9.5
2023	5.7
2024	2.3
2025 and after	1.2
Total future annual minimum rental payments as of September 30, 2020	30.7
Less: present value discount	(1.7)
Total lease liability as of September 30, 2020	$	29.0

As of September 30, 2020, the Company's future operating lease obligations that have not yet commenced are immaterial.

ITEM 2. MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

The following is management's discussion and analysis ("MD&A") of the Company's unaudited consolidated results of operations for the three and nine months ended September 30, 2020 and 2019 and the Company's consolidated financial condition, liquidity and capital resources as of September 30, 2020 and December 31, 2019. This discussion and analysis should be read in conjunction with our historical consolidated financial statements and the related notes appearing in our Annual Report on Form 10-K for the year ended December 31, 2019 (our "2019 Annual Report"), filed with the U.S. Securities and Exchange Commission ("SEC") on March 5, 2020, and the Company's Unaudited Consolidated Financial Statements and related notes included elsewhere in this Quarterly Report on Form 10-Q. The consolidated financial statements have been prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP").

The following MD&A includes forward-looking statements, which are subject to risks, uncertainties and other factors that could cause our actual results to differ materially from those expressed or implied by our forward-looking statements. See "Cautionary Note Regarding Forward-Looking Statements".

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INDEX TO MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

	Page
Overview	51
Executive Summary	55
Consolidated Results of Operations – Three Months and Nine Months Ended September 30, 2020 and 2019	57
Summary of Investment Results	60
Foreign Currency Translation	63
Results of Reportable Segments	65
Global Reinsurance	66
Global A&H	69
U.S. Specialty	71
Runoff & Other	73
Reinsurance Protection	74
Non-GAAP Financial Measures	76
Liquidity and Capital Resources	77
Off Balance Sheet Arrangements	83
Contractual Obligations and Commitments	83
Cash Flows	83
Summary of Critical Accounting Estimates	85

Overview

The Company is a Bermuda exempted company that provides multi-line insurance and reinsurance on a worldwide basis through its wholly owned subsidiaries. Sirius Group's key insurance and reinsurance subsidiaries include Sirius Bermuda Insurance Company Ltd. ("Sirius Bermuda"), Sirius International Insurance Corporation ("Sirius International"), Sirius America Insurance Company ("Sirius America"), Sirius International Corporate Member Limited, a Lloyd's of London ("Lloyd's") Corporate Member, and Sirius Global Solutions Holding Company ("Sirius Global Solutions"). In addition, Sirius International sponsors Lloyd's Syndicate 1945 ("Syndicate 1945") and Sirius International Corporate Member participates in the Lloyd's market, which in turn provides underwriting capacity to Syndicate 1945. In addition to the key insurance and reinsurance subsidiaries, we own two managing general underwriters ("MGUs"), International Medical Group, Inc. ("IMG") and ArmadaCorp Capital, LLC ("Armada").

Background and Recent Developments

Merger Agreement

On August 6, 2020, the Company announced that it had entered into an Agreement and Plan of Merger (the “Merger Agreement”), by and among the Company, Third Point Reinsurance Ltd., a Bermuda exempted company (“TPRE”), and Yoga Merger Sub Limited, a Bermuda exempted company and a wholly owned subsidiary of TPRE (“Merger Sub”). The Merger Agreement provides, among other things, that, upon the terms and subject to the conditions set forth in the Merger Agreement and a Statutory Merger Agreement to be executed by the Company, TPRE and Merger Sub (the “Statutory Merger Agreement”), Merger Sub will merge with and into the Company, with the Company surviving as a wholly owned subsidiary of TPRE (the “Merger”). The Merger Agreement, the Statutory Merger Agreement, and the consummation of the transactions contemplated by the Merger Agreement and the Statutory Merger Agreement, including the Merger (the “Transactions”), have been unanimously approved by the board of directors of each of the Company and TPRE. The consummation of the Transactions is expected to occur during the first quarter of 2021, subject to the satisfaction or waiver of applicable closing conditions.

Under the terms of the Merger Agreement, as of the effective time of the Merger, each issued and outstanding common share, par value $0.01 per share, of the Company (“Company Shares”) will be converted into the right to receive, at the election of the holder thereof, (i) $9.50 in cash, or (ii) (A) 0.743 of a common share, par value $0.10 per share, of TPRE (“TPRE Shares”) and

51

(B) one contractual contingent value right (each, a “CVR”), which will represent the right to receive a contingent cash payment, and which, taken together with the fraction of the TPRE Share received, guarantee that on the second anniversary of the closing date of the Merger, the electing shareholder will have received equity and cash with a value of at least $13.73 per share (the “Share & CVR Election”), or (iii) (A) $0.905 in cash, (B) a number of TPRE Shares equal to the Mixed Election Common Shares Exchange Ratio (as such term is defined in the Merger Agreement), (C) a number of newly issued Series A preference shares of TPRE (“TPRE Preference Shares”) equal to the Mixed Election Preference Shares Exchange Ratio (as such term is defined in the Merger Agreement), (D) 0.190 of a warrant issued by TPRE and (E) $0.905 aggregate principal amount of a right (each, an “Upside Right”) issued by TPRE (the “Mixed Election”). Elections must be made no later than ten (10) Business Days (as defined in the Merger Agreement) prior to the closing of the Transactions. Pursuant to the Voting and Support Agreement dated August 6, 2020 among CM Bermuda Limited ("CM Bermuda"), CMIG International Holding Pte. Ltd. ("CMIG International"), the Company, and TPRE (the "Voting and Support Agreement"), CM Bermuda, a Bermuda exempted company and majority shareholder of the Company, whose parent company is CMIG International has agreed to make the Mixed Election. Holders of Company Shares who do not make an election will be deemed to have made the Share & CVR Election. No fractional TPRE Shares or TPRE Preference Shares will be issued in the Merger, and holders of Company Shares will receive cash in lieu of any fractional TPRE Shares or TPRE Preference Shares. Dissenting Company shareholders will be entitled to exercise appraisal rights under Bermuda law.

The consummation of the Merger is subject to the satisfaction or waiver of certain conditions, including, among others, (i) the affirmative vote in favor of the approval of the Merger Agreement, the Merger and the Statutory Merger Agreement by the holders of a majority of the voting power of the Company Shares and the Company’s Series B preference shares, voting together as a single class, that are present (in person or by proxy) at the Company shareholder meeting called for such purpose, (ii) the affirmative vote in favor of the approval of the issuance of TPRE Shares in the Merger as contemplated by the Merger Agreement by the holders of at least a majority of the voting power of TPRE Shares that are present (in person or by proxy) at the TPRE shareholder meeting called for such purpose, (iii) the expiration or termination of any applicable waiting period (together with any extensions thereof) under the Hart-Scott-Rodino Antitrust Improvements Act of 1976 and any other applicable antitrust laws, (iv) the receipt of certain approvals under applicable insurance laws, (v) the absence of any effective order issued by any governmental authority or court of competent jurisdiction or other legal restraint prohibiting or preventing the consummation of the Merger, (vi) in the case of each party’s obligation to effect the Merger, the absence of a material adverse effect with respect to the other party and its subsidiaries, taken as a whole, since the date of the Merger Agreement, (vii) in the case of each party’s obligation to effect the Merger, subject to certain materiality exceptions, the accuracy of the representations and warranties made by the other party, and compliance by the other party in all material respects with such party’s respective obligations under the Merger Agreement and (viii) other customary closing conditions.

Sirius Group incurred various legal, advisory, and other consulting costs associated with the proposed Merger of $10 million, which are included in the Company's financial condition or results of operations as of and for the three and nine months ended September 30, 2020. As part of the amount incurred, $2 million is in connection with the Transaction Matters Letter Agreement entered into by Sirius Group, TPRE, CM Bermuda and CMIG International on August 6, 2020 (the "Transaction Matters Agreement").

For a further discussion on Sirius Group’s risks related to the Merger, see "Risks Related to the Merger" included in Part II, Item 1A. “Risk Factors” of this Quarterly Report on Form 10-Q.

COVID-19

The novel coronavirus (COVID-19) pandemic has adversely affected our business and our results of operations. Because of the size and duration of this pandemic, all of the direct and indirect consequences of COVID-19 are not yet known and may not emerge for some time. The future impact of the pandemic on us is highly uncertain and cannot be predicted. For a further discussion on Sirius Group’s risks related to COVID-19, see “The novel coronavirus (COVID-19) pandemic has adversely affected our business. Epidemics, pandemics, and other public health threats, including the ongoing COVID-19 pandemic, could have a material adverse effect on Sirius Group’s business, including our results of operations, financial position and/or liquidity, in a manner and to a degree that cannot be predicted” included in Part II, Item 1A. “Risk Factors” of this Quarterly Report on Form 10-Q.

The safety and welfare of our employees is our highest priority during the COVID-19 pandemic. We implemented various business continuity and crisis management procedures to ensure all functions remained fully operational, which included regular management meetings both globally and locally as well as the monitoring of core business processes and outcomes. Prior to our decision to work remotely, we confirmed that all of our employees had access to our network, telecommunications

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equipment, and would remain fully operational. As a result of these actions, we have experienced no material disruptions in our business operations that would affect our clients.

During the third quarter, we reviewed our inforce (re)insurance portfolios to reevaluate our estimate of ultimate losses from the COVID-19 pandemic, and as a result of new information and more detailed modeling, we increased our estimates by $39 million, which included $31 million of losses from Global A&H primarily from contracts covering infectious disease related expenses. For the nine months ended September 30, 2020, we recorded $192 million of estimated ultimate losses in our underwriting results, which includes losses from Property, Accident & Health, Contingency, Trade Credit, and to a lesser extent Casualty lines of business. This best estimate of ultimate loss was based on our evaluation of the information readily available at this time, including an analysis of reported claims, an underwriting review of in-force contracts, industry estimates of ultimate losses, and other factors requiring considerable judgment. There may be additional future losses from COVID-19 which have not yet been reflected in Sirius Group’s estimates, if loss emergence varies from our initial expectations.

COVID-19 has had a negative impact on general economic activity which has, in turn, negatively impacted our premium volumes. The degree of the continued impact will depend on the extent and duration of the economic contraction. As a result of the anticipated impact of the pandemic on our earned premiums, we may experience an increase in our underwriting expense ratio. Sirius Group has experienced and may continue to experience lower gross written premiums for travel medical and trip cancellation insurance.

During the first quarter of 2020, Sirius Group experienced losses in its investment portfolio as a result of volatile markets, such as a decline in interest rates, a sharp decline in equity markets, and a widening of credit risk spreads for bonds. In addition, the disruption in the financial markets caused by COVID-19 contributed to net unrealized investment losses, primarily due to the impact of changes in fair value on our equity investments and, to a lesser extent, change in unrealized losses in our fixed-income investment portfolio.

Contingent Consideration

On September 24, 2020, Sirius Group paid $4 million to WE B CEJS (formerly known as Armada Enterprises LLC) as a contingent consideration payment for the three-year contingent earn-out mechanism from the acquisition of Armada and its subsidiaries (the "Armada Earnout") for performance related to the 2019 underwriting year. Previously, on April 17, 2020, Sirius Group paid $6 million to WE B CEJS as a contingent consideration payment for performance related to the 2017 and 2018 underwriting years. See Note 3 "Significant transactions" in Sirius Group's audited financial statements included in our 2019 Annual Report for further details and discussion with respect to the Armada Earnout.

On July 2, 2020, Sirius Group paid $18 million to IMG Acquisition Holdings, LLC ("IMGAH") for the contingent consideration payment for the 2019 calendar year, which represents the final contingent consideration payment. See Note 3 "Significant transactions" in Sirius Group's audited financial statements included in our 2019 Annual Report for further details and discussion with respect to the IMGAH contingent consideration.

Empire Insurance Company

On July 7, 2020, Sirius Group sold 100% of the common shares of Empire Insurance Company (“Empire”) to Physicians' Reciprocal Insurers. Sirius Group received $11 million of proceeds and recognized a $1 million gain on the sale of these assets.

Loss Portfolio Transfer

On January 23, 2020, Sirius Group entered into a loss portfolio transfer (the "LPT") with Pacific Re, Inc. Under the agreement, Sirius Group received $70 million in cash and assumed net undiscounted loss and loss adjustment expenses ("LAE") reserves with the same value. In addition, Sirius Group recognized Gross written premium and Loss and loss adjustment expenses for $70 million.

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Reportable Segments

On December 31, 2019, Sirius Group completed an internal reorganization to optimize the Company's operations, better serve its clients and make the Company more nimble and efficient. Beginning on January 1, 2020, Sirius Group's reportable segments consist of four reportable segments – Global Reinsurance, Global A&H, U.S. Specialty, and Runoff & Other.

•Global Reinsurance consists of Sirius Group's underwriting lines of business that offer Other Property, Property Catastrophe Excess Reinsurance, Agriculture Reinsurance, Aviation & Space, Marine & Energy, Trade Credit, Contingency, and Casualty Reinsurance;

•Global A&H consists of Sirius Group's global accident and health insurance and reinsurance underwriting business along with IMG and Armada, which provide supplemental healthcare and medical travel insurance products as well as related administration services;

•U.S. Specialty consists of Sirius Group's specialty insurance product offerings, which includes Environmental, Surety, and Workers’ Compensation. In April 2020, the Company decided to exit the Surety business due to competitive market conditions in that business line and the recent economic downturn which presented new risks and challenges for this line of business; and

•Runoff & Other consists of the results of Sirius Global Solutions, which specializes in the acquisition and management of runoff liabilities for insurance and reinsurance companies, both in the United States and internationally, as well as asbestos risks, environmental risks and other long-tailed liability exposures.

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Executive Summary

Three Months Ended September 30, 2020 and 2019

Sirius Group ended the third quarter of 2020 with a net (loss) attributable to common shareholders of $(96) million and basic earnings per common share of $(0.83) and diluted earnings per share of $(0.83). This compares to net (loss) attributable to common shareholders of $(3) million and basic earnings per common share of $(0.02) and diluted earnings per share of $(0.06) for the three months ended September 30, 2019. The higher net (loss) attributable to common shareholders was driven primarily by lower net realized and unrealized investment gains as a result of foreign exchange losses, COVID-19 losses ($39 million), and non-investment related net foreign exchange losses, partially offset by lower catastrophe losses. During the three months ended September 30, 2020, Sirius Group recorded catastrophe losses, net of reinsurance and reinstatement premiums, of $53 million compared to $109 million for the three months ended September 30, 2019. The three months ended September 30, 2020 results included an insignificant amount of net favorable prior year loss reserve development compared to $6 million of net unfavorable prior year loss reserve development for the three months ended September 30, 2019.

Sirius Group reported a comprehensive (loss) of $(67) million for the three months ended September 30, 2020 compared to comprehensive (loss) of $(50) million for the three months ended September 30, 2019. The higher comprehensive (loss) was driven primarily by a net (loss) of $(104) million, partially offset by foreign currency translation gains of $38 million recognized through other comprehensive income for the three months ended September 30, 2020 compared to $(42) million of foreign currency translation (losses) recognized through other comprehensive income and a net loss of $(8) million for the three months ended September 30, 2019. See "Foreign Currency Translation" below.

Sirius Group's combined ratio was 115% for the three months ended September 30, 2020 compared to 123% for the three months ended September 30, 2019. The improvement in the combined ratio was due to lower catastrophe losses, partially offset by COVID-19 losses, net of reinsurance and additional premiums due, of $39 million (11 points). The combined ratio included 14 points of catastrophe losses for the three months ended September 30, 2020 compared to 29 points for the three months ended September 30, 2019. Sirius Group's combined ratio for the three months ended September 30, 2020 was impacted by an insignificant amount of net favorable prior year loss reserve development compared to 2 points of net unfavorable prior year loss reserve development for the three months ended September 30, 2019.

Nine Months Ended September 30, 2020 and 2019

Sirius Group ended the first nine months of 2020 with a net (loss) attributable to common shareholders of $(207) million and basic earnings per common share of $(1.80) and diluted earnings per share of $(1.83). This compares to net income attributable to common shareholders of $99 million and basic and diluted earnings per common share of $0.78 for the nine months ended September 30, 2019. The decrease was driven primarily by $192 million from COVID-19 losses, net of reinsurance and additional premiums due, lower net unfavorable prior year loss reserve development, and catastrophe losses. The nine months ended September 30, 2020 results included $5 million of net unfavorable prior year loss reserve development compared to $87 million of net unfavorable prior year loss reserve development for the nine months ended September 30, 2019. During the nine months ended September 30, 2020, Sirius Group recorded catastrophe losses, net of reinsurance and reinstatement premiums, of $72 million compared to $119 million for the nine months ended September 30, 2019.

Sirius Group reported a comprehensive (loss) of $(202) million for the nine months ended September 30, 2020 compared to comprehensive income of $34 million for the nine months ended September 30, 2019. The decrease was driven primarily by a net (loss) of $(233) million and a foreign currency translation gain of $31 million recognized through other comprehensive income for the nine months ended September 30, 2020 compared to net income of $105 million, partially offset by a foreign currency translation (losses) of $(69) million recognized through other comprehensive income, for the nine months ended September 30, 2019. See "Foreign Currency Translation" below.

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Sirius Group's combined ratio was 113% for the nine months ended September 30, 2020 compared to 107% for the nine months ended September 30, 2019. The increase in the combined ratio from the prior period was driven primarily by $192 million of COVID-19 losses (16 points), partially offset by lower net unfavorable prior year loss reserve development and catastrophe losses. Sirius Group's combined ratio for the nine months ended September 30, 2020 was impacted by less than 1 point of net unfavorable prior year loss reserve development compared to 8 points of net unfavorable prior year loss reserve development for the nine months ended September 30, 2019. The combined ratio included 6 points of catastrophe losses for the nine months ended September 30, 2020 compared to 11 points for the nine months ended September 30, 2019.

Book Value Per Common Share

Book value per common share was $12.66 as of September 30, 2020 compared to book value per common share of $13.18 as of June 30, 2020, a decrease of 3.9% due to the comprehensive (loss) of $(67) million recognized for the three months ended September 30, 2020.

Book value per common share was $12.66 as of September 30, 2020 compared to book value per common share of $14.23 as of December 31, 2019, a decrease of 11.0% due to the comprehensive (loss) of $(202) million recognized for the nine months ended September 30, 2020.

Total common shareholders’ equity at the end of the third quarter of 2020 was $1,459 million compared to $1,520 million as of June 30, 2020 and $1,640 million as of December 31, 2019.

Return on Equity

Return on Equity ("ROE"), calculated by dividing Net (loss) income attributable to Sirius Group's common shareholders for the period by beginning common shareholders' equity, was (6.3)% for the three months ended September 30, 2020 compared to (0.2)% for the three months ended September 30, 2019 due to a higher net (loss) recognized for the three months ended September 30, 2020.

ROE was (12.6)% for the nine months ended September 30, 2020 compared to 5.8% for the nine months ended September 30, 2019 due to the net (loss) recognized for the nine months ended September 30, 2020.

Tangible Book Value Per Common Share

Tangible book value per common share, which is derived by subtracting Goodwill, Intangible assets, and Net deferred tax liability on intangible assets from Book value, was $7.89 as of September 30, 2020 compared to $8.39 as of June 30, 2020, a decrease of 6.0% due to the comprehensive (loss) of $(67) million recognized for the three months ended September 30, 2020.

Tangible book value per common share was $7.89 as of September 30, 2020 compared to $9.39 as of December 31, 2019, a decrease of 16.0% due to the comprehensive (loss) of $(202) million recognized for the nine months ended September 30, 2020.

See "Non-GAAP Financial Measures" for an explanation and calculation of Tangible book value and Tangible book value per common share.

Operating (loss) attributable to common shareholders

For the three months ended September 30, 2020, Operating (loss) attributable to common shareholders was $(101) million compared to $(65) million for the three months ended September 30, 2019 primarily due to lower net investment income, transaction related expenses, and lower net service fee income, partially offset by a lower net underwriting (loss).

For the nine months ended September 30, 2020, Operating (loss) attributable to common shareholders was $(218) million compared to $(66) million for the nine months ended September 30, 2019 primarily due to a higher net underwriting (loss), lower net investment income, a higher loss from the change in the fair value of weather derivatives, and transaction related expenses.

See "Non-GAAP Financial Measures" for an explanation and calculation of Operating (loss) attributable to common shareholders.

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Consolidated Results of Operations – Three and Nine Months Ended September 30, 2020 and 2019

(Expressed in millions of U.S. dollars, except ratios, share and per share information)

	Three months ended September 30,						Nine months ended September 30,
	2020			2019			2020			2019
Revenues
Gross written premiums	$	356.0		$	413.7		$	1,496.2		$	1,523.1
Net written premiums	$	282.3		$	322.3		$	1,218.2		$	1,208.8
Net earned insurance and reinsurance premiums	$	372.6		$	374.2		$	1,177.1		$	1,056.8
Net investment income	1.7			22.8			30.0			67.3
Net realized investment (losses) gains	(3.8)			15.3			23.6			39.9
Net unrealized investment gains (losses)	31.2			53.9			(3.9)			143.4
Net foreign exchange (losses) gains	(21.3)			4.9			(18.9)			9.4
Other revenue	15.8			16.3			30.3			51.3
Total revenues	396.2			487.4			1,238.2			1,368.1
Expenses
Loss and loss adjustment expenses	305.4			348.6			972.8			810.5
Insurance and reinsurance acquisition expenses	83.6			75.1			236.4			215.4
Other underwriting expenses	41.3			35.4			115.6			106.2
General and administrative expenses	34.4			28.0			90.4			80.6
Intangible asset amortization expenses	3.9			3.9			11.8			11.8
Interest expense on debt	8.1			7.7			23.8			23.3
Total expenses	476.7			498.7			1,450.8			1,247.8
Pre-tax (loss) income	(80.5)			(11.3)			(212.6)			120.3
Income tax (expense) benefit	(23.5)			3.7			(19.9)			(15.6)
Net (loss) income	(104.0)			(7.6)			(232.5)			104.7
(Income) attributable to non-controlling interests	(0.2)			(0.4)			(0.2)			(1.6)
(Loss) income attributable to Sirius Group	(104.2)			(8.0)			(232.7)			103.1
Change in carrying value of Series B preference shares	8.7			5.3			25.5			(3.9)
Net (loss) income attributable to Sirius Group's common shareholders	$	(95.5)		$	(2.7)		$	(207.2)		$	99.2
Comprehensive (loss) income
Net (loss) income	$	(104.0)		$	(7.6)		$	(232.5)		$	104.7
Other comprehensive income (loss)
Change in foreign currency translation, net of tax	37.5			(42.3)			31.1			(69.0)
Total other comprehensive income (loss)	37.5			(42.3)			31.1			(69.0)
Comprehensive (loss) income	(66.5)			(49.9)			(201.4)			35.7
Net (income) attributable to non-controlling interests	(0.2)			(0.4)			(0.2)			(1.6)
Comprehensive (loss) income attributable to Sirius Group	$	(66.7)		$	(50.3)		$	(201.6)		$	34.1
Ratios:
Loss ratio(1)	82.0		%	93.2		%	82.6		%	76.7		%
Acquisition expense ratio(2)	22.4		%	20.1		%	20.1		%	20.4		%
Other underwriting expense ratio(3)	11.1		%	9.5		%	9.8		%	10.0		%
Combined ratio(4)	115.5		%	122.8		%	112.5		%	107.1		%
Selected financial data:
Basic earnings per common share and common shares equivalent	$	(0.83)		$	(0.02)		$	(1.80)		$	0.78
Diluted earnings per common share and common shares equivalent	$	(0.83)		$	(0.06)		$	(1.83)		$	0.78
Basic weighted average number of common shares and common share equivalents outstanding	115,297,945			115,251,853			115,279,197			115,225,942
Diluted weighted average number of common shares and common share equivalents outstanding	115,297,945			127,153,523			127,180,867			115,619,222
Return on equity(5)	(6.3)		%	(0.2)		%	(12.6)		%	5.8		%
Operating (loss) attributable to common shareholders(6)	$	(100.8)		$	(65.4)		$	(218.2)		$	(65.9)

(1) The loss ratio is calculated by dividing loss and LAE expenses by net earned insurance and reinsurance premiums.

(2) The acquisition expense ratio is calculated by dividing insurance and reinsurance acquisition expenses by net earned insurance and reinsurance premiums.

(3) The other underwriting expense ratio is calculated by dividing other underwriting expenses by net earned insurance and reinsurance premiums.

(4) The combined ratio is calculated by combining the loss ratio, the acquisition expense ratio, and the other underwriting expense ratio.

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(5) Return on equity is calculated by dividing Net (loss) income attributable to Sirius Group's common shareholders for the period by beginning common shareholders' equity.

(6) Operating (loss) attributable to common shareholders is a non-GAAP financial measure. See "Non-GAAP Financial Measures" for an explanation and calculation of Operating (loss) attributable to common shareholders.

	As of September 30, 2020		As of June 30, 2020		As of December 31, 2019
Selected balance sheet data:
Book value per common share (1)	$	12.66	$	13.18	$	14.23
Tangible book value per common share (2)	$	7.89	$	8.39	$	9.39

(1) Book value per common share is calculated by dividing Total common shareholders' equity by the total number of Common shares outstanding.

(2) Tangible book value per common share is a non-GAAP financial measure. See "Non-GAAP Financial Measures" for an explanation and calculation of Tangible book value per common share.

Three and Nine Months Ended September 30, 2020 and 2019

Gross written premiums – Gross written premiums for the three months ended September 30, 2020 were $356 million, a decrease of $58 million or 14% compared to gross written premiums of $414 million for the three months ended September 30, 2019, with Global A&H down 35%, Global Reinsurance down 3%, and U.S. Specialty up 28%. Gross written premiums declined due to the impact from COVID-19 and client reaction to Sirius Group's ratings actions, partially offset by continued growth for business written through Pie Insurance Holdings, Inc. (“Pie Insurance”). See "Results of Reportable Segments" below.

Gross written premiums for the nine months ended September 30, 2020 were $1,496 million, a decrease of $27 million or 2% compared to gross written premiums of $1,523 million for the nine months ended September 30, 2019, with U.S. Specialty up 35%, Global Reinsurance down 8%, and Global A&H down 5%. Runoff & Other gross written premiums increased to $66 million for the nine months ended September 30, 2020 from $5 million for the nine months ended September 30, 2019 primarily due to the LPT. Gross written premiums declined due to the impact from COVID-19 and client reaction to Sirius Group's ratings actions, partially offset by continued growth for business written through Pie Insurance. See "Results of Reportable Segments" below.

Net written premiums – Net written premiums for the three months ended September 30, 2020 were $282 million, a decrease of $40 million or 12% compared to net written premiums of $322 million for the three months ended September 30, 2019, with Global A&H down 31%, Global Reinsurance down 5%, and U.S. Specialty up 50%. See "Results of Reportable Segments" below.

Net written premiums for the nine months ended September 30, 2020 were $1,218 million, an increase of $9 million or 1% compared to net written premiums of $1,209 million for the nine months ended September 30, 2019, with U.S. Specialty up 43%, Global A&H down 7%, and Global Reinsurance down 6%. Runoff & Other net written premiums increased to $66 million for the nine months ended September 30, 2020 from $2 million for the nine months ended September 30, 2019 primarily due to the LPT. Absent the effect of the LPT within the Runoff & Other segment, net written premiums decreased 5% compared to the prior period. See "Results of Reportable Segments" below.

Net earned insurance and reinsurance premiums – Net earned insurance and reinsurance premiums for the three months ended September 30, 2020 were $373 million, a decrease of $1 million or less than 1% compared to net earned insurance and reinsurance premiums of $374 million for the three months ended September 30, 2019, with Global Reinsurance down 2%, Global A&H down 1%, and U.S. Specialty up 89%. See "Results of Reportable Segments" below.

Net earned insurance and reinsurance premiums for the nine months ended September 30, 2020 were $1,177 million, an increase of $120 million or 11% compared to net earned insurance and reinsurance premiums of $1,057 million for the nine months ended September 30, 2019, with U.S. Specialty up 125%, Global A&H up 5%, and Global Reinsurance up 2%. Runoff & Other net earned insurance and reinsurance premiums increased to $67 million for the nine months ended September 30, 2020 from $1 million for the nine months ended September 30, 2019 primarily due to the LPT. See "Results of Reportable Segments" below.

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Net investment income, Net realized investment (losses) gains, Net unrealized investment gains (losses), and Net foreign exchange (losses) gains – Net investment income decreased to $2 million for the three months ended September 30, 2020 from $23 million for the three months ended September 30, 2019 primarily due to a reduction of previously earned funds held interest that was a result of underwriting results on a runoff contract, lower yields from short-term and fixed maturity investments, lower income from equity securities due to lower holdings, lower income from other long-term investments, and higher investment expenses. Sirius Group reported net realized investment (losses) of $(4) million for the three months ended September 30, 2020, which included $(11) million of net realized foreign currency (losses), compared to net realized investment gains of $15 million for the three months ended September 30, 2019, which included $14 million of net realized foreign currency gains. Net unrealized investment gains were $31 million for the three months ended September 30, 2020, which included $(17) million of net unrealized foreign currency (losses), compared to net unrealized investment gains of $54 million for the three months ended September 30, 2019, which included $34 million of net unrealized foreign currency gains. See "Summary of Investment Results" below. Additionally, Sirius Group recorded $(21) million of non-investment related foreign exchange (losses) for the three months ended September 30, 2020 compared to $5 million of non-investment related foreign exchange gains for the three months ended September 30, 2019. Included in the amount for the three months ended September 30, 2020 is $(11) million of unfavorable currency movement on the 2017 SEK Subordinated Notes (as defined herein) compared to $16 million of favorable currency movement for the three months ended September 30, 2019. See "Foreign Currency Translation" below.

Net investment income decreased to $30 million for the nine months ended September 30, 2020 from $67 million for the nine months ended September 30, 2019 primarily due to a reduction of previously earned funds held interest that was a result of underwriting results on a runoff contract, lower yields from short-term and fixed maturity investments, lower income from equity securities due to lower holdings, and lower income from other long-term investments. Sirius Group reported net realized investment gains of $24 million for the nine months ended September 30, 2020, which included $5 million of foreign currency gains, compared to net realized investments gains of $40 million for the nine months ended September 30, 2019, which included $35 million of foreign currency gains. Net unrealized investment (losses) were $(4) million for the nine months ended September 30, 2020, which included $(30) million of net unrealized foreign currency (losses), compared to net unrealized investment gains of $143 million for the nine months ended September 30, 2019, which included $52 million of net unrealized foreign currency gains. See "Summary of Investment Results" below. Additionally, Sirius Group recorded $(19) million of non-investment related foreign exchange (losses) for the nine months ended September 30, 2020 compared to $9 million of non-investment related foreign exchange gains for the nine months ended September 30, 2019. Included in the amount for the nine months ended September 30, 2020 is $(10) million of unfavorable currency movement on the 2017 SEK Subordinated Notes (as defined herein) compared to $27 million of favorable currency movement for the nine months ended September 30, 2019. See "Foreign Currency Translation" below.

Other revenue – Other revenue was $16 million for each of the three months ended September 30, 2020 and 2019.

Other revenue decreased to $30 million for the nine months ended September 30, 2020 from $51 million for the nine months ended September 30, 2019. The decrease in other revenue was primarily attributable to a $(22) million (loss) on the change in the fair value of weather derivatives compared to a $(4) million (loss) for the nine months ended September 30, 2019.

Loss and loss adjustment expenses – Loss and loss adjustment expenses decreased 13% to $305 million for the three months ended September 30, 2020 from $349 million for the three months ended September 30, 2019 primarily due to lower catastrophe losses and net favorable prior year loss reserve development, partially offset by COVID-19 losses. See "Results of Reportable Segments" below.

Loss and loss adjustment expenses increased 20% to $973 million for the nine months ended September 30, 2020 from $811 million for the nine months ended September 30, 2019 primarily due to COVID-19 losses and increased net earned insurance and reinsurance premiums, partially offset by lower net unfavorable prior year loss reserve development and catastrophe losses. In addition, Runoff & Other loss and loss adjustment expenses increased to $73 million for the nine months ended September 30, 2020 from $5 million for the nine months ended September 30, 2019 primarily due to the LPT. See "Results of Reportable Segments" below.

Insurance and reinsurance acquisition expenses – Insurance and reinsurance acquisition expenses increased 12% to $84 million for the three months ended September 30, 2020 from $75 million for the three months ended September 30, 2019 primarily due to an increase in net earned insurance and reinsurance premiums for U.S. Specialty for the three months ended September 30, 2020 as well as business mix. See "Results of Reportable Segments" below.

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Insurance and reinsurance acquisition expenses increased 10% to $236 million for the nine months ended September 30, 2020 from $215 million for the nine months ended September 30, 2019 primarily due to an increase in net earned insurance and reinsurance premiums for U.S. Specialty, Global Reinsurance, and Global A&H for the nine months ended September 30, 2020 as well as business mix. See "Results of Reportable Segments" below.

Other underwriting expenses – Other underwriting expenses increased 17% to $41 million for the three months ended September 30, 2020 from $35 million for the three months ended September 30, 2019 due to higher variable compensation expenses. See "Results of Reportable Segments" below.

Other underwriting expenses increased 9% to $116 million for the nine months ended September 30, 2020 from $106 million for the nine months ended September 30, 2019 due to higher variable compensation expenses. See "Results of Reportable Segments" below.

General and administrative expenses – General and administrative expenses increased 21% to $34 million for the three months ended September 30, 2020 from $28 million for the three months ended September 30, 2019 primarily due to various legal, advisory, and other consulting costs associated with the proposed Merger and expenses related to retention awards that were issued to key employees in November 2019, partially offset by lower expenses from the MGUs. See Note 13 "Share-based compensation" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q for further details and discussion of the retention awards.

General and administrative expenses increased 11% to $90 million for the nine months ended September 30, 2020 from $81 million for the nine months ended September 30, 2019 due to the same reasons for the three months ended September 30, 2020 increase.

Summary of Investment Results

Pre-Tax Return on Investments

Total return on investments includes investment income, net realized gains and losses, and the change in unrealized gains and losses generated by the investment portfolio including equity method eligible investments for which we have made a fair value election. Total return is calculated on a pre-tax basis and includes the impact of investment related foreign exchange gains or losses whether reflected in pre-tax income or other comprehensive income, unless otherwise noted. Returns are calculated on average investments for the period displayed and presented gross of separately managed account fees as well as internal expenses in order to produce a better comparison to benchmark returns that exclude an expense load.

Sirius Group maintains an equity portfolio that consists of equity securities and other long-term investments, including hedge funds, private equity funds, and direct investments in privately held common equity securities investments. From time to time, Sirius Group may also invest in exchange-traded funds ("ETFs") and mutual funds. For return purposes, investments in fixed-income ETFs and mutual funds are included in the fixed income results and excluded from equity portfolio results. Returns exclude the impact of funds held interest, third-party currency swaps, forwards, options, and /or futures.

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A summary of Sirius Group's total pre-tax net investment results and performance metrics for the three and nine months ended September 30, 2020 and 2019, respectively, follows:

	Three months ended September 30,				Nine months ended September 30,
(Millions)	2020		2019		2020		2019
Pre-tax investment results
Net investment income	$	1.7	$	22.8	$	30.0	$	67.3
Net realized and unrealized investment gains (1)	27.4		69.2		19.7		183.3
Change in foreign currency translation on investments recognized through other comprehensive income(2)	45.1		(67.8)		44.1		(109.6)
Net pre-tax investment gains	$	74.2	$	24.2	$	93.8	$	141.0

(1) Includes foreign exchange (losses) gains for the three months ended September 30, 2020 and 2019 of $(27.8) million and $47.9 million, respectively, and for the nine months ended September 30, 2020 and 2019 of $(24.4) million and $86.2 million, respectively.

(2) Excludes non-investment related foreign exchange (losses) gains for the three months ended September 30, 2020 and 2019 of $(21.3) million and $4.9 million, respectively, and for the nine months ended September 30, 2020 and 2019 of $(18.9) million and $9.4 million, respectively.

	Three months ended September 30,				Nine months ended September 30,
	2020		2019		2020		2019
Performance metrics
Total fixed income investment returns:
In U.S. dollars	1.1	%	0.4	%	2.0	%	2.8	%
In local currencies	0.6	%	0.8	%	1.7	%	3.4	%
Bloomberg Barclays U.S. Agg 1-3 Year Total Return Value Unhedged USD	0.2	%	0.7	%	2.8	%	3.4	%
OMX Stockholm OMRX Total Bond Index	0.3	%	0.6	%	1.3	%	2.6	%
Total equity securities and other long-term investments returns:
In U.S. dollars	7.8	%	2.4	%	5.2	%	11.7	%
In local currencies	7.3	%	2.8	%	5.0	%	11.5	%
S&P 500 Index (total return)	8.9	%	1.7	%	5.6	%	20.6	%
Total consolidated portfolio
In U.S. dollars	2.2	%	0.8	%	2.6	%	4.4	%
In local currencies	1.8	%	1.2	%	2.3	%	4.8	%

Three and nine months ended September 30, 2020 and 2019

Sirius Group’s pre-tax total gross return on invested assets was 2.2% for the three months ended September 30, 2020 compared to 0.8% for the three months ended September 30, 2019. The result for the three months ended September 30, 2020 included foreign currency gains on investments, which increased the total pre-tax return by 0.4%. The currency gains for the third quarter of 2020 were generated from our Swedish kronor (“SEK”), Euro (“EUR”), and Canadian dollar (“CAD”) holdings as these currencies strengthened against the U.S. dollar. The result for the three months ended September 30, 2019 included foreign currency losses on investments, which decreased the total pre-tax return by 0.4%. The currency losses for the third quarter of 2019 were generated mainly from our SEK, EUR and CAD holdings.

Sirius Group’s pre-tax total gross return on invested assets was 2.6% for the nine months ended September 30, 2020 compared to 4.4% for the nine months ended September 30, 2019. The result for the nine months ended September 30, 2020 was impacted by the ongoing concern of the COVID-19 pandemic and included foreign currency gains on investments, which increased the total pre-tax return by 0.3%. The currency gains for the nine months ended September 30, 2020 were generated mainly from our SEK and EUR holdings as these currencies strengthened against the U.S. dollar. For the nine months ended September 30, 2019, currency reduced the total pre-tax return by 0.4%.

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Net investment income was $2 million for the three months ended September 30, 2020 compared to $23 million for the three months ended September 30, 2019 primarily due to a reduction of previously earned funds held interest that was a result of underwriting results on a runoff contract, lower yields from short-term and fixed maturity investments, lower income from equity securities due to lower holdings, lower income from other long-term investments, and higher investment expenses. Net investment income was $30 million for the nine months ended September 30, 2020 compared to $67 million for the nine months ended September 30, 2019 primarily due to a reduction of previously earned funds held interest that was a result of underwriting results on a runoff contract, lower yields from short-term and fixed maturity investments, lower income from equity securities due to lower holdings, and lower income from other long-term investments.

Net realized and unrealized investment gains on investments, excluding foreign currency, were $55 million for the three months ended September 30, 2020 compared to $21 million for the three months ended September 30, 2019 driven by favorable market conditions. Net realized and unrealized investment gains on investments, excluding foreign currency, were $44 million for the nine months ended September 30, 2020 compared to $97 million for the nine months ended September 30, 2019. The decrease was driven by unrealized investment losses consistent with overall market performance for the first nine months of 2020.

Fixed income results (including short-term investments)

As of September 30, 2020 and December 31, 2019, the fixed income portfolio duration was approximately 1.0 years and 1.5 years, respectively. The average credit quality of the fixed income portfolio, including short-term investments, was AA+ and AA as of September 30, 2020 and December 31, 2019, respectively. As of September 30, 2020 and December 31, 2019, Sirius Group held $497 million and $341 million, respectively, of non-U.S. denominated fixed income securities.

The fixed income portfolio returned 1.1% on a U.S. dollar basis and 0.6% in local currencies for the three months ended September 30, 2020. Our U.S. portfolio returned 0.7% versus the Bloomberg Barclays U.S. Aggregate 1-3 Year (“BarcAgg1-3”) of 0.2%. Our non-U.S. portfolio returned 0.2% in original currencies compared to the OMX Stockholm OMRX Total Return Bond Index (“OMRX”) of 0.3%. For the three months ended September 30, 2020, the outperformance of our U.S. portfolio against the index was due to a lower share of U.S. government issued securities compared to the BarcAgg1-3. The underperformance of our non-U.S portfolio was primarily due to the EUR and CAD positions, which did not perform well against the index. The fixed income portfolio gained 0.4% on a U.S. dollar basis and 0.8% in local currencies for the three months ended September 30, 2019. For the three months ended September 30, 2019, our U.S. portfolio returned 0.9% versus the BarcAgg1-3 of 0.7% and our non-U.S. portfolio returned 0.1% in original currencies versus the OMRX of 0.6%.

The fixed income portfolio returned 2.0% on a U.S. dollar basis and 1.7% in local currencies for the nine months ended September 30, 2020. Our U.S. portfolio returned 1.9% versus the BarcAgg1-3 of 2.8%. Our non-U.S. portfolio returned 0.8% in original currencies compared to the OMRX of 1.3%. For the nine months ended September 30, 2020, a lower duration in a decreasing interest rate environment adversely impacted our return versus the indices. The fixed income portfolio gained 2.8% on a U.S. dollar basis and 3.4% in local currencies for the nine months ended September 30, 2019. For the nine months ended September 30, 2019, our U.S. portfolio returned 3.7% versus the BarcAgg1-3 of 3.4% and our non-U.S. portfolio returned 0.9% in original currencies versus the OMRX of 2.6%. The lower duration of our portfolio adversely impacted our return versus the indices due to the decreasing interest rate environment.

Equity securities and other long-term investments results

As of September 30, 2020, the equity and other long-term investments portfolio included $563 million of U.S. dollar and $80 million of non-U.S. dollar denominated securities. As of December 31, 2019, the equity and other long-term investments portfolio included $482 million of U.S. dollar and $187 million of non-U.S. dollar denominated securities.

For the three months ended September 30, 2020, the equity portfolio returned 7.8% on a U.S. dollar basis and 7.3% on a local currency basis. The S&P 500 returned 8.9% for the same period. Performance lagged the index primarily due to the market neutral strategy of a large portion of our equity and other long-term investments portfolio. For the three months ended September 30, 2019, the equity portfolio gained 2.4% on a U.S. dollar basis and gained 2.8% in local currencies. The S&P 500 gained 1.7% for the same period.

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For the nine months ended September 30, 2020, the equity portfolio returned 5.2% on a U.S. dollar basis and 5.0% on a local currency basis. The S&P 500 returned 5.6% for the same period. The portfolio yielded a slightly lower performance, while experiencing much less volatility, than the S&P 500 for the nine months ended September 30, 2020 due to the market neutral strategy of a large portion of our equity and other long-term investments portfolio. For the nine months ended September 30, 2019, the equity portfolio returned 11.7% on a U.S. dollar basis and 11.5% in original currencies versus the S&P 500 of 20.6%. Performance lagged the S&P 500 due to the market neutral strategy previously discussed.

Foreign Currency Translation

Impact of Foreign Currency Translation

The U.S. dollar is the functional currency for Sirius Group's businesses except for Sirius International, Syndicate 1945, several subsidiaries of IMG, and the Canadian reinsurance operations of Sirius America. Sirius Group also invests in securities denominated in foreign currencies. Assets and liabilities recorded in these foreign currencies are translated into U.S. dollars at exchange rates in effect at the balance sheet date, and revenues and expenses are converted using the average exchange rates for the period. Net foreign exchange gains and losses arising from the translation of functional currencies into U.S. dollars are reported in common shareholders' equity and in Accumulated other comprehensive (loss). As of September 30, 2020 and December 31, 2019, Sirius Group had net unrealized foreign currency translation (losses) of $(206) million and $(238) million, respectively, recorded in Accumulated other comprehensive (loss) on its Consolidated Balance Sheets.

Assets and liabilities relating to foreign operations are remeasured into the functional currency using current exchange rates; revenues and expenses are remeasured into the functional currency using the weighted average exchange rate for the period. The resulting exchange gains and losses are reported as a component of Net income (loss) in the period in which they arise within Net realized investment gains (losses), Net unrealized investment gains (losses), and Net foreign exchange gains (losses).

The following rates of exchange for the U.S. dollar have been used for translation of investments whose functional currency is not the U.S. dollar as of September 30, 2020 and December 31, 2019:

Currency	Closing Rate September 30, 2020	Closing Rate December 31, 2019
Swedish kronor	9.0163	9.3210
British pound	0.7778	0.7568
Euro	0.8550	0.8912
Canadian dollar	1.3379	1.3003

Sirius International holds a large portfolio of investments that are denominated in U.S. dollars, but its functional currency is the SEK. When Sirius International prepares its stand-alone GAAP financial statements, it remeasures its U.S. dollar-denominated investments to SEK and recognizes the related foreign currency remeasurement gains or losses through pre-tax income (loss). When Sirius Group consolidates Sirius International, it translates Sirius International's stand-alone GAAP financial statements to U.S. dollars and recognizes the related foreign currency translation gains or losses through other comprehensive income (loss). Since Sirius Group reports its financial statements in U.S. dollars, there is no net effect to book value per common share or to investment returns from foreign currency translation on its U.S. dollar-denominated investments at Sirius International. However, net realized and unrealized investment gains (losses), other revenues, net income (loss), earnings per share, and other comprehensive income (loss) can be significantly affected during periods of high volatility in the foreign exchange rate between the U.S. dollar and other currencies, especially the SEK.

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A summary of the impact of foreign currency translation on Sirius Group's consolidated financial results for the three and nine months ended September 30, 2020 and 2019 follows:

(Millions)	Three months ended September 30,				Nine months ended September 30,
	2020		2019		2020		2019
Net realized investment (losses) gains - foreign currency(1)	$	(11.1)	$	14.0	$	5.4	$	34.5
Net unrealized investment (losses) gains - foreign currency(2)	(16.7)		33.9		(29.8)		51.7
Net realized and unrealized investment (losses) gains - foreign currency	(27.8)		47.9		(24.4)		86.2
Net foreign exchange (losses) gains - foreign currency translation (3)	(21.8)		9.0		(20.7)		14.0
Net foreign exchange (losses) gains - currency swaps(3)	(0.9)		3.7		1.8		6.1
Net foreign exchange (losses) - currency forwards(3)	(0.4)		(7.8)		(0.9)		(10.8)
Net foreign exchange gains - currency options(3)	0.9		—		0.8		—
Net foreign exchange gains - currency futures(3)	0.8		—		0.1		—
Income tax benefit (expense)	4.3		(0.8)		6.4		0.1
Total foreign currency remeasurement (losses) gains recognized through net (loss) income, after tax	(44.9)		52.0		(36.9)		95.6
Change in foreign currency translation on investments recognized through other comprehensive income (loss), after tax	45.1		(67.8)		44.1		(109.6)
Change in foreign currency translation on non - investment net liabilities recognized through other comprehensive income (loss), after tax	(7.6)		25.5		(13.0)		40.6
Total foreign currency translation gains (losses) recognized through other comprehensive income (loss), after tax	37.5		(42.3)		31.1		(69.0)
Total foreign currency (losses) gains recognized in comprehensive (loss) income, after tax	$	(7.4)	$	9.7	$	(5.8)	$	26.6

(1)Component of Net realized investment (losses) gains on the Consolidated Statements of (Loss) Income

(2)Component of Net unrealized investment gains (losses) on the Consolidated Statements of (Loss) Income

(3)Component of Net foreign exchange (losses) gains on the Consolidated Statements of (Loss) Income

As of September 30, 2020, the following currencies represented the largest exposure to foreign currency risk as a percentage of Sirius Group's common shareholders' equity: the SEK 4% (short) and the Japanese Yen 2% (long).

As of December 31, 2019, the following currencies represented the largest exposure to foreign currency risk as a percentage of Sirius Group's common shareholders' equity: the Japanese Yen 9% (short) and the SEK 3% (long).

Investment portfolio composition by currency

As of September 30, 2020 and December 31, 2019, Sirius Group's investment portfolio included approximately $535 million and $484 million of non-U.S. dollar denominated investments, most of which is denominated in Swedish kronor, Canadian dollar, Euro, Israeli shekel, and British pound. The investment values are impacted by changes in the exchange rate between the U.S. dollar and those currencies.

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Set forth below is the carrying value of our investment holdings in U.S. dollars and foreign currencies as of September 30, 2020 and December 31, 2019:

	Carrying Value at September 30, 2020		Carrying Value at December 31, 2019
Currency (Millions)	Local Currency	USD	Local Currency	USD
U.S. Dollar	3,103.5	$3,103.5	3,034.1	$3,034.1
Swedish kronor	1,522.0	168.8	1,513.7	162.4
Canadian dollar	110.6	82.7	113.1	87.0
Euro	66.3	77.6	78.2	87.7
Israeli shekel	172.5	50.3	264.8	76.6
British pound	14.2	18.2	8.5	11.2
Other	—	137.1	—	59.2
Total investments		$3,638.2		$3,518.2

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Results of Reportable Segments

Global Reinsurance

Global Reinsurance consists of Sirius Group's underwriting lines of business that offer Other Property, Property Catastrophe Excess Reinsurance, Agriculture Reinsurance, Aviation & Space, Marine & Energy, Trade Credit, Contingency, and Casualty Reinsurance.

	Three months ended September 30,						Nine months ended September 30,
Global Reinsurance (Millions)	2020			2019			2020			2019
Gross written premiums	$	248.2		$	256.3		$	927.0		$	1,008.4
Net written premiums	192.2			202.6			758.1			805.2
Net earned insurance and reinsurance premiums	243.5			249.5			719.4			705.7
Loss and allocated LAE	(194.5)			(261.7)			(600.2)			(558.0)
Insurance and reinsurance acquisition expenses	(51.8)			(54.3)			(156.4)			(149.9)
Technical (loss)	$	(2.8)		$	(66.5)		$	(37.2)		$	(2.2)
Unallocated LAE	(7.7)			(8.4)			(17.9)			(17.1)
Other underwriting expenses	(25.3)			(20.8)			(67.1)			(64.0)
Underwriting (loss)	$	(35.8)		$	(95.7)		$	(122.2)		$	(83.3)
Ratios:
Loss ratio(1)	83.0		%	108.3		%	85.9		%	81.5		%
Acquisition expense ratio(2)	21.3		%	21.8		%	21.7		%	21.2		%
Other underwriting expense ratio(3)	10.4		%	8.3		%	9.3		%	9.1		%
Combined ratio(4)	114.7		%	138.4		%	116.9		%	111.8		%

(1)The loss ratio is calculated by dividing the sum of loss and allocated LAE and unallocated LAE expenses by net earned insurance and reinsurance premiums.

(2)The acquisition expense ratio is calculated by dividing insurance and reinsurance acquisition expenses by net earned insurance and reinsurance premiums.

(3)The other underwriting expense ratio is calculated by dividing other underwriting expenses by net earned insurance and reinsurance premiums.

(4)The combined ratio is calculated by combining the loss ratio, the acquisition expense ratio, and the other underwriting expense ratio.

Underwriting Results

Three months ended September 30, 2020 and 2019:

Gross written premiums decreased 3% to $248 million for the three months ended September 30, 2020 from $256 million for the three months ended September 30, 2019 primarily due to a decrease in Trade Credit ($9 million). Net written premiums decreased 5% to $192 million for the three months ended September 30, 2020 from $203 million for the three months ended September 30, 2019 primarily due to the same reason for the gross written premiums decrease.

Global Reinsurance produced a net combined ratio of 115% for the three months ended September 30, 2020 compared to 138% for the three months ended September 30, 2019. The decrease in the combined ratio was driven primarily by lower catastrophe losses.

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Global Reinsurance recorded an underwriting (loss) of $(36) million for the three months ended September 30, 2020 compared to an underwriting (loss) of $(96) million for the three months ended September 30, 2019. The three months ended September 30, 2020 included COVID-19 losses of $6 million (2 points). Additionally, third quarter losses included $14 million (6 points) from the August Beirut explosion. Net unfavorable prior year loss reserve development was $1 million (less than 1 point) for the three months ended September 30, 2020. Net unfavorable prior year loss reserve development was $11 million (4 points) for the three months ended September 30, 2019 primarily driven by Other Property ($14 million), Casualty Reinsurance ($9 million), and Agriculture Reinsurance ($1 million), partially offset by net favorable prior year loss reserve development in Property Catastrophe Excess Reinsurance ($14 million). Catastrophe losses, net of reinsurance and reinstatement premiums, for the three months ended September 30, 2020 were $53 million (22 points) primarily from Hurricane Laura ($29 million), an August Midwest derecho ($11 million), and the California wildfires ($10 million). Catastrophe losses, net of reinsurance and reinstatement premiums, for the three months ended September 30, 2019, were $109 million (44 points) primarily from Typhoon Faxai ($52 million) and Hurricane Dorian ($44 million).

Nine months ended September 30, 2020 and 2019:

Gross written premiums decreased 8% to $927 million for the nine months ended September 30, 2020 from $1,008 million for the nine months ended September 30, 2019 primarily due to a decrease in Other Property ($75 million) from lower premiums on a fronting arrangement. Absent the effect of the fronting arrangement, gross written premiums increased less than 1% compared to the prior period due to an increase in Casualty Reinsurance ($19 million), Marine & Energy ($7 million), and Contingency ($7 million), partially offset by decreases in Trade Credit ($15 million) and Agriculture Reinsurance ($12 million). Net written premiums decreased 6% to $758 million for the nine months ended September 30, 2020 from $805 million for the nine months ended September 30, 2019 primarily due to decreases in Property Catastrophe Excess Reinsurance ($40 million), Agriculture Reinsurance ($12 million), and Trade Credit ($15 million), partially offset by an increase in Casualty Reinsurance ($18 million). The reduction in Property Catastrophe Excess Reinsurance was due to increased retrocessional protections as the Company took actions to reduce catastrophic risk. The Other Property fronting arrangement did not impact net written or earned insurance and reinsurance premiums for either the 2020 or 2019 periods.

Global Reinsurance produced a net combined ratio of 117% for the nine months ended September 30, 2020 compared to 112% for the nine months ended September 30, 2019. The increase in the combined ratio was driven by COVID-19 losses, partially offset by lower net unfavorable prior year loss reserve development and catastrophe losses.

Global Reinsurance recorded an underwriting (loss) of $(122) million for the nine months ended September 30, 2020 compared to an underwriting (loss) of $(83) million for the nine months ended September 30, 2019. The nine months ended September 30, 2020 included COVID-19 losses of $136 million (19 points) in Contingency ($47 million), Property Catastrophe Excess Reinsurance ($37 million), Other Property ($35 million), Trade Credit ($12 million), Casualty Reinsurance ($4 million), and Marine & Energy ($1 million). Additionally, losses for the nine months ended September 30. 2020 included $14 million (2 points) from the August Beirut explosion. Net unfavorable prior year loss reserve development was $15 million (2 points) for the nine months ended September 30, 2020 as unfavorable prior year loss reserve development in Other Property ($22 million), Aviation & Space ($10 million), and Casualty Reinsurance ($9 million) was partially offset by favorable prior year loss reserve development in Property Catastrophe Excess Reinsurance ($23 million). Net unfavorable prior year loss reserve development was $83 million (12 points) for the nine months ended September 30, 2019 mainly due to unfavorable prior year loss reserve development in Other Property ($53 million), Property Catastrophe Excess Reinsurance ($14 million), and Casualty Reinsurance ($11 million). The unfavorable prior year loss reserve development in Other Property and Property Catastrophe Excess Reinsurance was primarily due to higher losses from recent accident years mainly Typhoon Jebi and Hurricanes Michael, Florence and Irma. Catastrophe losses, net of reinsurance and reinstatement premiums, for the nine months ended September 30, 2020 were $72 million (10 points) compared to $119 million (17 points) for the nine months ended September 30, 2019. Catastrophe losses, net of reinsurance and reinstatement premiums, for the nine months ended September 30, 2020 were primarily from Hurricane Laura ($29 million), an August Midwest derecho ($11 million), and the California wildfires ($10 million). Catastrophe losses, net of reinsurance and reinstatement premiums, for the nine months ended September 30, 2019 were primarily from Typhoon Faxai ($52 million) and Hurricane Dorian ($44 million).

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Global Reinsurance gross written premiums

	Three months ended September 30,				Nine months ended September 30,
Global Reinsurance (Millions)	2020		2019		2020		2019
Other Property	$	107.4	$	103.6	$	297.4	$	371.9
Casualty Reinsurance	63.3		63.5		178.5		159.6
Property Catastrophe Excess Reinsurance	41.4		42.3		281.2		286.4
Aviation & Space	17.0		20.4		47.2		54.8
Marine & Energy	8.1		6.1		34.1		27.0
Agriculture Reinsurance	4.8		8.0		51.3		63.2
Contingency	3.3		0.9		10.6		4.0
Trade Credit	2.9		11.5		26.7		41.5
Total	$	248.2	$	256.3	$	927.0	$	1,008.4

Three months ended September 30, 2020 and 2019:

Global Reinsurance's gross written premiums decreased 3% to $248 million for the three months ended September 30, 2020 from $256 million for the three months ended September 30, 2019 primarily due to a decrease in Trade Credit ($9 million).

Nine months ended September 30, 2020 and 2019:

Global Reinsurance's gross written premiums decreased 8% to $927 million for the nine months ended September 30, 2020 from $1,008 million for the nine months ended September 30, 2019. The decrease in Other Property ($75 million) was due to lower premium volume on a fronting arrangement. Absent the effect of the fronting arrangement, gross written premiums increased by less than 1% compared to the prior period primarily due to increases in Casualty Reinsurance ($19 million), Marine & Energy ($7 million), and Contingency ($7 million), partially offset by decreases in Trade Credit ($15 million) and Agriculture Reinsurance ($12 million).

Global Reinsurance net earned insurance and reinsurance premiums

	Three months ended September 30,				Nine months ended September 30,
Global Reinsurance (Millions)	2020		2019		2020		2019
Other Property	$	89.1	$	86.8	$	260.3	$	268.2
Casualty Reinsurance	56.2		50.8		163.1		132.3
Property Catastrophe Excess Reinsurance	46.5		49.4		140.7		145.4
Aviation & Space	16.9		18.0		51.5		46.9
Agriculture Reinsurance	15.9		23.8		41.8		51.1
Trade Credit	9.3		12.7		33.1		34.7
Marine & Energy	6.6		6.6		20.1		22.8
Contingency	3.0		1.4		8.8		4.3
Total	$	243.5	$	249.5	$	719.4	$	705.7

Three months ended September 30, 2020 and 2019:

Global Reinsurance's net earned insurance and reinsurance premiums decreased 2% to $244 million for the three months ended September 30, 2020 from $250 million for the three months ended September 30, 2019 primarily due to a decrease in Agriculture Reinsurance ($8 million).

Nine months ended September 30, 2020 and 2019:

Global Reinsurance's net earned insurance and reinsurance premiums increased 2% to $719 million for the nine months ended September 30, 2020 from $706 million for the nine months ended September 30, 2019 primarily due to an increase in Casualty Reinsurance ($31 million), partially offset by a decrease in Agriculture Reinsurance ($9 million). The Other Property fronting arrangement did not impact net earned insurance and reinsurance premiums for either the 2020 or 2019 periods.

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Global A&H

Global A&H consists of Sirius Group's Global A&H insurance and reinsurance underwriting business along with IMG and Armada, which provide supplemental healthcare and medical travel insurance products as well as related administration services.

	Three months ended September 30,						Nine months ended September 30,
Global A&H (Millions)	2020			2019			2020			2019
Gross written premiums	$	88.8		$	137.4		$	434.6		$	459.5
Net written premiums	72.2			104.6			334.9			360.1
Net earned insurance and reinsurance premiums	114.3			115.1			345.4			330.0
Loss and allocated LAE	(84.6)			(63.6)			(234.5)			(198.6)
Insurance and reinsurance acquisition expenses	(36.6)			(32.5)			(98.9)			(95.1)
Technical (loss) profit	$	(6.9)		$	19.0		$	12.0		$	36.3
Unallocated LAE	(0.5)			(2.0)			(2.8)			(5.5)
Other underwriting expenses	(5.7)			(6.8)			(18.0)			(18.8)
Underwriting (loss) income	$	(13.1)		$	10.2		$	(8.8)		$	12.0
Service fee revenue	26.3			31.0			85.3			97.6
MGU unallocated LAE	(5.8)			(4.3)			(18.0)			(13.7)
MGU other underwriting expenses	(4.7)			(3.7)			(14.4)			(11.2)
MGU general and administrative expenses	(11.0)			(15.1)			(36.2)			(46.3)
Underwriting (loss) income, including net service fee income	$	(8.3)		$	18.1		$	7.9		$	38.4
Ratios:
Loss ratio(1)	74.5		%	57.0		%	68.7		%	61.8		%
Acquisition expense ratio(2)	32.0		%	28.2		%	28.6		%	28.8		%
Other underwriting expense ratio(3)	5.0		%	5.9		%	5.2		%	5.7		%
Combined ratio(4)	111.5		%	91.1		%	102.5		%	96.3		%

(1)The loss ratio is calculated by dividing the sum of loss and allocated LAE and unallocated LAE expenses by net earned insurance and reinsurance premiums.

(2)The acquisition expense ratio is calculated by dividing insurance and reinsurance acquisition expenses by net earned insurance and reinsurance premiums.

(3)The other underwriting expense ratio is calculated by dividing other underwriting expenses by net earned insurance and reinsurance premiums.

(4)The combined ratio is calculated by combining the loss ratio, the acquisition expense ratio, and the other underwriting expense ratio.

Underwriting Results

Three months ended September 30, 2020 and 2019:

Gross written premiums decreased 35% to $89 million for the three months ended September 30, 2020 from $137 million for the three months ended September 30, 2019 due to reduced premium volume for travel medical and trip cancellation insurance. Net written premiums decreased 31% to $72 million for the three months ended September 30, 2020 from $105 million for the three months ended September 30, 2019 due to the same reasons as the gross written premiums decrease.

Global A&H produced a net combined ratio of 112% for the three months ended September 30, 2020 compared to 91% for the three months ended September 30, 2019. The three months ended September 30, 2020 included COVID-19 losses of $31 million (27 points), primarily from contracts covering infectious disease related expenses. Net favorable prior year loss reserve development was insignificant for the three months ended September 30, 2020 compared to net favorable prior year loss reserve development of $6 million (5 points) for the three months ended September 30, 2019. Additionally, attritional losses were lower for the three months ended September 30, 2020 due to lower medical utilization.

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Underwriting (loss) income, including net service fee income, for Global A&H was $(8) million for the three months ended September 30, 2020 compared to $18 million of underwriting income for the three months ended September 30, 2019. The decrease of $26 million was driven by COVID-19 losses and lower net service fee income. For the three months ended September 30, 2020 and 2019, underwriting income, including net service fee income, included net losses of $1 million and $2 million relating to ArmadaHealth, LLC, respectively.

Nine months ended September 30, 2020 and 2019:

Gross written premiums decreased 5% to $435 million for the nine months ended September 30, 2020 from $460 million for the nine months ended September 30, 2019 due to reduced premium volume for travel medical and trip cancellation insurance, partially offset by higher writings for risks primarily originating from the U.S. Net written premiums decreased 7% to $335 million for the nine months ended September 30, 2020 from $360 million for the nine months ended September 30, 2019 due to the same reasons as the gross written premiums decrease.

Global A&H produced a net combined ratio of 103% for the nine months ended September 30, 2020 compared to 96% for the nine months ended September 30, 2019. The nine months ended September 30, 2020 included COVID-19 losses of $53 million (15 points). Net favorable prior year loss reserve development was $8 million (2 points) for the nine months ended September 30, 2020 compared to net favorable prior year loss reserve development of $1 million (less than 1 point) for the nine months ended September 30, 2019.

Underwriting income, including net service fee income, for Global A&H was $8 million for the nine months ended September 30, 2020 compared to $38 million for the nine months ended September 30, 2019. The decrease of $30 million was driven by COVID-19 losses and lower net service fee income, partially offset by higher favorable loss reserve development for the nine months ended September 30, 2020. For each of the nine months ended September 30, 2020 and 2019, underwriting (loss) income, including net service fee income, included net losses of $4 million relating to ArmadaHealth, LLC.

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U.S. Specialty

U.S. Specialty consists of Sirius Group's specialty insurance product offerings, which includes Environmental, Surety, and Workers’ Compensation. In April 2020, the Company decided to exit the Surety business due to competitive market conditions in that business line and the recent economic downturn which presented new risks and challenges for this line of business.

	Three months ended September 30,						Nine months ended September 30,
U.S. Specialty (Millions)	2020			2019			2020			2019
Gross written premiums	$	22.6		$	17.9		$	68.9		$	50.5
Net written premiums	20.5			14.3			59.5			42.0
Net earned insurance premiums	17.2			9.1			45.2			19.9
Loss and allocated LAE	(11.1)			(8.2)			(29.2)			(14.7)
Insurance acquisition expenses	(4.0)			(2.0)			(10.4)			(4.5)
Technical profit (loss)	$	2.1		$	(1.1)		$	5.6		$	0.7
Unallocated LAE	(0.2)			(0.1)			(0.4)			(0.2)
Other underwriting expenses	(4.3)			(2.7)			(12.4)			(7.6)
Underwriting (loss)	$	(2.4)		$	(3.9)		$	(7.2)		$	(7.1)
Ratios:
Loss ratio(1)	65.7		%	91.2		%	65.5		%	74.9		%
Acquisition expense ratio(2)	23.3		%	22.0		%	23.0		%	22.6		%
Other underwriting expense ratio(3)	25.0		%	29.7		%	27.4		%	38.2		%
Combined ratio(4)	114.0		%	142.9		%	115.9		%	135.7		%

(1)The loss ratio is calculated by dividing the sum of loss and allocated LAE and unallocated LAE expenses by net earned insurance premiums.

(2)The acquisition expense ratio is calculated by dividing insurance acquisition expenses by net earned insurance premiums.

(3)The other underwriting expense ratio is calculated by dividing other underwriting expenses by net earned insurance premiums.

(4)The combined ratio is calculated by combining the loss ratio, the acquisition expense ratio, and the other underwriting expense ratio.

Underwriting Results

Three months ended September 30, 2020 and 2019:

Gross written premiums increased 28% to $23 million for the three months ended September 30, 2020 from $18 million for the three months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($8 million). Net written premiums increased 50% to $21 million for the three months ended September 30, 2020 from $14 million for the three months ended September 30, 2019 due to an increase in Workers' Compensation ($8 million). The increase in Workers' Compensation is due to business written through Pie Insurance, a start-up specializing in a data driven approach to workers' compensation insurance, where we also have a minority investment and carrier relationship.

U.S. Specialty recorded an underwriting (loss) of $(2) million for the three months ended September 30, 2020 compared to an underwriting (loss) of $(4) million for the three months ended September 30, 2019.

Nine months ended September 30, 2020 and 2019:

Gross written premiums increased 35% to $69 million for the nine months ended September 30, 2020 from $51 million for the nine months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($22 million). Net written premiums increased 43% to $60 million for the nine months ended September 30, 2020 from $42 million for the nine months ended September 30, 2019 due to an increase in Workers' Compensation ($19 million). The increase in Workers' Compensation is due to business written through Pie Insurance.

U.S. Specialty recorded an underwriting (loss) of $(7) million for each of the nine months ended September 30, 2020 and 2019.

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U.S. Specialty gross written premiums

	Three months ended September 30,				Nine months ended September 30,
U.S. Specialty (Millions)	2020		2019		2020		2019
Workers' Compensation	$	18.6	$	10.6	$	54.1	$	32.4
Environmental	3.2		4.8		11.9		13.1
Surety	0.8		2.5		2.9		5.0
Total	$	22.6	$	17.9	$	68.9	$	50.5

Three months ended September 30, 2020 and 2019:

Gross written premiums increased 28% to $23 million for the three months ended September 30, 2020 from $18 million for the three months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($8 million). The increase in Workers' Compensation is due to business written through Pie Insurance.

Nine months ended September 30, 2020 and 2019:

Gross written premiums increased 35% to $69 million for the nine months ended September 30, 2020 from $51 million for the nine months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($22 million). The increase in Workers' Compensation is due to business written through Pie Insurance.

U.S. Specialty net earned insurance premiums

	Three months ended September 30,				Nine months ended September 30,
U.S. Specialty (Millions)	2020		2019		2020		2019
Workers' Compensation	$	14.7	$	6.8	$	36.4	$	13.9
Environmental	1.6		1.0		4.6		2.4
Surety	0.9		1.3		4.2		3.6
Total	$	17.2	$	9.1	$	45.2	$	19.9

Three months ended September 30, 2020 and 2019:

Net earned insurance premiums increased 89% to $17 million for the three months ended September 30, 2020 from $9 million for the three months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($8 million). The increase in Workers' Compensation is due to business written through Pie Insurance.

Nine months ended September 30, 2020 and 2019:

Net earned insurance premiums increased 125% to $45 million for the nine months ended September 30, 2020 from $20 million for the nine months ended September 30, 2019 primarily due to an increase in Workers' Compensation ($22 million). The increase in Workers' Compensation is due to business written through Pie Insurance.

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Runoff & Other

Runoff & Other consists of the results of Sirius Global Solutions, which specializes in the acquisition and management of runoff liabilities for insurance and reinsurance companies, both in the United States and internationally, as well as asbestos risks, environmental risks and other long-tailed liability exposures.

	Three months ended September 30,				Nine months ended September 30,
Runoff & Other (Millions)	2020		2019		2020		2019
Gross written premiums	$	(3.6)	$	2.1	$	65.7	$	4.7
Net written premiums	(2.6)		0.8		65.7		1.5
Net earned insurance and reinsurance premiums	(2.4)		0.5		67.1		1.2
Loss and allocated LAE	(1.1)		(0.9)		(61.2)		(4.4)
Insurance and reinsurance acquisition expenses	(0.8)		(0.1)		(0.9)		(2.6)
Technical (loss) profit	$	(4.3)	$	(0.5)	$	5.0	$	(5.8)
Unallocated LAE	(1.0)		(0.2)		(11.8)		(0.9)
Other underwriting expenses	(1.3)		(1.4)		(3.7)		(4.6)
Underwriting (loss)	$	(6.6)	$	(2.1)	$	(10.5)	$	(11.3)
Service fee revenue	0.9		—		0.9		—
General and administrative expenses	(0.9)		(1.2)		(3.8)		(3.0)
Underwriting (loss), including net service fee income	$	(6.6)	$	(3.3)	$	(13.4)	$	(14.3)

Underwriting Results

Three months ended September 30, 2020 and 2019:

Runoff & Other recorded $(4) million of gross written premiums for the three months ended September 30, 2020 compared to $2 million of gross written premiums for the three months ended September 30, 2019. The reduction in gross written for the three months ended September 30, 2020 was due to a return of premium related to a runoff contract based on updated information from the client.

Runoff & Other recorded an underwriting (loss), including net service fee income, of $(7) million for the three months ended September 30, 2020 compared to an underwriting (loss), including net service fee income, of $(3) million for the three months ended September 30, 2019. Runoff & Other recorded less than $1 million of net favorable prior year loss reserve development for the three months ended September 30, 2020 compared to $1 million of net unfavorable prior year loss reserve development for the three months ended September 30, 2019. For the three months ended September 30, 2020, underwriting (loss) income, including net service fee income, included a $1 million gain on the sale of Empire to Physicians' Reciprocal Insurers. See "Overview - Background and Recent Developments - Empire Insurance Company" for further details on the sale of Empire.

Nine months ended September 30, 2020 and 2019:

Runoff & Other recorded $66 million of gross written premiums for the nine months ended September 30, 2020 compared to $5 million of gross written premiums for the nine months ended September 30, 2019. The increase from the prior period was primarily due to premiums from the LPT. The LPT did not have an impact on net underwriting results as net earned insurance and reinsurance premiums were offset by a corresponding losses incurred amount. See "Overview - Background and Recent Developments - Loss Portfolio Transfer" for further details on the LPT.

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Runoff & Other recorded an underwriting (loss), including net service fee income, of $(13) million for the nine months ended September 30, 2020 compared to an underwriting (loss), including net service fee income, of $(14) million for the nine months ended September 30, 2019. Runoff & Other recorded an insignificant amount of net unfavorable prior year loss reserve development for the nine months ended September 30, 2020 compared to $5 million of net unfavorable prior year loss reserve development for the nine months ended September 30, 2019. The net unfavorable prior year loss reserve development for the nine months ended September 30, 2019 was primarily due to an increase in reserves for a disputed Latin American Facultative Surety claim in arbitration. For the nine months ended September 30, 2020, underwriting (loss) income, including net service fee income, included a $1 million gain on the sale of Empire to Physicians' Reciprocal Insurers. See "Overview - Background and Recent Developments - Empire Insurance Company" for further details on the sale of Empire.

Reinsurance Protection

The following tables display Sirius Group's underwriting ratios prior to cessions to reinsurers ("Gross"), cessions to reinsurers ("Ceded"), and after cessions to reinsurers ("Net") basis.

Three months ended September 30, 2020 and 2019

	Three months ended September 30, 2020
	Global Reinsurance	Global A&H	U.S. Specialty	Total
Gross ratios:
Loss ratio	83.1%	71.8%	54.4%	79.1%
Acquisition expense ratio	20.9%	26.8%	21.2%	21.7%
Other underwriting expense ratio	8.3%	3.6%	19.3%	8.0%
Gross Combined ratio	112.3%	102.2%	94.9%	108.8%
Ceded ratios:
Loss ratio	83.3%	69.6%	16.2%	69.2%
Acquisition expense ratio	19.4%	21.3%	12.4%	20.3%
Ceded Combined ratio	102.7%	90.9%	28.6%	89.5%
Net ratios:
Loss ratio	83.0%	74.5%	65.7%	82.0%
Acquisition expense ratio	21.3%	32.0%	23.3%	22.4%
Other underwriting expense ratio	10.4%	5.0%	25.0%	11.1%
Net Combined ratio	114.7%	111.5%	114.0%	115.5%

Sirius Group's net combined ratio was 7 points higher than the gross combined ratio primarily due to the costs of retrocessional protections with limited ceded loss recoveries for the three months ended September 30, 2020, driven mainly by Global Reinsurance.

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	Three months ended September 30, 2019
	Global Reinsurance	Global A&H	U.S. Specialty	Total
Gross ratios:
Loss ratio	101.8%	56.2%	112.3%	88.7%
Acquisition expense ratio	22.1%	26.8%	14.9%	20.5%
Other underwriting expense ratio	6.5%	4.6%	27.2%	7.4%
Gross Combined ratio	130.4%	87.6%	154.4%	116.6%
Ceded ratios:
Loss ratio	79.1%	53.3%	238.0%	72.7%
Acquisition expense ratio	22.2%	21.9%	26.9%	22.2%
Ceded Combined ratio	101.3%	75.2%	264.9%	94.9%
Net ratios:
Loss ratio	108.3%	57.0%	91.2%	93.2%
Acquisition expense ratio	21.8%	28.2%	22.0%	20.1%
Other underwriting expense ratio	8.3%	5.9%	29.7%	9.5%
Net Combined ratio	138.4%	91.1%	142.9%	122.8%

Sirius Group’s net combined ratio was 6 points higher than the gross combined ratio primarily due to the costs of retrocessional protections with limited ceded loss recoveries for the three months ended September 30, 2019, driven mainly by Global Reinsurance.

Nine months ended September 30, 2020 and 2019

	Nine months ended September 30, 2020
	Global Reinsurance	Global A&H	U.S. Specialty	Total
Gross ratios:
Loss ratio	87.7%	68.2%	61.2%	82.6%
Acquisition expense ratio	21.0%	26.8%	22.7%	19.9%
Other underwriting expense ratio	7.7%	3.9%	29.6%	8.0%
Gross Combined ratio	116.4%	98.9%	113.5%	110.5%
Ceded ratios:
Loss ratio	96.3%	67.5%	35.6%	82.8%
Acquisition expense ratio	17.2%	21.0%	21.3%	18.9%
Ceded Combined ratio	113.5%	88.5%	56.9%	101.7%
Net ratios:
Loss ratio	85.9%	68.7%	65.5%	82.6%
Acquisition expense ratio	21.7%	28.6%	23.0%	20.1%
Other underwriting expense ratio	9.3%	5.2%	27.4%	9.8%
Net Combined ratio	116.9%	102.5%	115.9%	112.5%

Sirius Group's net combined ratio was 2 points higher than the gross combined ratio for the nine months ended September 30, 2020. An Other Property fronting arrangement, which records offsetting gross and ceded loss and commission results, less a margin to Sirius Group, also impacted the gross and ceded loss and commission ratios for the nine months ended September 30, 2020.

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	Nine months ended September 30, 2019
	Global Reinsurance	Global A&H	U.S. Specialty	Total
Gross ratios:
Loss ratio	76.4%	61.7%	79.7%	72.9%
Acquisition expense ratio	22.3%	27.3%	25.2%	21.4%
Other underwriting expense ratio	7.1%	4.3%	33.1%	7.8%
Gross Combined ratio	105.8%	93.3%	138.0%	102.1%
Ceded ratios:
Loss ratio	58.0%	61.2%	106.8%	59.8%
Acquisition expense ratio	26.6%	22.3%	24.1%	25.1%
Ceded Combined ratio	84.6%	83.5%	130.9%	84.9%
Net ratios:
Loss ratio	81.5%	61.8%	74.9%	76.7%
Acquisition expense ratio	21.2%	28.8%	22.6%	20.4%
Other underwriting expense ratio	9.1%	5.7%	38.2%	10.0%
Net Combined ratio	111.8%	96.3%	135.7%	107.1%

Sirius Group's net combined ratio was 5 points higher than the gross combined ratio primarily due to the costs of retrocessional protections with limited ceded loss recoveries for the nine months ended September 30, 2019, driven mainly by Global Reinsurance.

Non-GAAP Financial Measures

In presenting Sirius Group’s results, management has included and discussed non-GAAP financial measures:  Tangible book value, Tangible book value per common share, and Operating (loss) attributable to common shareholders. The Company believes that these non-GAAP financial measures, which may be defined and calculated differently by other companies, better explain and enhance the understanding of the Company’s results of operations. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP.

Tangible book value and Tangible book value per common share

Tangible book value and Tangible book value per common share are non-GAAP financial measures. Tangible book value and Tangible book value per common share are useful to investors because they measure the realizable value of common shareholder returns, excluding the impact of goodwill, intangible assets, and net deferred liability on intangible assets.

Tangible book value is derived by subtracting Goodwill, Intangible assets and Net deferred tax liability on intangible assets from book value. Tangible book value per common share is derived by dividing Tangible book value by the total number of Common shares outstanding.

The reconciliations to Total common shareholders’ equity and Book value per common share, the most directly comparable GAAP measures, are presented in the table below.

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	September 30,		June 30,		December 31,
(Expressed in millions of U.S. dollars, except share and per share amounts)	2020		2020		2019
Common shares outstanding	115,299,341		115,299,341		115,299,341
Total common shareholders’ equity	$	1,459.2	$	1,519.7	$	1,640.4
Goodwill	(400.8)		(400.8)		(400.8)
Intangible assets	(168.0)		(171.9)		(179.8)
Net deferred tax liability on intangible assets	19.1		20.1		22.8
Tangible book value	$	909.5	$	967.1	$	1,082.6
Book value per common share	$	12.66	$	13.18	$	14.23
Tangible book value per common share	$	7.89	$	8.39	$	9.39

Operating (loss) attributable to common shareholders

The Company uses Operating (loss) attributable to common shareholders as a measure to evaluate the underlying fundamentals of its operations and believes it to be a useful measure of its core performance. Operating (loss) attributable to common shareholders as used herein differs from net (loss) income attributable to common shareholders, which the Company believes is the most directly comparable GAAP measure, by the exclusion of net realized and unrealized gains and losses on investments, net foreign exchange gains (losses) and the associated income tax expense or benefit. The Company’s management believes that Operating (loss) attributable to common shareholders is useful to investors because it is more reflective of the Company’s core business, as it removes the variability arising from fluctuations in the Company’s fixed maturity investment portfolio, equity investments trading, investments-related derivatives, and net foreign exchange gains (losses) and the associated income tax expense or benefit of those fluctuations. The following is a reconciliation of Net (loss) income attributable to common shareholders to Operating (loss) attributable to common shareholders:

(Expressed in millions of U.S. dollars)	Three months ended September 30,				Nine months ended September 30,
	2020		2019		2020		2019
Net (loss) income attributable to common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	99.2
Adjustment for net realized and unrealized (gains) on investments	(27.4)		(69.2)		(19.7)		(183.3)
Adjustment for net foreign exchange losses (gains)	21.3		(4.3)		18.9		(9.4)
Adjustment for income tax expense (benefits) (1)	0.8		10.8		(10.2)		27.6
Operating (loss) attributable to common shareholders	$	(100.8)	$	(65.4)	$	(218.2)	$	(65.9)

(1)Adjustment for income tax expense (benefits) represents the income tax expense (benefits) associated with the adjustment for net realized and unrealized (gains) on investments and the income tax expense (benefits) associated with the adjustment for net foreign exchange losses (gains). The income tax impact is estimated by applying the statutory rates of applicable jurisdictions, after consideration of other relevant factors.

Liquidity and Capital Resources

Liquidity is a measure of a company's ability to generate cash flows sufficient to meet short-term and long-term cash requirements of its business operations. Sirius Group's insurance and reinsurance operations are subject to regulation and supervision in each of the jurisdictions where they are domiciled and licensed to conduct business. Generally, regulatory authorities have broad supervisory and administrative powers over such matters as licenses, standards of solvency, premium rates, policy forms, investments, security deposits, methods of accounting, form and content of financial statements, reserves for unpaid loss and LAE, reinsurance, minimum capital and surplus requirements, dividends and other distributions to shareholders, periodic examinations and annual and other report filings. In general, such regulation is for the protection of policyholders rather than shareholders. Sirius Group manages its liquidity needs primarily through the maintenance of a short duration and high quality fixed income portfolio.

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To date, the COVID-19 pandemic has not materially impacted our ability to meet liquidity, regulatory capital requirements, or other contractual commitments.

Dividend Capacity

Sirius Group's top tier regulated insurance and reinsurance operating subsidiary is Sirius Bermuda. Sirius Bermuda's ability to pay dividends is limited under Bermuda law and regulations. Under the Insurance Act 1978, Sirius Bermuda is restricted with respect to the payment of dividends. Sirius Bermuda is prohibited from declaring or paying in any financial year dividends of more than 25% of its total statutory capital and surplus (as shown on its previous financial year's statutory balance sheet) unless it files, at least seven days before payment of such dividends, with the Bermuda Monetary Authority ("BMA") an affidavit stating that it will continue to meet the required margins following the declaration of those dividends. As of December 31, 2019, Sirius Bermuda could pay approximately $524 million to its parent company, Sirius International Group, Ltd., during 2020. Sirius Bermuda indirectly owns Sirius International, Sirius America and Sirius Group's other insurance and reinsurance operating companies, each of which are limited in their ability to pay dividends by the insurance laws of their relevant jurisdictions. CMIG International, which is approximately 82% owned by China Minsheng Investment Group Corp., Ltd. ("CMIG"), shares approximately 87% of the voting and dispositive power over the Sirius Group equity securities as of September 30, 2020, with CMIG, and CMIG International's wholly-owned Bermuda holding company, CM Bermuda Ltd. ("CM Bermuda"). During 2019, CMIG made several public announcements relating to defaults and cross-defaults on certain bonds and other debt obligations issued by certain subsidiaries of CMIG (the "CMIG Defaults"), the failure and uncertainty of CMIG's subsidiaries to repay their debt obligations as they become due and the existence of certain asset freeze orders relating to the equity interests of CMIG in certain Chinese subsidiaries not within the chain of control of Sirius Group. On May 3, 2019, in connection with the CMIG Defaults, Sirius Bermuda and Sirius Group entered into a voluntary undertaking with the BMA to provide further comfort to the BMA as the group supervisor of Sirius Group and primary regulator of Sirius Bermuda, the designated insurer for group supervisory purposes regarding the potential risks to Sirius Group in connection with the CMIG Defaults. On March 27, 2020, Sirius Group extended the voluntary undertaking for an additional year. Pursuant to the voluntary undertaking, each of Sirius Group and Sirius Bermuda have agreed, until May 3, 2021, (a) to provide ten days prior written notice to the BMA prior to declaring any dividend or capital distribution, which notice shall include an affidavit confirming that the declaration and payment of such dividend would not be in breach of (i) the provisions of section 54 of the Companies Act 1981 in the case of Sirius Bermuda, (ii) the Minimum Liquidity Ratio as defined in the Insurance Act 1978 in the case of Sirius Bermuda; and (iii) the Target Capital Level of 120% of the Enhanced Capital Requirement as defined by the Bermuda Solvency Capital Requirement promulgated by the BMA for Sirius Group and Sirius Bermuda, and a summary description of the use proceeds from such declaration or dividend or capital distribution within Sirius Group or Sirius Bermuda; (b) not to enter into any guarantees, keepwells, loans or other financial arrangements between Sirius Group and CMIG, or provide any credit support with respect to any obligations of CMIG; and (c) not to enter into any related party transaction with CMIG without the BMA's consent. For the nine months ended September 30, 2020, Sirius Bermuda paid $70 million of dividends to its immediate parent.

Sirius International has the ability to pay dividends to its immediate parent subject to the availability of unrestricted equity, calculated in accordance with the Swedish Act on Annual Accounts in Insurance Companies and the Swedish Financial Supervisory Authority (the "SFSA"). Unrestricted equity is calculated on a consolidated group account basis and on a parent account basis. Differences between the two include but are not limited to accounting for goodwill, subsidiaries (with parent accounts stated at original foreign exchange rates), taxes and pensions. Sirius International's ability to pay dividends is limited to the "lower of" unrestricted equity as calculated within the group and parent accounts. As of December 31, 2019, Sirius International had $402 million (based on the December 31, 2019 SEK to USD exchange rate) of unrestricted equity on a parent account basis (the lower of the two approaches) available to pay dividends in 2020. The amount of dividends available to be paid by Sirius International in any given year is also subject to cash flow and earnings generated by Sirius International's business, the maintenance of adequate solvency capital ratios for Sirius International and the consolidated Sirius International UK Holdings Ltd. group, as well as dividends received from its subsidiaries. Earnings generated by Sirius International's business that are allocated to the Safety Reserve are not available to pay dividends (see "Safety Reserve" below). For the nine months ended September 30, 2020, Sirius International did not declare a dividend and paid $9 million of dividends declared prior to 2018.

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Under the normal course of business, Sirius America has the ability to pay dividends to its immediate parent during any twelve-month period without the prior approval of regulatory authorities in an amount set by a formula based on the lesser of net investment income, as defined by statute, or 10% of statutory surplus, in both cases as most recently reported to regulatory authorities, subject to the availability of earned surplus and subject to dividends paid in prior periods. Based on this formula, Sirius America has ordinary dividend capacity as of September 30, 2020 without prior regulatory approval. As of December 31, 2019, Sirius America had $522 million of statutory surplus and $89 million of earned surplus and could pay approximately $52 million to its parent company, Sirius International Holding Company, during 2020. For the nine months ended September 30, 2020, Sirius America paid a dividend of $25 million to its immediate parent.

For the nine months ended September 30, 2020, Sirius Group did not pay any dividends. As of September 30, 2020, Sirius Group had $42 million of net unrestricted cash, short-term investments, and fixed maturity investments outside of its regulated and unregulated insurance and reinsurance operating subsidiaries.

Safety Reserve

Subject to certain limitations under Swedish law, Sirius International is permitted to transfer pre-tax income amounts into a reserve referred to as a "Safety Reserve." Under local statutory requirements, an amount equal to the deferred tax liability on Sirius International's Safety Reserve is included in Solvency Capital. Access to the Safety Reserve is restricted to cover insurance and reinsurance losses and to cover a breach of the Solvency Capital Requirement. Access for any other purpose requires the approval of Swedish regulatory authorities. Similar to the approach taken by Swedish regulatory authorities, most major rating agencies generally include the balance of the Safety Reserve, without any provision for deferred taxes, in Sirius International's regulatory capital when assessing Sirius International and Sirius Group's financial strength.

As of September 30, 2020, Sirius International's Safety Reserve amounted to SEK 10.2 billion, or $1.1 billion (based on the September 30, 2020 SEK to USD exchange rate). Under GAAP, an amount equal to the Safety Reserve, net of a related deferred tax liability established at the Swedish tax rate, is classified as common shareholders' equity. Generally, this deferred tax liability ($234 million based on the September 30, 2020 SEK to USD exchange rate) is only required to be paid by Sirius International if it fails to maintain prescribed levels of premium writings and loss reserves in future years. As a result of the indefinite deferral of these taxes, the related deferred tax liability is not taken into account by Swedish regulatory authorities for purposes of calculating Solvency Capital under Swedish insurance regulations.

Pursuant to tax legislation effective as of January 1, 2019, the tax rate applicable to Swedish corporations decreased to 21.4%, and then will further reduce to 20.6% starting in 2021. The tax legislation also introduced an annual tax on the Safety Reserve effective as of January 1, 2019. This provision adds additional taxable income for the Company annually. The calculation applies the Government Borrowing Rate (with a floor rate of +0.5%) to the Safety Reserve balance at the beginning of the year. At the current year tax rate of 21.4% the additional tax expense for the nine months ended September 30, 2020 is SEK 8 million, or $1 million (based on the September 30, 2020 SEK to USD exchange rate).

Further, the enacted legislation also included a new provision treating an amount equal to 6% of the Safety Reserve balance as of January 1, 2021, as additional taxable income in tax year 2021 only, subject to tax at the applicable 20.6% rate. Based on this provision and Sirius International's Safety Reserve balance as of September 30, 2020, Sirius International has recorded an additional deferred tax liability as of September 30, 2020 in the amount of SEK 126 million, or $14 million (based on the September 30, 2020 SEK to USD exchange rate) for a total deferred tax liability of $248 million.

Insurance Float

Insurance float is an important aspect of Sirius Group's insurance and reinsurance operations. Insurance float represents funds that an insurance or reinsurance company holds for a limited time. In an insurance or reinsurance operation, float arises because premiums are collected before losses are paid. This interval can extend over many years. During that time, the insurer or reinsurer invests the funds. When the premiums that an insurer or reinsurer collects do not cover the losses and expenses it eventually must pay, the result is an underwriting loss, which can be considered as the cost of insurance float.

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Insurance float can increase in a number of ways, including through acquisitions of insurance and reinsurance operations, organic growth in existing insurance and reinsurance operations and recognition of losses that do not immediately cause a corresponding reduction in investment assets. Conversely, insurance float can decrease in a number of other ways, including sales of insurance and reinsurance operations, shrinking or runoff of existing insurance and reinsurance operations, the acquisition of operations that do not have substantial investment assets (e.g., an agency) and the recognition of gains that do not cause a corresponding increase in investment assets. It is Sirius Group's intention to generate low-cost float over time through a combination of acquisitions and organic growth in its existing insurance and reinsurance operations.

Certain operational leverage metrics can be measured with ratios that are calculated using insurance float. There are many activities that do not change the amount of insurance float at an insurance or reinsurance company but can have a significant impact on Sirius Group's operational leverage metrics. For example, investment gains and losses, foreign currency translation gains and losses, debt issuances and repurchases/repayments, common and preference share issuances and repurchases and dividends paid to shareholders are all activities that do not change insurance float but can meaningfully impact operational leverage metrics that are calculated using insurance float. Insurance float increased by $297 million from December 31, 2019 mainly due to losses incurred from COVID-19 for the nine months ended September 30, 2020.

The following table illustrates Sirius Group's consolidated insurance float position as of September 30, 2020 and December 31, 2019:

(Expressed in millions of U.S. dollars, except multiples)	September 30, 2020			December 31, 2019
Loss and LAE reserves	$	2,672.9		$	2,331.5
Unearned insurance and reinsurance premiums	759.4			708.0
Ceded reinsurance payable	270.3			244.7
Funds held under reinsurance treaties	156.5			169.1
Deferred tax liability on safety reserve	247.5			239.4
Float liabilities	4,106.6			3,692.7
Cash	168.4			136.3
Reinsurance recoverable on paid and unpaid losses	552.9			484.2
Insurance and reinsurance premiums receivable	789.0			730.1
Funds held by ceding companies	244.1			293.9
Ceded unearned insurance and reinsurance premiums	172.5			162.0
Deferred acquisition costs	145.2			148.2
Float assets	2,072.1			1,954.7
Insurance float	$	2,034.5		$	1,738.0
Insurance float as a multiple of total capital(1)	0.9		x	0.7		x
Insurance float as a multiple of Sirius Group's common shareholders' equity	1.4		x	1.1		x

(1)See calculation of total capital in the table below under "Financing."

Financing

Sirius Group can provide no assurance that, if needed, it would be able to obtain additional debt or equity financing on satisfactory terms, if at all. In particular, as discussed in Item 1A, "Risk Factors," in our 2019 Annual Report, the CMB Resolution (as defined therein) may prohibit our Board of Directors from issuing any common or preference shares, warrants, options or other forms of share equity, or to confer any new share rights or implement any rights plan, or to amend or vary or alter any rights attaching to any existing shares, in each case without the prior approval of holders of the common shares of the Company representing at least 75% of the shareholder voting rights. The approval of holders of the common shares of the Company representing at least 75% of the shareholder voting rights cannot be assured. As such, the CMB Resolution may prevent Sirius Group from performing a number of matters necessary to the operation of its business, including raising capital, even if necessary to meet regulatory or rating agency capital requirements, to finance its operations or to increase its public float, as well as incentivizing employees using shares of the Company, and completing equity-based financing of transactions without the prior approval of holders of the common shares of the Company representing at least 75% of the shareholder voting rights.

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The following table summarizes Sirius Group's capital structure as of September 30, 2020 and December 31, 2019:

(Expressed in millions of U.S. dollars, except ratios)	September 30, 2020			December 31, 2019
2017 SEK Subordinated Notes	$	301.3		$	291.2
2016 SIG Senior Notes	394.5			394.0
Total debt	695.8			685.2
Series B preference shares	197.5			223.0
Common shareholders' equity	1,459.2			1,640.4
Total capital	$	2,352.5		$	2,548.6
Total debt to total capital	30		%	27		%
Total debt and Series B preference shares to total capital	38		%	36		%

2017 SEK Subordinated Notes

On September 22, 2017, Sirius Group issued floating rate callable subordinated notes denominated in SEK in the amount of SEK 2,750 million (or $346 million on date of issuance) at a 100% issue price ("2017 SEK Subordinated Notes"). The 2017 SEK Subordinated Notes were issued in an offering that was exempt from the registration requirements of the Securities Act of 1933 (the "Securities Act"). The 2017 SEK Subordinated Notes bear interest on their principal amount at a floating rate equal to the applicable Stockholm Interbank Offered Rate ("STIBOR") for the relevant interest period plus an applicable margin, payable quarterly in arrears on March 22, June 22, September 22, and December 22 in each year commencing on December 22, 2017, until maturity in September 2047.

See Note 10 "Debt and standby letters of credit facilities" and Note 14 "Common shareholder's equity, mezzanine equity, and non-controlling interests" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q for further details and discussion with respect to the 2017 SEK Subordinated Notes.

2016 SIG Senior Notes

On November 1, 2016, Sirius Group issued $400 million face value of senior unsecured notes ("2016 SIG Senior Notes") at an issue price of 99.209% for net proceeds of $392 million after taking into effect both deferrable and non-deferrable issuance costs. The 2016 SIG Senior Notes were issued in an offering that was exempt from the registration requirements of the Securities Act. The 2016 SIG Senior Notes bear an annual interest rate of 4.6%, payable semi-annually in arrears on May 1, and November 1, in each year commencing on May 1, 2017, until maturity in November 2026.

See Note 10 "Debt and standby letters of credit facilities" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q for further details and discussion with respect to the 2016 SIG Senior Notes.

Series B Preference Shares

In connection with the closing of the merger of Sirius Group with Easterly Acquisition Corp. (the “Easterly Merger”) on November 5, 2018, Sirius Group issued 11,901,670 of the 15,000,000 authorized Series B preference shares, with a par value of $0.01 per share, to affiliated funds of Gallatin Point Capital, The Carlyle Group, Centerbridge Partners, L.P. and Bain Capital Credit (collectively, the "Preference Share Investors") as part of the private placement of Series B preference shares, common shares, and warrants in connection with the Easterly Merger. The Series B preference shares contain both a mandatory conversion and optional redemption features, with the optional redemption features allowing for settlement in either common shares or cash. Sirius Group accounts for the Series B preference shares outside of permanent equity as mezzanine equity in the Consolidated Balance Sheets as its ability to settle in common shares cannot be assured, and thus we presume that Sirius Group will be required to settle the Series B preference shares in cash, as if it were a redemption feature.

The Series B preference shares rank senior to common shares with respect to dividend rights, rights of liquidation, winding-up, or dissolution of the Company and junior to all of the Company's existing and future policyholder obligations and debt obligations. Without the consent of the holders of the Series B preference shares, the Company may not issue any class or series of shares that rank senior or pari passu with the Series B preference shares as to the payment of dividends or as to distribution of assets upon any voluntary or involuntary liquidation, winding-up or dissolution of the Company, if the aggregate gross proceeds from the issuance of all such senior or pari passu shares equals or exceeds $100 million.

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The Company adjusts the carrying value of the Series B preference shares to equal the redemption value at the end of each reporting period. As of September 30, 2020 and December 31, 2019, the balance of the Series B preference shares was $198 million and $223 million, respectively.

In April and May 2020, the Company received letters from the Preference Share Investors, including Notices of Redemption claiming that there has been a change in control of Sirius Group within the meaning of the Certificate of Designation of the Series B preference shares and demanding the redemption of all of their Series B preference shares. The Company has reviewed the Notices of Redemption and related attachments, and continued its inquiry into the matters asserted therein. In connection with that inquiry, the Company received a letter from CMIG International confirming that (i) CMIG International continues to own 100% of the outstanding equity of CM Bermuda, and there have been no transfers of any shares of CM Bermuda (or CMIG International) and (ii) there have been no transfers of the shares owned by CM Bermuda, in each case since the initial listing of the Company’s common shares in November 2018. In addition, the Company received a secretary’s certificate from CM Bermuda identifying CMIG International as CM Bermuda’s sole shareholder. CM Bermuda also provided a letter from its lead facility agent confirming on behalf of the lenders under CM Bermuda’s facility agreement that no default or event of default has been declared under the facility agreement and that the facility agent has not exercised any of the rights that may be available it under an event of default. The letter further confirms that at no time has any lender or any trustee appointed on behalf of a lender acquired direct or indirect beneficial ownership of any of the shares of Sirius Group, CM Bermuda, CMIG International or China Minsheng Investment Group Corp., Ltd. As a result of such inquiry, Sirius Group responded to the Preference Share Investors that it is not aware of any facts that would support the conclusion that an event has occurred that would result in a change in beneficial ownership of the shares of the Company owned by CM Bermuda that would give rise to a redemption right by the Preference Share Investors. As such, Sirius Group concluded and notified the Preference Share Investors that they are not entitled at this time to elect a redemption of any of their Series B preference shares.

On September 4, 2020, TPRE entered into a transaction agreement (the “Transaction Agreement”) by and among TPRE and the Preference Share Investors. Pursuant to the terms of the Transaction Agreement, the Preference Share Investors will exchange their existing Series B preference shares of Sirius Group for new Series B preference shares, par value $0.10, of TPRE (the “SiriusPoint Preference Shares”) upon consummation of the proposed Merger (“Closing”), pursuant to the Merger Agreement. In exchange for the SiriusPoint Preference Shares, the Preference Share Investors have also agreed to toll certain potential claims they may have against Sirius Group from the date of the Transaction Agreement until Closing or the earlier termination of the Transaction Agreement, and have agreed to release such potential claims upon Closing.

Standby letter of credit facilities

On November 6, 2019, Sirius International agreed to renew two standby letter of credit facility agreements totaling $125 million to provide capital support for Lloyd's Syndicate 1945. The first letter of credit is a $90 million facility with Nordea Bank Abp, London Branch, which is issued on an unsecured basis. The second letter of credit is a $35 million facility with DNB Bank ASA, Sweden Branch, $25 million of which is issued on an unsecured basis. Each facility is renewable annually. The above referenced facilities are subject to various affirmative, negative and financial covenants that the Company considers to be customary for such borrowings, including certain minimum net worth and maximum debt to capitalization standards.

Sirius International has other secured letter of credit and trust arrangements with various financial institutions to support its insurance operations. As of September 30, 2020 and December 31, 2019, these secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust of SEK 4.4 billion and SEK 3.4 billion, respectively, or $488 million and $363 million, respectively (based on the September 30, 2020 and December 31, 2019 SEK to USD exchange rates). As of September 30, 2020 and December 31, 2019, Sirius America Insurance Company's trust arrangements were collateralized by pledged assets and assets in trust of $48 million and $58 million, respectively. As of September 30, 2020 and December 31, 2019, Sirius Bermuda's letters of credit and trust arrangements were collateralized by pledged assets and assets in trust of $520 million and $784 million, respectively.

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Revolving credit facility

In February 2018, Sirius Group, through its indirectly wholly-owned subsidiary SIG entered into a three-year, $300 million senior unsecured revolving credit facility (the "Facility"). The Facility provides access to loans for working capital and general corporate purposes, and letters of credit to support obligations under insurance and reinsurance agreements and retrocessional agreements. The Facility is subject to various affirmative, negative and financial covenants that Sirius Group considers to be customary for such borrowings, including certain minimum net worth, maximum debt to capitalization and financial strength rating standards. As of September 30, 2020, there were no outstanding borrowings under the Facility.

Debt and standby letter of credit facility covenants

As of September 30, 2020, Sirius Group was in compliance with all of the covenants under the 2017 SEK Subordinated Notes, the 2016 SIG Senior Notes, the Nordea Bank Abp, London Branch facility, and the DNB Bank ASA, Sweden Branch facility. In addition, as of September 30, 2020, Sirius Group was in compliance with all of the covenants under the Facility.

Off Balance Sheet Arrangements

Sirius Group is not party to any off-balance sheet transaction, agreement or other contractual arrangement as defined by Item 303(a)(4) of Regulation S-K to which an entity unconsolidated with Sirius Group is a party that management believes is reasonably likely to have a current or future effect on its financial condition, revenues or expenses, results of operations, liquidity, capital expenditures or capital resources that Sirius Group believes is material to investors.

Contractual Obligations and Commitments

In the normal course of business, we are party to a variety of contractual obligations, summarized as of December 31, 2019 in our 2019 Annual Report. We consider these contractual obligations when assessing our liquidity requirements. During the nine months ended September 30, 2020, other than as disclosed in Note 5 "Reserves for unpaid losses and loss adjustment expenses" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q with respect to an increase in our reserve for loss and LAE reserves, and Note 10 "Debt and standby letters of credit facilities" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q with respect to our long term debt obligations, there were no other material changes in our contractual obligations as disclosed in the table of contractual obligations, and related footnotes, included in our 2019 Annual Report.

Cash Flows

Sirius Group derives cash primarily from the net inflow of premiums less claim payments related to underwriting activities, from fee income, and from net investment income. The insurance and reinsurance business inherently provides liquidity, as premiums are received in advance of the time claims are paid. However, the amount of cash required to fund claim payments can fluctuate significantly from period to period, due to the low frequency and high severity nature of certain types of business we write. Sirius Group's remaining cash flows are generally reinvested in our investment portfolio. In addition, as previously disclosed, Sirius Group has access to the $300 million Facility that provides access to loans for working capital and general corporate purposes, and letters of credit to support obligations under insurance and reinsurance agreements and retrocessional agreements.

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The following table summarizes our consolidated cash flows from operating, investing, and financing activities for the nine months ended September 30, 2020 and 2019.

	Nine months ended
(Millions)	September 30, 2020		September 30, 2019
Net cash provided from (used for)(1)
Operations	$	115.5	$	87.9
Investing activities	(58.6)		(50.8)
Financing activities	(29.4)		(0.1)
Effect of exchange rate changes on cash	6.1		(9.4)
Increase in cash during year	$	33.6	$	27.6

(1)Refer to Consolidated Statements of Cash Flows included in Sirius Group's Unaudited Consolidated Financial Statements included in "Part I, Item 1. Financial Statements."

Cash flows from operations for the nine months ended September 30, 2020 and 2019

Net cash provided from operations was $116 million and $88 million for the nine months ended September 30, 2020 and 2019, respectively. Cash flows from operations increased $28 million for the nine months ended September 30, 2020 compared to the nine months ended September 30, 2019 due to higher amounts of net premiums collected which were partially offset by higher net paid losses, lower net service fee income, and lower net investment income.

Long-term compensation items affecting cash flows from operations

For each of the nine months ended September 30, 2020 and 2019, Sirius Group made long-term incentive payments totaling $2 million.

For the nine months ended September 30, 2020, Sirius Group made retention related award payments totaling $7 million that were issued to key employees in November 2019. See Note 13 "Share-based compensation" in Sirius Group's unaudited financial statements included elsewhere in this Quarterly Report on Form 10-Q for further details and discussion.

Cash flows (used for) investing and financing activities for the nine months ended September 30, 2020 and 2019

Cash flows (used for) investing activities were $(59) million and $(51) million for the nine months ended September 30, 2020 and 2019, respectively.

Cash flows (used for) financing activities were $(29) million for the nine months ended September 30, 2020 and insignificant for the nine months ended September 30, 2019.

Financing and other capital activities

On September 24, 2020, Sirius Group paid $4 million to WE B CEJS (formerly known as Armada Enterprises LLC) as a contingent consideration payment for the three-year contingent earn-out mechanism from the Armada Earnout for performance related to the 2019 underwriting year. Previously, on April 17, 2020, Sirius Group paid $6 million to WE B CEJS as a contingent consideration payment for performance related to the 2017 and 2018 underwriting years. See Note 3 "Significant transactions" in Sirius Group's audited financial statements included in our 2019 Annual Report for further details and discussion with respect to the Armada Earnout.

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On July 2, 2020, Sirius Group paid $18 million to IMGAH for the contingent consideration payment for the 2019 calendar year, which represents the final contingent consideration payment. See Note 3 "Significant transactions" in Sirius Group's audited financial statements included in our 2019 Annual Report for further details and discussion with respect to the IMGAH contingent consideration.

During the nine months ended September 30, 2020, Sirius Group paid $9 million of interest on the 2016 Senior Notes and $9 million of interest on the 2017 SEK Subordinated Notes.

During the nine months ended September 30, 2019, Sirius Group paid $9 million of interest on the 2016 Senior Notes and $9 million of interest on the 2017 SEK Subordinated Notes.

Summary of Critical Accounting Estimates

Our Consolidated Financial Statements include certain amounts that are inherently uncertain and judgmental in nature. As a result, we are required to make assumptions and best estimates in order to determine the reported values. We consider an accounting estimate to be critical if: (1) it requires that significant assumptions be made in order to deal with uncertainties and (2) changes in the estimate could have a material impact on our results of operations, financial condition or liquidity.

As disclosed in our 2019 Annual Report, we believe that the material items requiring such subjective and complex estimates are our:

Loss and LAE Reserves

Fair Value Measurements

Goodwill

Premiums

Income Taxes

There have been no material changes to the Company's critical accounting estimates for the nine months ended September 30, 2020. For additional information regarding our critical accounting estimates, refer to our 2019 Annual Report.

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ITEM 3. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK

Sirius Group's consolidated balance sheet includes a substantial amount of assets and liabilities whose fair values are subject to market risk. The term "market risk" refers to the risk of loss arising from adverse changes in interest rates, credit spreads, equity markets prices and other relevant market rates and prices. Due to Sirius Group's sizable investment portfolio, market risk can have a significant effect on Sirius Group's consolidated financial position.

See Part II, Item 1A, "Risk Factors," for changes in Sirius Group's market risk due to the COVID-19 pandemic.

ITEM 4. CONTROLS AND PROCEDURES

Evaluation of Disclosure Controls and Procedures

We maintain disclosure controls and procedures that are designed to ensure that information required to be disclosed in our reports filed pursuant to the Securities Exchange Act of 1934, as amended (the "Exchange Act"), is recorded, processed, summarized and reported within the time periods specified in the SEC's rules, regulations and related forms, and that such information is accumulated and communicated to our management, including our Chief Executive Officer and Chief Financial Officer, as appropriate, to allow timely decisions regarding required disclosure.

As required by Rules 13a-15(e) and 15d-15(e) under the Exchange Act, Sirius Group's management, with the participation of our Chief Executive Officer and Chief Financial Officer, carried out an evaluation of the effectiveness of our disclosure controls and procedures as of September 30, 2020. Based upon that evaluation, our Chief Executive Officer and Chief Financial Officer concluded that Sirius Group's disclosure controls and procedures are effective in allowing information required to be disclosed in reports filed under the Exchange Act to be recorded, processed, summarized and reported within time periods specified in the rules and forms of the SEC, and that such information is accumulated and communicated to Sirius Group's management, including our Chief Executive Officer and Chief Financial Officer, as appropriate to allow timely decisions regarding required disclosure.

Changes in Internal Control Over Financial Reporting

During the most recently completed fiscal quarter, there have been no changes in our internal control over financial reporting that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

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PART II. OTHER INFORMATION

ITEM 1. LEGAL PROCEEDINGS

Sirius Group, and the insurance and reinsurance industry in general, are routinely subject to claims-related litigation and arbitration in the normal course of business, as well as litigation and arbitration that do not arise from, or are not directly related to, claims activity. Sirius Group estimates of the costs of settling matters routinely encountered in claims activity are reflected in the reserves for unpaid loss and LAE.

We are not a party to any material legal proceedings arising outside the ordinary course of business.

ITEM 1A. RISK FACTORS

We face a variety of risks and uncertainties that are inherent in our business and our industry, including operational, industry and regulatory risks. Such risks and uncertainties could cause our actual results to differ materially from our forward-looking statements, expectations and historical trends. As of the date of this report, there have been no material changes to the risk factors disclosed in Item 1A. "Risk Factors" in our 2019 Annual Report, except as set forth below.

Risks Related to COVID-19

The novel coronavirus (COVID-19) pandemic has adversely affected our business. Epidemics, pandemics, and other public health threats, including the ongoing COVID-19 pandemic, could have a material adverse effect on Sirius Group’s business, including our results of operations, financial position and/or liquidity, in a manner and to a degree that cannot be predicted.

In December 2019, the novel coronavirus (COVID-19) was reported in Wuhan, China, and the World Health Organization declared it a global health emergency on January 30, 2020. Since January 2020, the Company has been monitoring the impact of COVID-19 on Sirius Group's business. Beginning in March 2020, COVID-19 began to impact the global economy and the results of our operations. Because of the size and duration of this pandemic, all of the direct and indirect consequences of COVID-19 are not yet known and may not emerge for some time. The future impact of the pandemic on us is highly uncertain and cannot be predicted, but it could have a material adverse impact on the future results of operations, financial position and/or liquidity of Sirius Group. The extent of the impact, if any, will depend on future developments, including actions taken to contain COVID-19 and the uncertain impact of potential judicial, legislative and regulatory actions by local, state and national governmental and regulatory bodies. Risks presented by the ongoing effects of COVID-19 include the following:

•Gross Written Premiums. COVID-19 has had a negative impact on general economic activity will which has, in turn, negatively impacted our premium volumes. The degree of the continued impact will depend on the extent and duration of the economic contraction. As a result of the anticipated impact of the pandemic on our earned premiums, we may experience an increase in our underwriting expense ratio. Sirius Group has experienced and may continue to experience lower gross written premiums for travel medical and trip cancellation insurance.

•Increased Risk of Loss. Sirius Group has experienced and may continue to experience an increased risk of loss in certain lines of business, including contingency, accident and health, workers ' compensation, trade credit, casualty and its property (re)insurance due to business interruption and global supply chains disruptions. For example, Sirius Group previously reported that we recorded $192 million of estimated ultimate losses in our underwriting losses related to the COVID-19 pandemic. During the third quarter of 2020, we reviewed our inforce (re)insurance portfolios to reevaluate our estimate of ultimate losses from the COVID-19 pandemic, and as a result of new information and more detailed modeling, we increased our estimates by $39 million, which included $31 million of losses from Global A&H primarily from contracts covering infectious disease related expenses. Sirius Group has currently recorded losses of $72 million in its other property and property catastrophe excess reinsurance lines of business due to business interruption, and has experienced losses of $47 million pertaining to actual and projected canceled or postponed major events. Sirius Group may also experience elevated frequency and severity in its workers’ compensation lines related to compensable claims by workers who have suffered from injury or illness in the course of their employment. Sirius Group has experienced and may continue to experience risk of loss in its casualty business, including professional liability treaties that cover health care, hospitals, long term care providers and directors and officers. Sirius Group has experienced and may continue to experience losses resulting from mortality, increased medical expenses, and trip cancellation in its accident and health portfolio. The economic volatility may also lead to increased losses within the trade credit portfolio, and there may be additional future losses from COVID-19 which have not yet been reflected in Sirius Group’s estimates, if loss emergence varies from our current expectations. For further discussion of the risks and exposure related to unpredictable catastrophic events, see “Sirius Group is exposed to unpredictable catastrophic

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events that could adversely affect its results of operations and financial condition” included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

•Estimated Loss Reserves. The anticipated and unknown risks related to COVID-19 may cause additional uncertainty in the estimation of claim and claim adjustment expense reserves. For example, the behavior of claimants and policyholders may change in unexpected ways. The disruption to court systems may have an impact on the timing and amounts of claims settlements; and the actions taken by governmental bodies, both legislative and regulatory, in reaction to COVID-19 and their related impacts are difficult to predict. As a result, our estimated level of claims and claim adjustment expense reserves may change.

•Investments. During the first quarter of 2020, Sirius Group experienced losses in its investment portfolio as a result of volatile markets, such as a decline in interest rates, a sharp decline in equity markets and a widening of credit risk spreads for bonds. In addition, the disruption in the financial markets caused by COVID-19 contributed to net unrealized investment losses, primarily due to the impact of changes in fair value on our equity investments and, to a lesser extent, change in unrealized losses in our fixed-income investment portfolio. While our investment portfolio improved during the second and third quarters of 2020, there is no guarantee that the losses experienced during the first quarter 2020 will not occur again. Our corporate fixed income portfolio may also be adversely impacted by ratings downgrades, increased bankruptcies and credit spread widening in distressed industries, such as energy, gaming, lodging and leisure, autos, airlines and retail. In addition, in recent years, many state and local governments have been operating under deficits or projected deficits. These deficits may be exacerbated by the costs of responding to COVID-19 and reduced tax revenues due to adverse economic conditions. Our investment portfolio also includes residential mortgage-backed securities, commercial mortgage-backed securities and wholly-owned real estate, all of which could be adversely impacted by declines in real estate valuations and/or financial market disruption, including a heightened default risk on the underlying mortgages and on rent receivables. Further disruptions in global financial markets due to the continuing impact of COVID-19 could result in additional net realized investment losses, including potential impairments in our fixed income portfolio. Further disruptions in global financial markets could adversely impact our net investment income in future periods from our non-fixed income investment portfolio. For further discussion of the risks related to our investment portfolio, see “Sirius Group’s investment portfolio may suffer reduced returns or losses, which could adversely affect Sirius Group’s results of operations and financial condition. Adverse changes in interest rates, foreign currency exchange rates, equity markets, debt markets or market volatility could result in significant losses to the fair value of Sirius Group’s investment portfolio” and “Unexpected volatility or illiquidity associated with some of Sirius Group’s investments could significantly and negatively affect Sirius Group’s financial results, liquidity and ability to conduct business” included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

•Inflation. It is possible that changes in economic conditions and steps taken by the federal government and the Federal Reserve in response to COVID-19 could lead to higher inflation than we had anticipated, which could in turn lead to an increase in our loss costs and the need to strengthen claims and claim adjustment expense reserves. These impacts of inflation on loss costs and claims and claim adjustment expense reserves could be more pronounced for those lines of business that require a relatively longer period of time to finalize and settle claims for a given year and, therefore more inflation sensitive. Inflation could also adversely impact our general and administrative expenses. Changes in interest rates caused by inflation affect the carrying value of our fixed maturity investments and returns on our fixed maturity and short-term investments. An increase in interest rates reduces the market value of existing fixed maturity investments, thereby negatively impacting our book value.

•Foreign Currency Exchange Rate Changes. As a result of our business outside of the United States, primarily in Europe, Japan, and the United Kingdom (including Lloyd’s), our shareholders' equity is also subject to the effects of changes in foreign currency exchange rates. Movement of the U.S. dollar compared to other currencies could result in a further reduction of shareholders’ equity.

•Further Ratings Downgrades. Third-party rating agencies assess and rate the financial strength, including claims-paying ability, of insurers and reinsurers. These ratings are based upon criteria established by the rating agencies and are subject to revision at any time at the sole discretion of the agencies. Rating agencies periodically evaluate Sirius Group to confirm that it continues to meet the criteria of the ratings previously assigned to Sirius Group. If the rating agencies determine that Sirius Group's operating performance has further deteriorated as a result of the COVID-19 pandemic, they could downgrade or withdraw Sirius Group's financial strength ratings which could have a material adverse effect on our results of operations, financial position and/or liquidity. For additional discussion on how a ratings downgrade can impact Sirius Group, see "Sirius Group is reliant on financial strength and creditworthiness ratings, and any downgrade or withdrawal of ratings and/or change in outlook may have a material adverse effect on

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Sirius Group's business, prospects, financial condition and results from operations" included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

•Counterparty Credit Risk and Retrocessional Arrangements. A prolonged economic downturn due to the COVID-19 pandemic would increase our credit risk, reflecting our counterparty dealings with agents, brokers, customers and retrocessionaires. Certain of our policyholders and intermediaries, including reinsurance and retrocession counterparties, may not pay amounts owed to us due to insolvency or other reasons. Insolvency, liquidity problems, distressed financial condition due to the impact of the COVID-19 pandemic or the general effects of economic recession may increase the risk that policyholders or intermediaries, such as insurance brokers, may not pay a part of or the full amount of premiums owed to us, despite an obligation to do so. The terms of our contracts, or actions by our regulators, may not permit us to cancel our policies even though we have not received payment. We may further decide (or be obliged by regulation) to refund premiums already paid where it is judged that the COVID-19 pandemic has reduced the customer need for coverage. The COVID-19 pandemic could impact our ability to obtain reinsurance and retrocessional arrangements on favorable terms which could limit the amount of business we are willing to write or reduce our reinsurance protection for large loss events.  For a further discussion, see “Sirius Group’s reliance on intermediaries subjects it to the intermediaries’ credit risk” included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

•Potential Adverse Judicial, Legislative and/or Regulatory Action. Like many reinsurers and insurers, we have exposure to losses from COVID-19-related claims, primarily in our property and contingency business. Whether the COVID-19 pandemic triggers coverage is dependent on specific policy language, terms and exclusions. However, certain domestic and international governmental authorities and regulatory bodies have proposed to take actions to address and contain the impact of the COVID-19 pandemic that may adversely affect Sirius Group. For example, we are subject to government and/or regulatory action that may seek to retroactively mandate coverage for losses which our (re)insurance policies were not designed or priced to cover. Currently, in some countries there is proposed legislation, governmental actions and courts cases that may require (re)insurers to cover business interruption claims irrespective of terms, exclusions or other conditions included in the policies that would otherwise preclude coverage. Should such proposed regulations, legislation, governmental actions or court cases be implemented, our (re)insurance contracts may be interpreted to provide coverage for these business interruption losses, notwithstanding the fact that such losses fall outside of the terms and conditions of the underlying contracts. These and other future judicial, legislative or regulatory actions could have a material adverse impact on our results of operations, financial position and/ or liquidity and make it difficult to predict the total amount of losses we could incur as a result of the COVID-19 pandemic. In addition, a number of states in the United States have instituted, and others are considering instituting, changes designed to effectively expand workers' compensation coverage by creating presumptions of compensability of claims for certain types of workers. Regulatory restrictions or requirements could also impact pricing, risk selection and our rights and obligations with respect to our policies and insureds, including Sirius Group’s ability to cancel policies or Sirius Group’s right to collect premiums. Recently, in Germany, the "Bavarian Solution" has gained wide spread acceptance and the U.K.'s Financial Conduct Authority is litigating a number of tests cases addressing business interruption claims against insurance companies. The "Bavarian Solution" proposes that the state carry 70% of business interruption losses and the remaining 30% of losses are proposed to be split between an insured and its insurance company. Following payments of business interruption losses to its insureds, insurance companies are expected to seek cover from the reinsurance market. In the United States, at least one state regulator has issued an order requiring insurers to issue premium refunds, and regulators in other states could take similar actions.

•Operational Disruptions and Heightened Cybersecurity Risks. Sirius Group’s operations could be disrupted if key members of our senior management or a significant percentage of our workforce or the workforce of our agents, brokers, suppliers or third party providers are unable to continue to work because of illness, death, government directives or otherwise. Further, limitation on travel and social distancing requirements implemented in response to the COVID-19 pandemic may challenge our ability to maintain our business relationships with our current clients and develop new client relationships and business which may impact our ability to write new insurance or reinsurance business and market our products and services as anticipated prior to the COVID-19 pandemic. In addition, the interruption of our, or third party, system capabilities could result in a deterioration of our ability to write and process new and renewal business, provide customer service, pay claims in a timely manner or perform other necessary business functions. Having shifted to remote working arrangements, we also face a heightened risk of cybersecurity attacks or data security incidents and are more dependent on internet and telecommunications access and capabilities. An extended period of remote work arrangements could strain our business continuity plans and could negatively affect our internal control over financial reporting as most of our employees are required to work from home. As a result, new processes, procedures and controls could be and have been required to respond to changes in our business environment. For a further discussion, see “Sirius Group may be unable to adequately maintain its systems and

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safeguard the security of the data it holds or the data held by its business partners and service providers, which may adversely impact Sirius Group’s ability to operate its business and cause reputational harm and financial loss” included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

•Reputational Damage. We could experience reputational damage resulting from potential claims disputes and underwriting renewal actions that we may take in connection with the management of potential COVID-19 pandemic losses.

Due to the evolving and uncertain nature of the COVID-19 pandemic, we cannot estimate its ultimate impact at this time. Depending on the scope and duration of the COVID-19 pandemic, the events described above may have a material adverse effect on our results of operations, financial position and/ or liquidity. Moreover, the potential effects of the COVID-19 pandemic could exacerbate the impacts of many other risk factors that we identify in the Company's 2019 Annual Report, including, but not limited to, risks that can impact Sirius Group as a result of an economic downturn; potential litigation claims brought against the Company; further losses from event cancellations in our contingency portfolio and other coverages from our reinsurance and insurance contracts; negative impact to revenues and earnings; and impairment of goodwill and intangible assets and potential valuation allowances on deferred tax assets. Since the COVID-19 pandemic is continuously evolving, the potential impacts to the risks related to our business that are further described in the Company's 2019 Annual Report remain uncertain and new and potentially unforeseen risks beyond those described above and in the Company's 2019 Annual Report may arise. Even after the COVID-19 pandemic subsides, the U.S. and world economies may experience a prolonged economic recession, in which event our results of operations, financial position and/ or liquidity may be materially and adversely affected.

Risks Related to the Merger

Completion of the Merger is subject to the satisfaction or waiver of the conditions precedent to the consummation of the proposed Transactions involving the Company, TPRE and Merger Sub, including, without limitation, the receipt of shareholder and regulatory approvals (including approvals, authorizations and clearance by antitrust authorities and insurance regulators necessary to complete such proposed merger transaction) which may not be received on the terms desired or anticipated (and the risk that such approvals may result in the imposition of conditions that could adversely affect the combined company or the expected benefits of such proposed merger transaction).

The consummation of the Merger is subject to the satisfaction or waiver of certain conditions, including, among others, (i) the affirmative vote in favor of the approval of the Merger Agreement, the Merger and the Statutory Merger Agreement by the holders of a majority of the voting power of the Company Shares and the Company’s Series B preference shares, voting together as a single class, that are present (in person or by proxy) at the Company shareholder meeting called for such purpose, (ii) the affirmative vote in favor of the approval of the issuance of TPRE Shares in the Merger as contemplated by the Merger Agreement (the “TPRE Share Issuance”) by the holders of at least a majority of the voting power of TPRE Shares that are present (in person or by proxy) at the TPRE shareholder meeting called for such purpose, (iii) the expiration or termination of any applicable waiting period (together with any extensions thereof) under the Hart-Scott-Rodino Antitrust Improvements Act of 1976 and any other applicable antitrust laws, (iv) the receipt of certain approvals under applicable insurance laws, (v) the absence of any effective order issued by any governmental authority or court of competent jurisdiction or other legal restraint prohibiting or preventing the consummation of the Merger, (vi) in the case of each party’s obligation to effect the Merger, the absence of a material adverse effect with respect to the other party and its subsidiaries, taken as a whole, since the date of the Merger Agreement, (vii) in the case of each party’s obligation to effect the Merger, subject to certain materiality exceptions, the accuracy of the representations and warranties made by the other party, and compliance by the other party in all material respects with such party’s respective obligations under the Merger Agreement and (viii) other customary closing conditions.

Although each party has agreed to use respective efforts to obtain the requisite regulatory approvals, there can be no assurance that these approvals will be obtained and that the other conditions to completing the Merger will be satisfied. In addition, the governmental authorities from which the regulatory approvals are required may impose conditions on the completion of the Merger or require changes to the terms of the Merger or Merger Agreement. Such conditions or changes and the process of obtaining regulatory approvals could have the effect of delaying or impeding completion of the Merger or of imposing additional costs or limitations on the Company following completion of the Merger, any of which might have an adverse effect on the Company following completion of the Merger.

At the time of the execution and delivery of the Merger Agreement, CM Bermuda, which holds approximately 87% of the dispositive and voting power over the shares of the Company, entered into a Voting and Support Agreement pursuant to which CM Bermuda has agreed to vote or cause to be voted any of the Company Shares of which it is the beneficial or record owner in favor of the approval of the Merger, the other proposed Transactions, the Merger Agreement, the Statutory Merger Agreement, and any other matters necessary or reasonably requested by TPRE for consummation of the Merger and the other

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proposed Transactions. In addition, certain of TPRE’s directors and executive officers, including Mr. Daniel S. Loeb and certain entities affiliated with Mr. Loeb, entered into Voting and Support Agreements with the Company and TPRE pursuant to which such parties agreed to vote or cause to be voted any of the TPRE Shares of which such party is the beneficial or record owner in favor of the approval of the Merger, the other proposed Transactions, the Merger Agreement, the Statutory Merger Agreement, and any other matters necessary or reasonably requested by TPRE for consummation of the Merger and the Transactions. Accordingly, the Voting and Support Agreements make it more likely that the necessary shareholder approval will be received for the Merger but there is no guarantee that the Merger will be approved by a majority of the shareholders of TPRE. Failure to obtain TPRE shareholder approval for the Merger could negatively impact the price of our common shares, and as a result our results of operations, financial position and/ or liquidity may be materially and adversely affected.

Lawsuits relating to the Merger, the other proposed Transactions, circumstances arising prior to the announcement of the Merger or other matters could be filed against us and adversely impact our business, financial condition, operating results and share price and could delay, prevent or otherwise adversely impact the Merger Agreement or the combined company.

Litigation is common in connection with operation and acquisitions of public companies, regardless of any merits related to the claims. In the event lawsuits are filed against us related to the Merger, the other proposed Transactions or circumstances arising prior to the announcement of the Merger, the outcome of the lawsuits could be uncertain, and we may not be successful in defending against any such claims. Prior to the announcement of the Merger, Sirius Group received correspondence from shareholders, including the Series B preference shareholders, asserting various claims against the Board of Directors of the Company including, among other things, that the Board violated its fiduciary duties, and breached Sirius Group’s obligations pursuant to the Certificate of Designation and Shareholders Agreement. While the shareholders have not filed a lawsuit and have agreed to toll certain potential claims they may have against Sirius Group until the closing of the Merger (or earlier termination of the related tolling agreement), the shareholders have reserved their rights to pursue all available remedies, including without limitation, claims for breaches of the Certificate of Designation and the Shareholders Agreement, shareholder oppression, fraud and all other legal and equitable remedies and forms of relief under Bermuda, New York, Delaware and other applicable law. While we will defend against any such lawsuits, as appropriate, the costs of the defense of such actions and other effects of such litigation could have an adverse effect on our business, financial condition, operating results and trading price of the Company's common shares, and could ultimately delay, prevent or otherwise adversely impact the Merger or the combined company.

We could experience unanticipated negative reactions of rating agencies in response to the Merger and other proposed Transactions.

Third-party rating agencies assess and rate the financial strength, including claims-paying ability, of insurers and reinsurers. These ratings are based upon criteria established by the rating agencies and are subject to revision at any time at the sole discretion of the agencies. Rating agencies periodically evaluate Sirius Group to confirm that it continues to meet the criteria of the ratings previously assigned to Sirius Group. If the rating agencies determine that the Merger and other proposed Transactions will negatively impact the combined company's operating performance, they could downgrade or withdraw Sirius Group's financial strength ratings which could have a material adverse effect on our results of operations, financial position and/or liquidity. For additional discussion on how a ratings downgrade can impact Sirius Group, see "Sirius Group is reliant on financial strength and creditworthiness ratings, and any downgrade or withdrawal of ratings and/or change in outlook may have a material adverse effect on Sirius Group's business, prospects, financial condition and results from operations" included in Part I, Item 1A. "Risk Factors” in the Company’s 2019 Annual Report.

Unanticipated difficulties and expenses related to the Merger and other proposed Transactions could be significant and could have an adverse effect on our business, financial condition and operating results. In addition, termination of the Merger Agreement could negatively impact our financial condition and the share price of our common shares.

We have incurred and expect to continue to incur significant expenses in connection with the negotiation and completion of the Transactions. The substantial majority of non-recurring expenses will consist of transaction costs related to the Merger and include, among others, employee retention costs, fees paid to financial, legal and accounting advisors, severance and benefit costs and filing fees. If the Merger is not consummated, we may under certain circumstances be required to pay to TPRE a termination fee of approximately $50 million and/or reimburse TPRE for its incurred out-of-pocket expenses. The costs incurred in connection with the Transactions, other unanticipated costs and expenses, and/or the termination of the Merger Agreement, including a termination fee of $50 million, could adversely affect our business, financial condition, operating results and share price.

Uncertainties associated with the Merger may cause a loss of management and other key employees and disrupt our business relationships, which could adversely affect our business.

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Uncertainty about the effect of the Merger on our employees and our clients may have an adverse effect on our business. These uncertainties may impair our ability to attract, retain and motivate key personnel until the Merger is completed and for a period of time thereafter. Employee retention may be particularly challenging during the pendency of the Merger, as employees of the Company may experience uncertainty about their future roles with the combined company.  If key employees depart and as we face additional uncertainties relating to the Merger, our business relationships may be subject to disruption as brokers, insurers, cedants and other third parties attempt to negotiate changes in existing business relationships or consider entering into business relationships with parties other than the Company, TPRE or the combined company.  If key employees depart or if our existing business relationships suffer, our results of operations may be adversely affected. These effects may be exacerbated as a result of the announcement that our President & Chief Executive Officer and our Chief Strategy Officer & General Counsel will be stepping down from their respective roles as of the closing date of the Merger. The adverse effects of such disruptions could be further exacerbated by any delay in the completion of the Merger.

While the Merger is pending, we are subject to business uncertainties and contractual restrictions that could have an adverse effect on our business, financial condition and operating results.

The Merger Agreement includes restrictions on the conduct of our business prior to the completion or termination of the Merger, generally requiring us to conduct our business in the ordinary course and subjecting us to a variety of specified limitations absent TPRE's prior written consent. We may find that these and other contractual restrictions in the Merger Agreement may delay or prevent us from responding, or limit our ability to respond, effectively to competitive pressures, industry developments and future business opportunities that may arise during such period, even if our management believes they may be advisable. The pendency of the Merger may also divert management’s attention and our resources from ongoing business and operations. If any of these effects were to occur, it could have an adverse effect on our business, financial condition and operating results.

If our shareholders elect to receive the Share & CVR Election as merger consideration, the number of common shares of TPRE that such shareholders will receive in the Merger is based on a fixed exchange ratio. If our shareholders elect to receive the Mixed Election as merger consideration, the number of common shares and preference shares of TPRE that shareholders will receive in the Merger is based on an exchange ratio subject to a limited adjustment that may not fully reflect fluctuations in the value of TPRE's common shares. Because the market price of TPRE's common shares will fluctuate, our shareholders cannot be certain of the value of the portion of the merger consideration to be paid in TPRE common shares or preference shares.

Upon completion of the Merger, each issued and outstanding Company Share will be converted into the right to receive, at the election of the holder thereof, (i) the Cash Election, (ii) (A) 0.743 of TPRE Shares and (B) one CVR, which will represent the right to receive a contingent cash payment, and which, taken together with the fraction of the TPRE Share received, guarantee that on the second anniversary of the closing date of the Merger, the electing shareholder will have received equity and cash of at least $13.73 per share, or (iii) (A) $0.905 in cash, (B) a number of TPRE Shares equal to the Mixed Election Common Shares Exchange Ratio (as such term is defined in the Merger Agreement), (C) a number of newly issued TPRE Preference Shares equal to the Mixed Election Preference Shares Exchange Ratio (as such term is defined in the Merger Agreement), (D) 0.190 of a Warrant and (E) an Upside Right issued by TPRE.

The exchange ratio for determining the number of TPRE Shares our shareholders who elect to receive the Share & CVR Election will receive in the Merger is fixed and will not be adjusted for changes in the market price of TPRE Shares, which will likely fluctuate before and after the completion of the Merger. The exchange ratio for determining the number of TPRE Shares and TPRE Preference Shares our shareholders who elect to receive the Mixed Election will receive in the Merger will each be subject to a collar based on the volume weighted average price of TPRE Shares measured over the 15 trading days ending on the third trading day prior to the effective time of the Merger, but such adjustment may not fully reflect fluctuations in the value of the TPRE Shares before the completion of the Merger. Fluctuations in the value of TPRE Shares could result from changes in the business, operations or prospects of TPRE prior to or following the closing of the Merger, regulatory considerations, general market and economic conditions and other factors both within and beyond the control of us or TPRE. In addition, there is no guarantee that on the second anniversary of the closing date of the Merger that the contingent value right will deliver additional value to shareholders that make this election.

The Merger Agreement prohibits us from pursuing alternative transactions to the Merger and this prohibition prevents Sirius Group from affirmatively seeking offers from other possible acquirers that may be superior to the Merger. In addition, Sirius Group may not terminate the Merger Agreement without CMIG International and CM Bermuda's approval.

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The Merger Agreement prohibits the Company and our subsidiaries and to cause our directors, executive officers and employees from initiating, soliciting, knowingly encouraging, knowingly facilitating or entering into discussions or negotiations with any third party regarding alternative acquisition proposals. This provision prevents us from affirmatively seeking offers from other possible acquirers that may be superior to the pending Merger.

In addition, Sirius Group entered into the Transaction Matters Agreement pursuant to which, among other things and subject to the terms and conditions thereof, Sirius Group has agreed to pay for and reimburse CMIG International and CM Bermuda for certain legal and other advisory expenses incurred by CMIG International and CM Bermuda in connection with the Transactions and the related sales process or other discussions between CMIG International, CM Bermuda and Sirius Group occurring on or after March 6, 2020, and TPRE has agreed to assume such remaining payment obligations of the Company following the closing of the Merger. During the quarter ended September 30, 2020, the Company paid $2 million for certain legal expenses incurred by CM Bermuda and CMIG International in connection with the Transaction Matters Agreement. Under the terms of the Transaction Matters Agreement, Sirius Group is not permitted to terminate or threaten to terminate the Merger Agreement following a change by the TPRE board of directors of its recommendation to TPRE’s shareholders in favor of the TPRE Share Issuance without the prior written consent of CM Bermuda and CMIG International.

ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS

None.

ITEM 3. DEFAULTS UPON SENIOR SECURITIES

None.

ITEM 4. MINE SAFETY DISCLOSURES

Not applicable.

ITEM 5. OTHER INFORMATION

In the Current Report on Form 8-K filed by the Company on March 3, 2020, the Company announced that it expected to hold its 2020 Annual General Meeting of Shareholders (the "2020 Annual Meeting") on November 19, 2020. As the expected date of the 2020 Annual Meeting was more than 30 days after the anniversary of the Company's 2019 annual meeting, the Company announced that shareholder proposals submitted for inclusion in the proxy statement for the 2020 Annual Meeting must be received at the Company's principal executive offices no later than July 1, 2020 (which the Company determined to be a reasonable time before it expected to begin to print and send the proxy materials). The Company received no such shareholder proposals by the deadline. As disclosed in the Company's proxy statement filed on November 6, 2020, the 2020 Annual Meeting now will be held on December 29, 2020. The Company has determined not to extend the deadline for shareholders to submit a proposal for inclusion in the proxy statement.

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ITEM 6. EXHIBITS

3.1	Memorandum of Association of Sirius International Insurance Group, Ltd, as amended. (incorporated by reference to Exhibit 3.1 to the Annual Report on Form 10-K filed by Sirius International Insurance Group, Ltd. on March 14, 2019).
3.2	Bye-Laws of Sirius International Insurance Group, Ltd. (incorporated by reference to Exhibit 3.1 to the Current Report on Form 8-K filed by Sirius International Insurance Group, Ltd. on November 6, 2018).
3.3	Certificate of Designation of Series B Preference Shares of Sirius International Insurance Group, Ltd. (incorporated by reference to Exhibit 3.2 to the Current Report on Form 8-K filed by Sirius International Insurance Group, Ltd. on November 6, 2018).
10.9.1	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Restricted Share Unit Award, amending and restating the IPO Award granted on August 6, 2018.
10.9.2	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Restricted Share Unit Award, amending and restating the PSU Award granted on February 28, 2019.
10.9.3	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Restricted Share Unit Award, amending and restating the PSU Award granted on February 27, 2020.
10.9.4	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Special Restricted Share Unit Award Notice.
10.9.5	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Special Restricted Share Unit Award Notice.
10.9.6	Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan - Form of Special Restricted Share Unit Award Notice.
10.9.7	Letter Agreement, dated July 16, 2020, by and between Sirius International Insurance Group, Ltd. and Gene Boxer.
10.9.8	Letter Agreement, dated July 16, 2020, by and between Sirius International Insurance Group, Ltd. and Kernan V. Oberting.
31.1	Certification of Kernan "Kip" V. Oberting, Chief Executive Officer of Sirius International Insurance Group, Ltd., pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934.
31.2	Certification of Ralph Salamone, Chief Financial Officer of Sirius International Insurance Group, Ltd., pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934.
32.1	Certification of Kernan "Kip" V. Oberting, Chief Executive Officer of Sirius International Insurance Group, Ltd., pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
32.2	Certification of Ralph Salamone, Chief Financial Officer of Sirius International Insurance Group, Ltd., pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
99.1	Transaction Agreement, dated September 4, 2020, by and among Third Point Reinsurance Ltd., Bain Capital Special Situations Asia, L.P., CCOF Master, L.P., Centerbridge Credit Partners Master LP, and Centerbridge Special Credit Partners III, LP, and GPC Partners Investments (Canis) LP.
101.INS	Inline XBRL Instance Document
101.SCH	Inline XBRL Taxonomy Extension Schema Document
101.CAL	Inline XBRL Taxonomy Extension Calculation Linkbase Document
101.LAB	Inline XBRL Taxonomy Extension Label Linkbase Document
101.PRE	Inline XBRL Taxonomy Extension Presentation Linkbase Document
101.DEF	Inline XBRL Taxonomy Extension Definition Linkbase Document
104	Cover Page Interactive Data File (formatted as Inline XBRL and contained in Exhibit 101)

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SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

	SIRIUS INTERNATIONAL INSURANCE GROUP, LTD. (Registrant)
Date: November 9, 2020	By:	/s/ KERNAN "KIP" V. OBERTING
		Kernan "Kip" V. Oberting President and Chief Executive Officer (Principal Executive Officer)
Date: November 9, 2020	By:	/s/ RALPH A. SALAMONE
		Ralph A. Salamone Chief Financial Officer (Principal Financial Officer & Principal Accounting Officer)

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EX-10.9.1

Exhibit 10.9.1

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Restricted Share Unit Award Agreement (together with this Award Notice, the "Agreement”). The Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan. Please note that this Award and the Agreement is an amendment and restatement of a prior award of IPO Award granted to you on August 6, 2018.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest with respect to one-third of the aggregate number of Restricted Share Units on December 31, 2020 and with respect to two-thirds of the aggregate number of Restricted Share Units on December 31, 2021 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of December 31, 2021 that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your IPO Award, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:______________

Name:

Title:

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be settled in cash or publicly traded equity securities within 60 days following the termination of

employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    Good Reason. For purposes of this Award, “Good Reason” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define “Good Reason,” then “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; (ii) a diminution in the Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the Company; or (v) a material breach of any employment or other

material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award no earlier than January 1, 2022 but in no event later than March 15, 2022. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company.

5.Clawback of Proceeds.

5.1.    Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2.    Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2.     Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”) and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company: Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder: At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and

the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.2

Exhibit 10.9.2

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Restricted Share Unit Award Agreement (together with this Award Notice, the “Agreement”). The Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan. Please note that this Award and the Agreement is an amendment and restatement of a prior award of 2019 PSU granted to you on February 28, 2019.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest in full on December 31, 2021 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of the end of the calendar quarter immediately preceding the applicable Vesting Date that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your 2019 PSU, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:______________

Name:

Title:

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be settled in cash or publicly traded equity securities within 60 days following the termination of

employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    Good Reason. For purposes of this Award, “Good Reason” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define “Good Reason,” then “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; (ii) a diminution in the Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the Company; or (v) a material breach of any employment or other

material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award within 60 days after such shares become vested. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company.

5.Clawback of Proceeds.

5.1.    Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2.    Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2.     Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”) and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company: Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder: At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and

the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.3

Exhibit 10.9.3

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Restricted Share Unit Award Agreement (together with this Award Notice, the “Agreement”). The Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan. Please note that this Award and the Agreement is an amendment and restatement of a prior award of 2020 PSU granted to you on February 27, 2020.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest in full on December 31, 2022 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of the end of the calendar quarter immediately preceding the applicable Vesting Date that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your 2020 PSU, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:______________

Name:

Title:

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be settled in cash or publicly traded equity securities within 60 days following the termination of

employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    Good Reason. For purposes of this Award, “Good Reason” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define “Good Reason,” then “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; (ii) a diminution in the Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the Company; or (v) a material breach of any employment or other

material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award within 60 days after such shares become vested. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company.

5.Clawback of Proceeds.

5.1.    Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2.    Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2.     Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”) and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company: Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder: At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and

the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.4

Exhibit 10.9.4

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Special Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Special Restricted Share Unit Award Agreement (together with this Award Notice, the “Agreement”). The Special Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest with respect to one-third of the aggregate number of Restricted Share Units on December 31, 2021 and with respect to two-thirds of the aggregate number of Restricted Share Units on December 31, 2022 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Special Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of December 31, 2022 that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your IPO Award, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:    ________________

Name:

Title:    

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

SPECIAL RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be

settled in cash or publicly traded equity securities within 60 days following the termination of employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    For purposes of this Award, “Good Reason” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define “Good Reason,” then “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; (ii) a diminution in the Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the

Company; or (v) a material breach of any employment or other material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award no earlier than January 1, 2023 but in no event later than March 15, 2023. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company.

5.Clawback of Proceeds.

5.1. Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2. Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2. Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”) and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company:Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder:At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such

right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.5

Exhibit 10.9.5

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Special Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Special Restricted Share Unit Award Agreement (together with this Award Notice, the “Agreement”). The Special Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest in two equal installments on each of January 1, 2023 and January 1, 2024 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Special Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of the end of the calendar quarter immediately preceding the applicable Vesting Date that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your 2018 Performance Award, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:______________

Name:

Title:

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

2018 OMNIBUS INCENTIVE PLAN

SPECIAL RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be

settled in cash or publicly traded equity securities within 60 days following the termination of employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    Good Reason. For purposes of this Award, “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; provided, that, following a Change in Control, Good Reason shall not be deemed to have occurred under this clause (i) by reason of (1) a change in the Holder’s title in connection with the combination of the business of the Company and the business of an acquirer in connection with a Change in Control transaction (a “Combination”), (2) a change in the reporting responsibilities of the Holder (including both individuals who report to the Holder as well as individuals to whom the Holder report) in connection with a Combination, or (3) a change in the budget and budgeting responsibilities of the Holder or the Holder’s line of business in connection with a Combination, in each case so long as the day-to-day job responsibilities of the Holder after the closing of the Combination are substantially similar when measured against the day-to-day job responsibilities of the Holder before the closing of the Combination; (ii) a diminution in the

Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the Company; or (v) a material breach of any employment or other material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award within 60 days after such shares become vested. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company.

5.Clawback of Proceeds.

5.1.    Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2.    Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or

similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2.     Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”) and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of

any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company: Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder: At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.6

Exhibit 10.9.6

Sirius International Insurance Group, Ltd.

2018 Omnibus Incentive Plan

Special Restricted Share Unit Award Notice

Holder: [•]

You have been awarded Restricted Share Units (the “Award”) with respect to Common Shares of Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), pursuant to the terms and conditions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”) and the Special Restricted Share Unit Award Agreement (together with this Award Notice, the “Agreement”). The Special Restricted Share Unit Award Agreement and the Plan are attached hereto. Capitalized terms not defined herein shall have the meanings specified in the Plan.

This Agreement shall be null and void unless you agree to be bound by and accept this Agreement on or before July 31, 2020 by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley.

Grant Date:	July XX, 2020
Restricted Share Units:	You have been awarded a restricted share unit award with respect to [•] Common Shares (the “Restricted Share Units”), subject to adjustment as provided in the Plan.
Vesting Schedule:	Except as otherwise provided in the Plan, the Agreement or any other agreement between you and the Company or any of its Affiliates, the Restricted Share Units shall vest in full on December 31, 2022 (each such date, a “Vesting Date”), provided that you satisfy the employment vesting conditions set forth in the Special Restricted Share Unit Award Agreement.
Form of Settlement	The Award shall be settled in the form of a cash payment in an amount equal to the book value per share of the Common Shares, calculated as of the end of the calendar quarter immediately preceding the applicable Vesting Date that otherwise would be issued to you pursuant to Section 4 of the Agreement; provided, however, that in the event of a Change in Control pursuant to which the Award is substituted, assumed or continued by the surviving or acquiring corporation, or a parent corporation thereof, in accordance with Section 3.3(b) of the Agreement and Section 5.8 of the Plan, such substituted, assumed or continued award may be settled in common shares of acquiring or successor corporation or the ultimate parent corporation thereof, as determined by the Committee.

Acknowledgment of Cancellation You have been provided a separate disclosure regarding the cancellation of your 2019 PSU, the terms of which you have reviewed and consented to. You further acknowledge the Award is consideration for such cancellation and in full satisfaction thereof such that you have no outstanding or further rights with respect thereto. It is an express condition to your receipt of the Award that you acknowledge and agree to the terms set forth in the preceding sentences and, by accepting the Award, you do so acknowledge and agree.

Sirius International Insurance Group, Ltd.

By:______________

Name:

Title:

Acknowledgment, Acceptance and Agreement:

By accepting this grant, I hereby accept the Award and acknowledge and agree to be bound by the terms and conditions of this Award Notice, the Agreement and the Plan.

[•]

__________________________________Date [•]

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

2018 OMNIBUS INCENTIVE PLAN

SPECIAL RESTRICTED SHARE UNIT AWARD AGREEMENT

Sirius International Insurance Group, Ltd., a Bermuda exempted company (the “Company”), hereby grants to the individual (the “Holder”) named in the Award Notice attached hereto (the “Award Notice”) as of the grant date set forth in the Award Notice (the “Grant Date”), pursuant to the provisions of the Sirius International Insurance Group, Ltd. 2018 Omnibus Incentive Plan (the “Plan”), a Restricted Share Unit Award (the “Award”) with respect to the number of Common Shares set forth in the Award Notice, subject to the restrictions, terms and conditions set forth in the Plan and this agreement (this “Agreement”). Capitalized terms not defined herein shall have the meanings specified in the Award Notice or the Plan.

1.Award Subject to Acceptance of Agreement. The Award shall be null and void unless the Holder accepts this Agreement by clicking the accept radio button in the Company’s share administration tool, Shareworks by Morgan Stanley. In addition, the vesting provision of Section 3.2(b) – (c) and Section 3.3 hereof shall be subject to and conditioned on the Holder having executed previously and returned an original copy of the Restrictive Covenant Agreement previously provided to the Holder (the “Restrictive Covenant Agreement”).

2.Rights as a Shareholder. The Holder shall not be entitled to any privileges of ownership with respect to any Common Shares that are granted by this Award unless and until the Common Shares become vested pursuant to Section 3 and the Holder becomes the shareholder of record with respect to such Common Shares. As of each date on which the Company pays a cash dividend to record owners of Common Shares (a “Dividend Date”), the number of Common Shares subject to the Award shall increase by (i) the product of the total number of shares subject to the Award immediately prior to such Dividend Date multiplied by the dollar amount of the cash dividend paid per Common Share by the Company on such Dividend Date, divided by (ii) the Fair Market Value of a Common Share on such Dividend Date. Any such additional shares shall be subject to the same vesting conditions and payment terms set forth herein as the shares to which they relate.

3.Restriction Period and Vesting.

3.1. Service-Based Vesting Conditions. Subject to the remainder of this Section 3, the Award shall vest pursuant to the terms of this Agreement, the Plan and the Award Notice, provided that that the Holder remains in continuous employment with the Company during the period beginning on the Grant Date and ending on the applicable Vesting Date, each as set forth in the Award Notice (the “Restriction Period”). Notwithstanding the foregoing, the vesting provisions of Section 3.2(b) – (c) and Section 3.3. hereof shall lapse and any rights thereof shall be forfeited in its entirety if the Holder breaches any Restrictive Covenant Agreement then in effect prior to the date on which the Award is settled.

3.2. Termination of Employment.

(a)    Termination for any Reason if Holder has not Executed the Restrictive Covenant Agreement. If the Holder has not executed the Restrictive Covenant Agreement prior to the date

hereof, and the Holder’s employment with the Company is terminated prior to a Vesting Date by the Company or the Holder for any reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

(b)    Termination Without Cause, for Good Reason or Due to Death or Disability if Holder has executed the Restrictive Covenant Agreement. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, except as provided under Section 3.3, if the Holder’s employment with the Company is terminated prior to a Vesting Date (i) by the Company without Cause (including due to the Holder’s Disability), (ii) by the Holder for Good Reason or (iii) due to the Holder’s death, then any unvested portion of the Award shall become fully vested as of the date of such termination.

(c)    Termination for Cause or Voluntary Resignation. If the Holder’s employment with the Company is terminated prior to the end of the Restriction Period (i) by the Company for Cause or (ii) by the Holder for any reason other than Good Reason, then the unvested portion of the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.3. Change in Control. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, upon a Change in Control, the Committee, as constituted prior to the Change in Control, may treat this award in any manner authorized by the Plan, subject to the following:

(a)    Settlement of Award Not Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and not effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), the Award shall vest as of the date of the Change in Control. Any portion of the Award subject to this Section 3.3(a) shall be settled in cash within 60 days following the Change in Control.

(b)    Settlement of Award Properly Substituted or Assumed. In the event of a Change in Control pursuant to which the Award is outstanding and is effectively substituted, assumed or continued by the surviving or acquiring corporation in such Change in Control (as determined by the Board or Committee (as constituted prior to such Change in Control), with appropriate adjustments to the number and kind of shares, in each case, that preserve the value of the shares subject to the Award and other material terms and conditions of the outstanding Award as in effect immediately prior to the Change in Control), then any such substituted or continued Award shall provide that if the Company terminates the Holder’s employment without Cause (including due to Disability), the Holder resigns for Good Reason or the Holder’s employment terminates due to death, in any case, within 24 months following such Change in Control (and prior to a Vesting Date) and the Holder executes and does not revoke a waiver and release of claims in the form prescribed by the Company within 45 days after the date of such termination, the Award shall become fully vested as of the date of such termination. Any portion of the Award subject to this Section 3.3(b) shall be settled in cash or publicly traded equity securities within 60 days following the termination of employment. If, following a Change in Control, the Holder experiences a termination of employment prior to a Vesting Date other than as set forth in this Section 3.3(b), the Award shall be immediately forfeited by the Holder and cancelled by the Company.

3.4.    Definitions.

(a)    Cause. For purposes of this Award, “Cause” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define Cause, then Cause shall mean (i) a material and continued failure of the Holder to perform the Holder’s duties, other than due to death or Disability, which failure has continued for more than 30 days following written notice of such nonperformance from the Company; (ii) conviction of or pleading guilty or no contest to an act of fraud, embezzlement, or misappropriation of assets or property (tangible or intangible) of the Company or any Affiliate thereof; (iii) a material breach of the Restrictive Covenant Agreement; (iv) commission of a felony, including a plea of guilty or nolo contendere, or an indictment or written admission thereof; (v) gross negligence or willful misconduct in the performance by the Holder of his duties that is reasonably likely to have an adverse effect on the business or reputation of the Company or its Affiliates; or (vi) the Holder’s material violation of the material written policies of the Company (e.g., sexual harassment, data protection policy, etc.). For the avoidance of doubt, the definition of Cause as well as the consequences of termination for Cause as set out in the Plan, the Agreement and the Award Notice shall apply regardless of whether such termination of employment may be justified under any applicable employment protection legislation, and regardless of whether such termination may be challenged by the Holder, and regardless of whether such termination is invalidated by verdict or a court order.

(b)    Disability. For purposes of this Award, “Disability” shall mean, with respect to any U.S. Holder, such Holder becoming disabled under one of the Company’s long-term disability plans or becoming eligible for benefits from the Social Security Administration. For all non-U.S. Holders, Disability shall mean the Holder is incapacitated for a period of at least 180 days by accident, sickness or other circumstance that renders such Holder mentally or physically incapable of performing the material duties and services required of the Holder in the Holder’s position with the Company on a full-time basis during such period.

(c)    Good Reason. For purposes of this Award, “Good Reason” shall have the meaning set forth in any then applicable employment or other similar written agreement (including such similar term or concept, as determined by the Committee) between the Holder and the Company or an Affiliate. If there is no such written agreement or if such agreement does not define “Good Reason,” then “Good Reason” shall mean the Holder has complied with the Good Reason Process (as defined below) following the occurrence of any of the following conditions (without the Holder’s written consent or waiver): (i) a material diminution in the Holder’s responsibilities, authority or duties, unless such diminution is in connection with a Cause event; (ii) a diminution in the Holder’s annual base salary or target annual bonus opportunity; (iii) during the 24-month period following a Change in Control, a material diminution in the regular target annual long term incentive opportunity or the annual target long-term incentive award subsequently granted to the Holder in an amount less than the regular target opportunity, but in all cases disregarding the equity awards granted in connection with the Company’s going-public transaction in 2018 and other special cash or equity awards; (iv) a material change in the geographic location at which the Holder provides services to the Company; or (v) a material breach of any employment or other material agreement between the Company or one of its Affiliates and the Holder. For purposes of this Award, “Good Reason Process” shall mean that (i) the Holder reasonably determines in good faith that a Good Reason condition has occurred; (ii) the Holder notifies the Company in writing of the occurrence of the Good Reason condition within 60 days of the Holder having actual or

constructive knowledge of the occurrence of such condition; (iii) the Holder cooperates in good faith with the Company’s efforts, for a period not less than 30 days following such notice (the “Cure Period”), to remedy the condition; (iv) notwithstanding such efforts, the Good Reason condition continues to exist; and (v) the Holder terminates Holder’s Employment at least 10 days, but no more than 60 days, after the end of the Cure Period. For the avoidance of doubt, if the Company cures the Good Reason condition during the Cure Period, Good Reason shall be deemed not to have occurred.

4.Issuance or Delivery of Shares. Except as otherwise provided for herein, the Company shall issue any shares that have become vested pursuant to this Award within 60 days after such shares become vested. Such issuance or delivery shall be evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company. The Company shall pay all original issue or transfer taxes and all fees and expenses incident to such issuance or delivery, except as otherwise provided in Section 7. Prior to the issuance to the Holder of Common Shares subject to the Award, the Holder shall have no direct or secured claim in any specific assets of the Company or in such Common Shares, and will have the status of a general unsecured creditor of the Company..

5.Clawback of Proceeds.

5.1.    Clawback of Proceeds. This award is subject to the clawback provisions in Section 5.14 of the Plan.

5.2.    Right of Setoff. The Holder agrees that by accepting the Award the Holder authorizes the Company and its Affiliates to deduct any amount or amounts owed by the Holder pursuant to this Section 5 from any amounts payable by or on behalf of the Company or any affiliate to the Holder, including, without limitation, any amount payable to the Holder as salary, wages, vacation pay, bonus or the vesting or settlement of the Award or any share-based award. This right of setoff shall not be an exclusive remedy and the Company’s or an Affiliate’s election not to exercise this right of setoff with respect to any amount payable to the Holder shall not constitute a waiver of this right of setoff with respect to any other amount payable to the Holder or any other remedy.

6.Transfer Restrictions and Investment Representation.

6.1. Nontransferability of Award. The Award shall not be transferable other than by will, the laws of descent and distribution or pursuant to beneficiary designation procedures approved by the Company. Except to the extent permitted by the foregoing sentence, the Award may be exercised or settled during the Holder’s lifetime only by the Holder or the Holder’s legal representative or similar person. Except as permitted by the second preceding sentence, the Award may not be sold, transferred, assigned, pledged, hypothecated, encumbered or otherwise disposed of (whether by operation of law or otherwise) or be subject to execution, attachment or similar process. Upon any attempt to so sell, transfer, assign, pledge, hypothecate, encumber or otherwise dispose of the Award, such Award and all rights hereunder shall immediately become null and void. All transfer restrictions provided for in this Section 6.1, shall lapse when the Common Shares are issued or delivered to the Holder.

6.2.     Investment Representation. The Holder hereby covenants that (a) any sale of any Common Share acquired upon the vesting of the Award shall be made either pursuant to an effective registration statement under the Securities Act of 1933, as amended (the “Securities Act”)

and any applicable state securities laws, or pursuant to an exemption from registration under the Securities Act and such state securities laws and (b) the Holder shall comply with all regulations and requirements of any regulatory authority having control of or supervision over the issuance of the shares and, in connection therewith, shall execute any documents which the Committee shall in its sole discretion deem necessary or advisable.

7.    Additional Terms and Conditions of Award.

7.1.    Survival of Other Severance Benefits and Non-Duplication. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the severance benefits provided under Section 3.2 and Section 3.3 (the “Severance Benefits”) are not meant to replace or supersede any similar severance benefits provided under the Sirius Group Severance and Change in Control Plan or any employment agreement, arrangement or award agreement or any other similar contractual arrangement (“Other Severance Benefits”) and the Severance Benefits provided under this Agreement are not intended to result in any duplicative benefits to the Holder and this Agreement shall be administered accordingly. For the avoidance of doubt, this Section 7.1 is not meant to impinge or interfere with the Company’s ability to require the Holder to follow or adhere to any steps or requirements under this Agreement or Other Severance Benefits to obtain severance benefits contemplated thereunder (e.g., executing any releases, complying with any restrictive covenants, etc.).

7.2.    Withholding Taxes. Subject to Section 5.5 of the Plan, as a condition precedent to the issuance or delivery of the Common Shares, either (i) the Holder shall, upon request by the Company, pay to the Company such amount as the Company (or an Affiliate) may be required, under all applicable federal, state, local, foreign or other laws or regulations, to withhold and pay over as income or other withholding taxes (the “Required Tax Payments”) with respect to the Award or (ii) the Company (or an Affiliate) may, in its discretion, deduct any Required Tax Payments from any amount then or thereafter payable by the Company (or an affiliate) to the Holder, which may include the withholding of whole Common Shares, which would otherwise be delivered to the Holder having an aggregate Fair Market Value, determined as of the date on which such withholding obligation arises, equal to the Required Tax Payments, in either case in accordance with such terms, conditions and procedures that may be prescribed by the Company. A determination by the Company to satisfy the Required Tax Payments by withholding Common Shares shall be made by the Committee if the Holder is subject to Section 16 of the Exchange Act.

7.3.    Compliance with Applicable Law. The Award is subject to the condition that if the listing, registration or qualification of the Common Shares subject to the Award upon any securities exchange or under any law, or the consent or approval of any governmental body, or the taking of any other action is necessary or desirable as a condition of, or in connection with, the delivery of shares hereunder, the Common Shares subject to the Award shall not be delivered, in whole or in part, unless such listing, registration, qualification, consent, approval or other action shall have been effected or obtained, free of any conditions not acceptable to the Company. The Company agrees to use reasonable efforts to effect or obtain any such listing, registration, qualification, consent, approval or other action.

7.4.    Award Confers No Rights to Continued Employment. In no event shall the granting of the Award or its acceptance by the Holder, or any provision of this Agreement or the Plan, give or be deemed to give the Holder any right to continued employment by the Company or any Affiliate or

affect in any manner the right of the Company or any Affiliate to terminate the employment of any person at any time.

7.5.    No Mitigation. In no event shall Holder be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Holder under any of the provisions of this Agreement and, such amounts shall not be reduced whether or not the Holder obtains other employment.

7.6.    Decisions of Board or Committee. The Board or the Committee shall have the right to resolve all questions, which may arise in connection with the Award. Any interpretation, determination or other action made or taken by the Board or the Committee regarding the Plan or this Agreement shall be final, binding and conclusive.

7.7.    Successors. This Agreement shall be binding upon and inure to the benefit of the Company and any successor of the Company, including without limitation any person, association, or entity which may hereafter acquire or succeed to all or substantially all of the business or assets of the Company by any means whether direct or indirect, by purchase, merger, consolidation, or otherwise and the Company shall require any such acquirer successor to assume this Agreement and the obligations and liabilities contemplated hereunder. Holder’s rights, benefits and obligations under this Agreement are personal and shall not be voluntarily or involuntarily assigned, alienated, or transferred, whether by operation of law or otherwise, without the prior written consent of the Company.

7.8.    Notices. All notices, requests or other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given when personally delivered or when mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows:

If to the Company: Sirius International Insurance Group, Ltd.

14 Wesley Street, 5th Floor

Hamilton HM11 Bermuda

Attention: Group General Counsel

If to the Holder: At the most recent address on file with the Company

or to such other address as either party may furnish to the other in writing in accordance herewith, except that notices of changes of address shall be effective only upon receipt.

7.9.    Governing Law. This Agreement, the Award and all determinations made and actions taken pursuant hereto and thereto, to the extent not otherwise governed by the Code or the laws of the United States and/or Bermuda, shall be governed by the laws of New York and construed in accordance therewith without giving effect to principles of conflicts of laws.

7.10.    Agreement Subject to the Plan. This Agreement is subject to the provisions of the Plan and shall be interpreted in accordance therewith. In the event that the provisions of this Agreement and the Plan conflict, the Plan shall control. The Holder hereby acknowledges receipt of a copy of the Plan.

7.11.    Entire Agreement. Subject to Section 7.1, this Agreement constitutes the entire agreement of the parties with respect to the subject matter hereof and supersedes in its entirety all prior undertakings and agreements of the Company and the Holder with respect to the subject matter hereof, and may not be modified adversely to the Holder’s interest except by means of a writing signed by the Company and the Holder. Notwithstanding the foregoing, to the extent the Holder was subject to restrictive covenants prior to the execution of this Agreement, such restrictive covenants shall continue to remain in full force and effect with respect to any conduct or actions prior to the execution of this Agreement.

7.12.    Severability. If a court of competent jurisdiction determines that any provision of this Agreement is invalid or unenforceable, then the invalidity or unenforceability of that provision shall not affect the validity or enforceability of any other provision of this Agreement, and all other provisions shall remain in full force and effect.

7.13.    Amendment and Waiver. The Company may amend the provisions of this Agreement at any time; provided that an amendment that would adversely affect the Holder’s rights under this Agreement shall be subject to the written consent of the Holder. No course of conduct or failure or delay in enforcing the provisions of this Agreement shall affect the validity, binding effect or enforceability of this Agreement.

7.14.    Compliance with Section 409A of the Code. This Award is intended to be exempt from or comply with Section 409A of the Code, and shall be interpreted and construed accordingly. To the extent this Agreement provides for the Award to become vested and be settled upon the Holder’s termination of employment, the applicable Common Shares shall be transferred to the Holder or his or her beneficiary upon the Holder’s “separation from service,” within the meaning of Section 409A of the Code; provided that if the Holder is a “specified employee,” within the meaning of Section 409A of the Code, then to the extent the Award constitutes nonqualified deferred compensation, within the meaning of Section 409A of the Code, such Common Shares shall be transferred to the Holder or his or her beneficiary upon the earlier to occur of (i) the six-month anniversary of such separation from service and (ii) the date of the Holder’s death.

7.15.    Survival. If the Holder has executed the Restrictive Covenant Agreement prior to the date hereof, then, the provisions of this Agreement related to the Restrictive Covenant Agreement shall survive and remain binding and enforceable, notwithstanding the expiration or termination of this Plan, the termination of a Holder’s employment for any reason or any settlement of the financial rights and obligations arising from such Holder’s participation hereunder, to the extent necessary to preserve the intended benefits of such provisions.

7.16.    Unfunded Status of Awards; No Trust of Fund Created. The Plan is intended to constitute an “unfunded” plan for certain incentive awards. Neither the Plan nor any award shall create or be construed to create a trust or separate fund of any kind or a fiduciary relationship between the Company or any Affiliate and a participant or any other person. To the extent that any person acquires a right to receive payments from the Company or any Affiliate pursuant to an award, such right shall be no greater than the right of any general unsecured creditors of the Company or such Affiliate.

EX-10.9.7

Exhibit 10.9.7 

July 16, 2020

Gene Boxer

Executive Vice President, Chief Strategy Officer, and Group General Counsel

RESERVED

Re: Payment of Cash Awards

Dear Gene:

The purpose of this letter is to confirm certain actions taken by the Compensation Committee of the Board of Directors of Sirius International Insurance Group, Ltd. (the “Company”) on July 10, 2020 relating to your special cash retention award and annual cash incentive award opportunity for the current calendar year, each as further described below.

1.    Retention Award

As you know, in November 2019, you received a special cash retention award in the amount of $1,000,000 (the “Retention Award”). The Retention Award was scheduled to vest in two equal installments on March 15, 2020 and March 15, 2021, and be paid in two equal installments on or prior to such respective dates, subject to your continued employment through the applicable vesting and payment date. You will now be entitled to receive payment of the award, to the extent then unpaid and subject to any applicable withholding and deductions, upon the earlier to occur of (i) December 31, 2020 or (ii) a “Change in Control” (as that term is defined in the Company’s 2018 Omnibus Incentive Plan). In the event that your employment with the Company is terminated within 12 months after the payment date for any reason other than (i) by the Company without Cause (as defined in the Retention Award) or (ii) upon your resignation for Good Reason (as defined in the Sirius Group Severance and Change in Control Plan), you will be required to repay to the Company any payment made to you (less applicable withholding and deductions) within 30 days after the date of your termination.

2.    Annual Incentive Award

As you know, the Company maintains an annual cash incentive program, pursuant to which you are eligible for a cash incentive opportunity for the 2020 calendar year (the “Incentive Award”). Incentive Awards under the program are generally payable in March of the year following the year to which the award relates. You will now be entitled to receive your Incentive Award payable at the target amount $700,000 for the 2020 calendar year, subject to any applicable withholding and deductions, upon the earlier to occur of (i) December 31, 2020 or (ii) a “Change in Control” (as that term is defined in the Company’s 2018 Omnibus Incentive Plan).

* * *

Please indicate your acceptance of the terms and conditions of this letter by returning a signed copy of this letter to my attention. If you have any questions, please feel free to contact me.

This letter agreement may be executed in any number of counterparts (including by means of facsimile or e-mail in .pdf format), each of which of this letter agreement and all of which, when taken together, will be deemed to constitute one and the same agreement.

Sincerely yours,

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

__/s/ Kernan V. Oberting_________________________

By: Kernan V. Oberting

Title: President and Chief Executive Officer

Acknowledgment, Acceptance and Agreement:

/s/ Gene Boxer

Gene Boxer

7/17/2020    

Date

EX-10.9.8

Exhibit 10.9.8

July 16, 2020

Kernan V. Oberting

President and Chief Executive Officer

RESERVED

Re: Payment of Cash Awards

Dear Kip:

The purpose of this letter is to confirm certain actions taken by the Compensation Committee of the Board of Directors of Sirius International Insurance Group, Ltd. (the “Company”) on July 10, 2020 relating to your special cash retention award and annual cash incentive award opportunity for the current calendar year, each as further described below.

1.    Retention Award

As you know, in February 2020, you received a special cash retention award in the amount of $3,060,000 (the “Retention Award”). The Retention Award was scheduled to vest in two equal installments on March 15, 2020 and March 15, 2021, and be paid in two equal installments on or prior to such respective dates, subject to your continued employment through the applicable vesting and payment date. You will now be entitled to receive payment of the award, to the extent then unpaid and subject to any applicable withholding and deductions, upon the earlier to occur of (i) December 31, 2020 or (ii) a “Change in Control” (as that term is defined in the Company’s 2018 Omnibus Incentive Plan). In the event that your employment with the Company is terminated within 12 months after the payment date for any reason other than (i) by the Company without Cause (as defined in the Retention Award) or (ii) upon your resignation for Good Reason (as defined in the Sirius Group Severance and Change in Control Plan), you will be required to repay to the Company any payment made to you (less applicable withholding and deductions) within 30 days after the date of your termination.

2.    Annual Incentive Award

As you know, the Company maintains an annual cash incentive program, pursuant to which you are eligible for a cash incentive opportunity for the 2020 calendar year (the “Incentive Award”). Incentive Awards under the program are generally payable in March of the year following the year to which the award relates. You will now be entitled to receive your Incentive Award payable at the target amount $1,000,000 for the 2020 calendar year, subject to any applicable withholding and deductions, upon the earlier to occur of (i) December 31, 2020 or (ii) a “Change in Control” (as that term is defined in the Company’s 2018 Omnibus Incentive Plan).

* * *

Please indicate your acceptance of the terms and conditions of this letter by returning a signed copy of this letter to my attention. If you have any questions, please feel free to contact me.

This letter agreement may be executed in any number of counterparts (including by means of facsimile or e-mail in .pdf format), each of which of this letter agreement and all of which, when taken together, will be deemed to constitute one and the same agreement.

Sincerely yours,

SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.

____/s/ Gene Boxer _______________________

By: Gene Boxer

Title: Group General Counsel

Acknowledgment, Acceptance and Agreement:    

/s/ Kernan V. Oberting            

Kernan V. Oberting

July 21, 2020        

Date

EX-31.1

Exhibit 31.1 

Certification

Sirius International Insurance Group, Ltd.

Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 

I, Kernan "Kip" V. Oberting, certify that:

1.I have reviewed this Quarterly Report on Form 10-Q of Sirius International Insurance Group, Ltd.; 

2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report; 

3.Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report; 

4.The registrant’s other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) internal control over financial reporting (as defined by Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

a.Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

b.Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

c.Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation;

d.Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

5.The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions): 

a.All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report financial information; and 

b.Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

Date:	November 9, 2020
By:	/s/ KERNAN "KIP" V. OBERTING
Name:	Kernan "Kip" V. Oberting
Title:	President and Chief Executive Officer

EX-31.2

Exhibit 31.2 

Certification

Sirius International Insurance Group, Ltd.

Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 

I, Ralph A. Salamone, certify that:

1.I have reviewed this Quarterly Report on Form 10-Q of Sirius International Insurance Group, Ltd.; 

2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report; 

3.Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report; 

4.The registrant’s other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) internal control over financial reporting (as defined by Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

a.Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

b.Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

c.Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation;

d.Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

5.The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions): 

a.All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report financial information; and 

b.Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

Date:	November 9, 2020
By:	/s/ RALPH A. SALAMONE
Name:	Ralph A. Salamone
Title:	Chief Financial Officer

EX-32.1

Exhibit 32.1 

Sirius International Insurance Group, Ltd.

Certification Pursuant to Chapter 63, Title 18 United States Code §1350

As Adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 

In connection with the Quarterly Report of Sirius International Insurance Group, Ltd. (the "Company") on Form 10-Q for the quarter ended September 30, 2020, as filed with the Securities and Exchange Commission on the date hereof (the "Report"), I, Kernan "Kip" V. Oberting, President and Chief Executive Officer of the Company, certify pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that to my knowledge:

(1)The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and 

(2)The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

Date:	November 9, 2020
By:	/s/ KERNAN "KIP" V. OBERTING
Name:	Kernan "Kip" V. Oberting
Title:	President and Chief Executive Officer

A signed original of this written statement required by Section 906 has been provided to Sirius International Insurance Group, Ltd. and will be retained by Sirius International Insurance Group, Ltd. and furnished to the Securities and Exchange Commission or its staff upon request.

EX-32.2

Exhibit 32.2 

Sirius International Insurance Group, Ltd.

Certification Pursuant to Chapter 63, Title 18 United States Code §1350

As Adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 

In connection with the Quarterly Report of Sirius International Insurance Group, Ltd. (the "Company") on Form 10-Q for the quarter ended September 30, 2020, as filed with the Securities and Exchange Commission on the date hereof (the "Report"), I, Ralph A. Salamone, Chief Financial Officer of the Company, certify pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that to my knowledge:

(1)The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and 

(2)The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

Date:	November 9, 2020
By:	/s/ RALPH A. SALAMONE
Name:	Ralph A. Salamone
Title:	Chief Financial Officer

A signed original of this written statement required by Section 906 has been provided to Sirius International Insurance Group, Ltd. and will be retained by Sirius International Insurance Group, Ltd. and furnished to the Securities and Exchange Commission or its staff upon request.

EX-99.1

Execution Version

CONFIDENTIAL

TRANSACTION AGREEMENT

by and among

THIRD POINT REINSURANCE LTD.,

and

THE PREFERRED SHAREHOLDERS NAMED HEREIN

September 4, 2020

TABLE OF CONTENTS

		Page
Article 1.	Transactions	2
	Section 1.01 [Reserved]	2
	Section 1.02 Closing — Exchange.	2
Article 2.	[Reserved].	3
Article 3.	Representations and Warranties and Certain Covenants of TPRe	3
	Section 3.01 Organization; Standing.	3
	Section 3.02 Capitalization.	4
	Section 3.03 Authority; Noncontravention; Voting Requirement.	4
	Section 3.04 Governmental Approvals.	5
	Section 3.05 Sale of Securities.	5
Article 4.	Representations and Warranties and Certain Covenants of the Preferred
	Shareholders	5
	Section 4.01 Organization; Standing.	5
	Section 4.02 Authorization; No Breach.	6
	Section 4.03 Governmental Approvals.	6
	Section 4.04 Ownership of the Series B Preference Shares.	6
	Section 4.05 Acquisition for Investment.	6
	Section 4.06 Restricted Securities.	7
	Section 4.07 Accredited Investor.	7
	Section 4.08 Confidential Information.	7
	Section 4.09 Evaluation of and Ability to Bear Risks.	7
	Section 4.10 Non-Reliance.	7
Article 5.	Covenants and Agreements.	8
	Section 5.01 Press Release and Announcements.	8
	Section 5.02 Further Assurances.	8
	Section 5.03 Certain Covenants of TPRe.	8
	Section 5.04 Efforts.	9
	Section 5.05 Registration Rights.	9
	Section 5.06 Stock Exchange Listing.	9

i

	Section 5.07 Credit Rating.	9
	Section 5.08 Approvals.	9
	Section 5.09 Bermuda Monetary Authority Review.	10
Article 6.	Conditions to the Obligations of the Parties at the Closing.	10
	Section 6.01 Conditions to the Obligations of TPRe at the Closing.	10
	Section 6.02 Conditions to the Obligations of the Preferred Shareholders at the
	Closing	10
Article 7.	Mutual Release and Additional Agreements.	10
	Section 7.01 Mutual Release.	10
	Section 7.02 Additional Agreements.	11
	Section 7.03 Confidentiality.	12
Article 8.	Definitions.	13
Article 9.	Miscellaneous.	16
	Section 9.01 No Survival of Representations or Warranties..	16
	Section 9.02 Termination.	16
	Section 9.03 Preferred Shareholder Consents.	17
	Section 9.04 Fees and Expenses.	17
	Section 9.05 Remedies.	17
	Section 9.06 Waivers and Amendments.	17
	Section 9.07 Successors and Assigns.	17
	Section 9.08 Severability.	17
	Section 9.09 Counterparts.	18
	Section 9.10 Descriptive Headings; Interpretation.	18
	Section 9.11 Entire Agreement.	18
	Section 9.12 No Third Party Beneficiaries.	18
	Section 9.13 Governing Law; Jurisdiction; WAIVER OF JURY TRIAL	18
	Section 9.14 Notices.	19
	Section 9.15 No Strict Construction.	20

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SCHEDULES

Schedule I    –    Preference Shares and Ownership Percentages

ANNEXES

Annex A    –    Registration Rights

EXHIBITS

Exhibit A    –    Form of Certificate of Designation of Series B Preference Shares of SiriusPoint

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TRANSACTION AGREEMENT

THIS TRANSACTION AGREEMENT (this “Agreement”) is made and entered into as of September 4, 2020, by and among (i) Third Point Reinsurance Ltd., a Bermuda exempted company limited by shares (“TPRe”), (ii) Bain Capital Special Situations Asia, L.P., a Cayman Islands limited partnership (“Bain”), (iii) CCOF Master, L.P., a Delaware limited partnership (“Carlyle”), (iv) Centerbridge Credit Partners Master, LP, a Delaware limited partnership, and Centerbridge Special Credit Partners III, LP, a Delaware limited partnership (collectively, “Centerbridge”), and (v) GPC Partners Investments (Canis) LP, a Delaware limited partnership (“Gallatin” and, together with Bain, Carlyle and Centerbridge, collectively, the “Preferred Shareholders”). TPRe and the Preferred Shareholders are collectively referred to herein as the “Parties” and individually as a “Party.” Capitalized terms used herein have the meanings given to such terms in Article 8.

WHEREAS, Sirius International Insurance Group, Ltd. (the “Company”), TPRe and Yoga Merger Sub Limited, a Bermuda exempted company limited by shares and a wholly owned Subsidiary of TPRe (“Merger Sub”), are party to that certain Agreement and Plan of Merger (the “Merger Agreement”), dated as of August 6, 2020, pursuant to which, among other things, Merger Sub will merge with and into the Company, with the Company surviving as a wholly owned subsidiary of TPRe (the “Merger”). Upon the closing of the Merger, TPRe will change its corporate name to SiriusPoint, Ltd. (“SiriusPoint”);

WHEREAS, that certain Certificate of Designation of Series B Preference Shares of the Company (the “Series B Certificate of Designation”), dated November 5, 2018, sets forth the designations, preferences and privileges, voting, relative, participating, optional and other special rights, and qualifications, limitations and restrictions of the Series B Preference Shares in addition to those set forth in the Memorandum of Association of the Company and the Bye-Laws of the Company;

WHEREAS, as of the date hereof, the Preferred Shareholders collectively own 100% of the issued and outstanding Series B Preference Shares;

WHEREAS, the Preferred Shareholders have made certain claims against the Company, including under the Series B Certificate of Designation (which include, without limitation, those claims referenced and arising from the matters discussed in the redemption notices and related correspondence sent by the Preferred Shareholders to the Company and to the board of directors of the Company (the “Company Board”) dated April 12, 2020 and April 13, 2020, and in letters from Kirkland & Ellis LLP to the Company Board dated March 30, 2020, May 16, 2020 and May 27, 2020) (collectively, the “Potential Claims”);

WHEREAS, the Parties have discussed and negotiated a proposal intended to satisfy the change in control payment obligation set forth in the Series B Certificate of Designation and to resolve and release all Potential Claims previously asserted under the Series B Certificate of Designation against the Company; and

WHEREAS, on the terms and subject to the conditions set forth in this Agreement, concurrent with or immediately following the consummation of the Merger and the other transactions contemplated by the Merger Agreement, at the Closing, in full satisfaction of the Potential Claims, TPRe and the Preferred Shareholders desire to effect the exchange of all outstanding Series B Preference Shares held by the Preferred Shareholders, in such amounts to be determined in accordance herewith, for newly designated and issued Series B preference shares, par value of $0.10 per share, of SiriusPoint (“SiriusPoint Preference Shares”) and, at TPRe’s election, for the Cash Payment Amount (defined below).

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NOW, THEREFORE, in consideration of the mutual covenants, agreements and understandings contained herein, and intending to be legally bound, the Parties hereby agree as follows:

Article 1.    Transactions.

Section 1.01    [Reserved].

Section 1.02    Closing — Exchange.

(a)    Exchange. On the terms and subject to the conditions set forth in this Agreement, at the Closing, (i) TPRe shall pay or issue and deliver to the Preferred Shareholders (A) cash in such amount as it shall determine in its discretion (the “Cash Payment Amount”) (provided, that if the Cash Payment Amount is less than the Total Payment Amount, the Cash Payment Amount may not exceed $60,000,000) plus (B) a number of duly authorized, validly issued, fully paid and non-assessable SiriusPoint Preference Shares (the “Exchange Shares”), having the terms and conditions set forth in the certificate of designation of TPRe substantially in the form attached hereto as Exhibit A (the “SiriusPoint Certificate of Designation”), in an amount that, when the aggregate Liquidation Preference (as defined in the SiriusPoint Certificate of Designation) of the Exchange Shares is added to the Cash Payment Amount, it will equal the sum of (x) an aggregate of $260,000,000 plus (y) to the extent Closing occurs after May 6, 2021, $1,875,000 per month (or a pro rata amount for a portion of such month) from May 6, 2021 through the Closing (the “Total Payment Amount”), and (ii) the Preferred Shareholders shall surrender to TPRe, in exchange for the Exchange Shares, all of the outstanding Series B Preference Shares held by the Preferred Shareholders (the “Exchange”). The number of Series B Preferences Shares to be issued and delivered (the “Exchange Amount”) shall equal the quotient of (x) (A) the Total Payment Amount minus (y) the Cash Payment Amount, divided by (y) $25.00. The number of Exchange Shares to be issued to each Preferred Shareholder in the Exchange shall equal the product of (x) the Exchange Amount multiplied by (y) such Preferred Shareholder’s pro rata ownership percentage as set forth on Schedule I of this Agreement, in column III. The amount of cash to be paid to each Preferred Shareholder in the Exchange shall equal the product of (x) the Cash Payment Amount multiplied by (y) such Preferred Shareholder’s pro rata ownership percentage as set forth on Schedule I of this Agreement, in column III. If the Cash Payment Amount is less than the Total Payment Amount, at the Closing, TPRe shall deliver to each Preferred Shareholder the applicable number of Exchange Shares registered in the name of such Preferred Shareholder, free and clear of all Encumbrances, and shall record such Preferred Shareholder as the owner of such Exchange Shares on the books and records of TPRe. In addition, on or prior to the Closing, TPRe shall (i) execute and deliver to the Preferred Shareholders a copy of the SiriusPoint Certificate of Designation, duly executed by TPRe, and (ii) file the SiriusPoint Certificate of Designation with the Registrar as required under the Bermuda Companies Act. Unless this Agreement is terminated or TPRe or SiriusPoint fail to comply with their obligations to consummate the Exchange as contemplated hereby, each Preferred Shareholder agrees that it shall not exercise any right to require the Company to redeem its Series B Preference Shares pursuant to Section 6 of the Series B Certificate of Designation; provided that this sentence shall not apply to the Preferred Shareholders to the extent TPRe has terminated the Merger Agreement or filed suit or delivered a written notice seeking to terminate the Merger Agreement.

(b)    [Reserved]

(c)    Procedures for Exchange. The number of Series B Preference Shares to be surrendered by each Preferred Shareholder in exchange for the Cash Payment Amount and the Exchange Shares in the Exchange is set forth on Schedule I of this Agreement, in column II, which represents all of the Series B Preference Shares beneficially owned by such Preferred Shareholder. Each Preferred Shareholder hereby acknowledges and agrees that as a result of the Exchange, the Series B Preference Shares held by such

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Preferred Shareholder shall be cancelled and shall cease to be issued and outstanding. To the extent applicable, at the Closing, each Preferred Shareholder shall deliver to TPRe stock certificates evidencing the outstanding Series B Preference Shares held by such Preferred Shareholder for cancellation, or an affidavit of lost certificate in customary form. The Parties shall work in good faith to prepare a written calculation of the Exchange Amount and the number of Exchange Shares to be issued to each Preferred Shareholder in the Exchange or, if TPRe elects to pay the Cash Payment Amount, a written calculation of the Cash Payment Amount and the portion of the Cash Payment Amount to be paid to each Preferred Shareholder, no later than five (5) Business Days prior to the Closing. If TPRe elects to make any Cash Payment Amount, at the Closing, TPRe shall deliver the applicable portion of the Cash Payment Amount to each Preferred Shareholder by wire transfer of immediately available U.S. federal funds, to an account designated by such Preferred Shareholder in writing.

(d)    No Fractional Shares. Notwithstanding any provision of this Agreement to the contrary, no fraction of a SiriusPoint Preference Share may be issued in connection with the Exchange and no dividends or other distributions with respect to SiriusPoint Preference Shares shall be payable on or with respect to any such fractional share and no such fractional share will entitle the owner thereof to vote or to any rights of a shareholder of TPRe or SiriusPoint. In lieu of the issuance of any such fractional SiriusPoint Preference Share, any Preferred Shareholder who would otherwise have been entitled to a fraction of a SiriusPoint Preference Share shall be paid cash, without interest, in an amount equal to the product of (i) the fractional interest in a SiriusPoint Preference Share to which such Preferred Shareholder would otherwise be entitled under this Section 1.02 but for this Section 1.02(d) multiplied by (ii) $25.00. At the Closing, any amounts payable under this Section 1.02(d) to any Preferred Shareholder shall be paid by TPRe by wire transfer of immediately available U.S. federal funds to an account designated by such Preferred Shareholder in writing.

(e)    [Reserved].

(f)    Closing. Subject to the satisfaction or waiver of the conditions set forth in Article 6, the closing of the transactions described in this Section 1.02 (collectively, the “Transactions”) shall occur concurrent with or immediately following the consummation of the Merger and the other transactions contemplated by the Merger Agreement, to occur at the closing thereof by means of email or other electronic transmission (the “Closing”), or at such other date, time or place as the Parties agree in writing (the date on which the Closing occurs is referred to herein as the “Closing Date”).

Article 2.    [Reserved].

Article 3.Representations and Warranties and Certain Covenants of TPRe. As a material inducement to the Preferred Shareholders to enter into this Agreement and consummate the transactions contemplated hereby, TPRe hereby represents and warrants (and, in the case of Section 3.03(a), covenants) to the Preferred Shareholders as of the date hereof and as of the Closing Date as follows, except as disclosed in any report, schedule, form, statement or other document (including exhibits) filed with, or furnished to, the U.S. Securities and Exchange Commission (“SEC”) since January 1, 2019 by TPRe and publicly available at least three (3) Business Day prior to the date hereof (the “TPRe SEC Documents”), other than disclosures contained in the “Risk Factors” or “Forward-Looking Statements” sections of such TPRe SEC Documents or that otherwise constitute risk factors or forward-looking statements; provided, that the disclosures therein shall not be deemed to qualify any representations and warranties made in Section 3.01, Section 3.02 or Section 3.03:

Section 3.01    Organization; Standing.

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(a)    Each of TPRe and its Subsidiaries (i) is a corporation or other legal entity, duly incorporated or organized, validly existing and in good standing (with respect to jurisdictions that recognize such concept) under the Laws of its jurisdiction of incorporation or organization, (ii) has full corporate or similar power and authority to own, lease and operate its properties, rights and assets and to conduct its business as presently conducted, and (iii) is duly qualified or licensed to do business as a foreign corporation and is in good standing (with respect to jurisdictions that recognize such concept) in each jurisdiction where the character of the properties owned, leased or operated by it or the nature of its business makes such qualification or licensing necessary, except, in the case of clause (iii), where such failure would not, individually or in the aggregate, reasonably be likely to have a TPRe Material Adverse Effect.

(b)    A true and correct copy of each of the TPRe Organizational Documents is included in the TPRe SEC Documents. TPRe is not in violation of any provisions of the TPRe Organizational Documents.

Section 3.02    Capitalization. The representations and warranties of TPRe in Section 4.02 of the Merger Agreement were, as of the date of the Merger Agreement, true and correct in all respects. Between the date of the Merger Agreement and the date hereof, neither TPRe nor any of its Subsidiaries has taken, authorized, or committed or agreed (in writing or otherwise) to take, any of the actions described in Sections 5.01(b)(i), (ii), (iii) or (iv) of the Merger Agreement.

Section 3.03    Authority; Noncontravention; Voting Requirement.

(a)    TPRe has all necessary power and authority to execute and deliver this Agreement and to perform its obligations hereunder and to consummate the Transactions. The execution, delivery and performance by TPRe of this Agreement and the SiriusPoint Certificate of Designation, and the consummation by TPRe of the Transactions, will be or have been, as applicable, on or prior to September 11, 2020, duly authorized and approved by the TPRe Board and, except for such authorization by the TPRe Board, executing and delivering the SiriusPoint Certificate of Designation, filing the SiriusPoint Certificate of Designation with the Registrar pursuant to the Bermuda Companies Act, and the corporate actions necessary to consummate the Merger, no other corporate action on the part of TPRe is necessary to authorize the execution, delivery and performance by TPRe of this Agreement and the SiriusPoint Certificate of Designation and the consummation by TPRe of the Transactions. This Agreement has been duly executed and delivered by TPRe and, assuming due authorization, execution and delivery hereof by the other Parties, constitutes a legal, valid and binding obligation of TPRe, enforceable against TPRe in accordance with its terms, except that such enforceability (i) may be limited by bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium, rehabilitation, conservatorship, liquidation, receivership and other similar Laws of general application affecting or relating to the enforcement of creditors’ rights generally and (ii) is subject to general principles of equity, whether considered in a proceeding at law or in equity (clauses (i) and (ii), collectively, the “Bankruptcy and Equity Exception”).

(b)    [Reserved].

(c)    Neither the execution and delivery of this Agreement by TPRe, nor the consummation by TPRe of the Transactions, nor performance or compliance by TPRe with any of the terms or provisions hereof, will (i) conflict with or violate any provision of (A) the TPRe Organizational Documents or (B) the similar organizational documents of any of TPRe’s Subsidiaries in any material respect or (ii) assuming (A) compliance with the matters set forth in Section 4.02(b) (other than Section 4.02(b)(ii) but including (ii)(x) and (ii)(y) thereof) (and assuming the accuracy of the representations and warranties made in such Section 4.02(b)), (B) that the actions described in Section 3.03(a) have been completed, (C) that the Consents referred to in Section 3.04 are obtained and (D) that the filings referred to in Section 3.04 are

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made, in the case of each of the foregoing clauses (A) through (D), prior to the Closing, (x) violate any Law applicable to TPRe or any of its Subsidiaries in any material respect, (y) require any consent or notice, or result in any violation or breach of, or conflict with, or constitute (with or without notice or lapse of time or both) a default (or give rise to any right of purchase, termination, amendment, acceleration or cancellation) under, result in the loss of any benefit under, or result in the triggering of any payments pursuant to, any of the terms, conditions or provisions of any material Contract of TPRe or (z) result in the creation of any Lien other than a Permitted Lien on any properties or assets of TPRe or any of its Subsidiaries, except, in the case of clauses (ii)(y) and (ii)(z), as would not, individually or in the aggregate, reasonably be likely to have a TPRe Material Adverse Effect.

(d)    Other than the votes and approvals necessary to consummate the Merger, no votes or approvals of the holders of any class or series of share capital of TPRe or any of its Subsidiaries are necessary to approve this Agreement, the SiriusPoint Certificate of Designation and the Transactions.

Section 3.04    Governmental Approvals. Except for (a) compliance with the rules and regulations of the NYSE, (b) the filing of the SiriusPoint Certificate of Designation with the Registrar pursuant to the Bermuda Companies Act, (c) compliance with any applicable state securities or blue sky laws and (d) the Consents and filings necessary to consummate the Merger, no Consent of, or filing, declaration or registration with, any Governmental Authority by TPRe is necessary for the execution and delivery of this Agreement by TPRe, the performance by TPRe of its obligations hereunder and the consummation by TPRe of the Transactions, other than such other Consents, filings, declarations or registrations that, if not obtained, made or given, would not, individually or in the aggregate, reasonably be likely to have a TPRe Material Adverse Effect or would not reasonably be likely to prevent, impede, interfere with, hinder or delay in any material respect the ability of TPRe to consummate the Transactions.

Section 3.05    Sale of Securities. Assuming the accuracy of the representations and warranties set forth in Section 4.05, Section 4.06 and Section 4.07, the issuance of the SiriusPoint Preference Shares pursuant to this Agreement is exempt from the registration and prospectus delivery requirements of the Securities Act and the rules and regulations thereunder. Without limiting the foregoing, neither TPRe nor, to the knowledge of TPRe, any other Person authorized by TPRe to act on its behalf, has engaged in a general solicitation or general advertising (within the meaning of Regulation D of the Securities Act) of investors with respect to offers or sales of SiriusPoint Preference Shares, and neither TPRe nor, to the knowledge of TPRe, any Person acting on its behalf has made any offers or sales of any security or solicited any offers to buy any security, under circumstances that would cause the offering or issuance of SiriusPoint Preference Shares under this Agreement to be integrated with prior offerings by TPRe for purposes of the Securities Act that would result in none of Regulation D or any other applicable exemption from registration under the Securities Act to be available, nor will TPRe take any action or step that would cause the offering or issuance of SiriusPoint Preference Shares under this Agreement to be integrated with other offerings by TPRe.

Article 4.    Representations and Warranties and Certain Covenants of the Preferred Shareholders. As a material inducement to TPRe to enter into this Agreement and consummate the transactions contemplated hereby, each Preferred Shareholder (on an individual basis solely with respect to itself and not jointly and severally) hereby represents and warrants (and, in the case of Section 4.04, covenants) to TPRe as of the date hereof and as of the Closing Date as follows:

Section 4.01    Organization; Standing. Each such Preferred Shareholder is a legal entity, duly incorporated or organized, validly existing and in good standing (with respect to jurisdictions that recognize such concept) under the Laws of its jurisdiction of incorporation or organization.

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Section 4.02    Authorization; No Breach.

(a)    Each such Preferred Shareholder has all necessary power and authority to execute and deliver this Agreement and to perform its obligations hereunder and to consummate the Transactions. The execution, delivery and performance by such Preferred Shareholder of this Agreement, and the consummation by such Preferred Shareholder of the Transactions, have been duly authorized and approved by such Preferred Shareholder and no other corporate action on the part of such Preferred Shareholder is necessary to authorize the execution, delivery and performance by such Preferred Shareholder of this Agreement and the consummation by such Preferred Shareholder of the Transactions. This Agreement has been duly executed and delivered by such Preferred Shareholder and, assuming due authorization, execution and delivery hereof by the other Parties, constitutes a legal, valid and binding obligation of such Preferred Shareholder, enforceable against such Preferred Shareholder in accordance with its terms, except that such enforceability may be limited by and is subject to the Bankruptcy and Equity Exception.

(b)    Neither the execution and delivery of this Agreement by such Preferred Shareholder, nor the consummation by such Preferred Shareholder of the Transactions, nor performance or compliance by such Preferred Shareholder with any of the terms or provisions hereof, will (i) conflict with or violate any provision of (A) the organizational documents of such Preferred Shareholder in any material respect or (ii) assuming compliance with the matters set forth in Section 3.03(c) (other than Section 3.03(c)(ii)(A)) (and assuming the accuracy of the representations and warranties made in such Section 3.03(c)) prior to the Closing, (x) violate any Law applicable to such Preferred Shareholder in any material respect, (y) require any consent or notice, or result in any violation or breach of, or conflict with, or constitute (with or without notice or lapse of time or both) a default (or give rise to any right of purchase, termination, amendment, acceleration or cancellation) under, result in the loss of any benefit under, or result in the triggering of any payments pursuant to, any of the terms, conditions or provisions of any material Contract of such Preferred Shareholder or (z) result in the creation of any Lien other than a Permitted Lien on any properties or assets of such Preferred Shareholder or any of its Subsidiaries, except, in the case of clauses (ii)(y) and (ii)(z), as would not, individually or in the aggregate, reasonably be likely to have a material adverse effect on such Preferred Shareholder or would not reasonably be likely to prevent, impede, interfere with, hinder or delay in any material respect the ability of such Preferred Shareholder to consummate the Transactions.

Section 4.03    Governmental Approvals. No Consent of, or filing, declaration or registration with, any Governmental Authority by such Preferred Shareholder is necessary for the execution and delivery of this Agreement by such Preferred Shareholder, the performance by such Preferred Shareholder of its obligations hereunder and the consummation by such Preferred Shareholder of the Transactions, other than such other Consents, filings, declarations or registrations that, if not obtained, made or given, would not, individually or in the aggregate, reasonably be likely to have a material adverse effect on such Preferred Shareholder or would not reasonably be likely to prevent, impede, interfere with, hinder or delay in any material respect the ability of such Preferred Shareholder to consummate the Transactions.

Section 4.04    Ownership of the Series B Preference Shares. Each such Preferred Shareholder has good and valid title to the Series B Preference Shares set forth next to such Preferred Shareholder’s name on Schedule I hereto, in column II, free and clear of all Encumbrances. Each Preferred Shareholder agrees not to directly or indirectly sell, dispose of, or otherwise transfer its Series B Preference Shares prior to the Closing, unless the acquirer agrees in writing to be bound by the terms of this Agreement.

Section 4.05    Acquisition for Investment. Each such Preferred Shareholder is acquiring the SiriusPoint Preferred Shares for its own account, for investment and not with a view to, or for sale in connection with, the distribution thereof within the meaning of the Securities Act.

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Section 4.06    Restricted Securities. Each such Preferred Shareholder understands that (i) except as provided on Annex A of this Agreement, the SiriusPoint Preferred Shares will not be registered under the Securities Act or any state securities laws by reason of their issuance by TPRe in a transaction exempt from the registration requirements thereof and (ii) the SiriusPoint Preferred Shares may not be sold unless such disposition is registered under the Securities Act and applicable state securities laws or is exempt from registration thereunder.

Section 4.07    Accredited Investor. Each such Preferred Shareholder is a “Qualified Institutional Buyer” (as defined in Rule 144A of the Securities Act) or is an institutional “accredited investor” (within the meaning of Rule 501(a)(1), (2), (3), (7) and/or (as it pertains to clauses (1), (2), (3) or (7)) (8) of Regulation D promulgated under the Securities Act). Each such Preferred Shareholder has sufficient knowledge and experience in financial and business matters so as to be capable of evaluating the merits and risks of its investment in the Series B Preferred Shares and the SiriusPoint Preferred Shares and is capable of bearing the economic risks of such investment.

Section 4.08    Confidential Information. Each Preferred Shareholder acknowledges that TPRe and its affiliates and their respective directors, officers, employees and controlling persons may be in possession of material non-public information (the “Confidential Information”) regarding the Company or TPRe, respectively, and TPRe is under no obligation to disclose such Confidential Information in connection with the execution and delivery of this Agreement or the consummation of the Exchange. Each such Preferred Shareholder acknowledges that the Confidential Information may be material in respect of the Company or TPRe and their respective financial condition, results of operations, business, properties, assets, liabilities, management, projections, plans or prospects or to a determination of the value of the SiriusPoint Preference Shares and or the Series B Preference Shares and that such value may be substantially different from the consideration contemplated for such securities in this Agreement. Each such Preferred Shareholder acknowledges that TPRe currently does not have any fiduciary duty to any Preferred Shareholder, or any current obligation, fiduciary or otherwise, to disclose to it any Confidential Information. Neither the foregoing nor any other provision of this Agreement shall relieve TPRe or any of its affiliates or any of their respective directors, officers, employees, agents and controlling persons, from any liability in respect of actual fraud or any breach of a representation, warranty or covenant in this Agreement, or release it from any duties owed to its shareholders after the consummation of the Exchange.

Section 4.09    Evaluation of and Ability to Bear Risks Each Preferred Shareholder (a) is experienced, sophisticated and knowledgeable in business and financial matters and in the trading of securities, (b) is able to bear the business, financial and economic risks associated with the transactions contemplated by this Agreement and (c) understands the disadvantage that may result from selling the Series B Preference Shares without knowledge of any Confidential Information. Each such Preferred Shareholder, (a) by reason of its own business or financial experience or its own independent investigation, has the capability, and has information sufficient in order, (i) to make, and has so made, an informed decision on the merits and risks of entering into and consummating the Transactions and (ii) to protect its own interests in connection with the Transactions; (b) has had sufficient information and opportunity for satisfactory consultation, and has so consulted, with advisors, financial, legal or otherwise, of its choice with regard to the merits and risks of entering into and consummating the Transactions; and (c) has relied on its own business or financial experience or its own independent investigation, along with the representations, warranties, covenants and agreements made by TPRe in this Agreement and the information that TPRe has publicly filed with or furnished to the SEC, in determining to enter into and consummate the Transactions.

Section 4.10    Non-Reliance Except as set forth in this Agreement, no Preferred Shareholder has relied upon any representation, warranty, covenant or agreement, concerning the Transaction or the

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SiriusPoint Preference Shares, whether express or implied, of any kind or character, of TPRe or any of its affiliates or any of their respective directors, officers, employees, agents and controlling persons. In addition, no Preferred Shareholder has relied on TPRe to act in any advisory or fiduciary capacity in connection with the Seller’s decision to enter into this Agreement or any of the transactions contemplated by this Agreement.

Article 5.    Covenants and Agreements.

Section 5.01    Press Release and Announcements. Each of the Preferred Shareholders and TPRe shall consult with each other before issuing, and give each other reasonable opportunity to review and comment upon, any press release or other public statement with respect to the Transactions, and shall not (and shall not cause or permit their respective Subsidiaries or Representatives to) issue any such press release or make any such public statement prior to such consultation, except (i) as may be required by applicable Law, court process, or the rules and regulations of any national securities exchange or national securities quotation system, or (ii) to enforce its rights and remedies under this Agreement. Notwithstanding the foregoing, the Parties agree that the Preferred Shareholders shall have the reasonable opportunity to review and comment upon any filings with the SEC (including any Current Report on Form 8-K or any written communication made pursuant to Rule 425 under the Securities Act) to be made by TPRe with respect to the Transactions or the Potential Claims or that refer to the Preferred Shareholders between the date hereof and the Closing. TPRe and the Preferred Shareholders may make any oral or written public or internal announcements, releases or statements without complying with the foregoing requirements, if the substance of such announcements, releases or statements, was publicly or internally disclosed and previously subject to the foregoing requirements.

Section 5.02    Further Assurances. In case at any time any further action is necessary or desirable to carry out the purposes of this Agreement or the transactions contemplated hereby, each of the Parties will take such further action (including the execution and delivery of such further instruments and documents) as any other Party may reasonably request, all at the sole cost and expense of the requesting Party.

Section 5.03    Certain Covenants of TPRe. During the period from the date of this Agreement until the Closing or earlier termination of this Agreement, except as otherwise permitted by, or reasonably necessary to effectuate the transactions contemplated by, this Agreement, TPRe shall not and shall cause each of its Subsidiaries not to:

(a)    (i) issue or authorize the issuance of any equity securities in TPRe or any Subsidiary of TPRe, or securities convertible into, or exchangeable or exercisable for, any such equity securities, or any rights of any kind to acquire any such equity securities or such convertible or exchangeable securities, other than (A) equity securities that rank (or that, upon the issuance of the SiriusPoint Preference Shares, will rank) junior to, or on parity with, the SiriusPoint Preference Shares either as to the payment of dividends or as to the distribution of assets upon any liquidation, dissolution or winding-up of TPRe, (B) the “Merger Consideration Preference Shares” (as defined in the Merger Agreement) and (C) commitments to issue additional SiriusPoint Preference Shares to third parties at or following the Closing, or the issuance of additional SiriusPoint Preference Shares at any time following the date hereof, on a parity basis with the Preferred Shareholders and on terms no more favorable than those to be granted to the Preferred Shareholders in the SiriusPoint Certificate of Designation, or (ii) provide consent to the Company to issue or authorize the issuance of any equity securities in the Company or any Subsidiary of the Company, or securities convertible into, or exchangeable or exercisable for, any such equity securities, or any rights of any kind to acquire any such equity securities or such convertible or exchangeable securities;

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(b)    establish a record date for, declare, set aside or pay, or propose to declare, set aside or pay, any dividends on or make other distributions in respect of any of its share capital, options, warrants or other equity or voting interests (whether in cash, shares or property or any combination thereof), except for dividends or other distributions paid by a direct or indirect wholly owned Subsidiary to TPRe or its Subsidiaries;

(c)    other than the SiriusPoint Certificate of Designation or the “Parent Certificate of Designation” (as defined in the Merger Agreement), (A) amend the TPRe Organizational Documents or (B) amend in any material respect the comparable organizational documents of any of the Subsidiaries of TPRe, in the case of (A) and (B), in a manner that would reasonably be likely to prevent or to impede, interfere with, hinder or delay in any material respect the consummation of the Transactions or the rights of the SiriusPoint Preference Shares;

(d)    adopt a plan or agreement of complete or partial liquidation or dissolution, merger, amalgamation, consolidation, restructuring, recapitalization or other reorganization of TPRe or any of its Subsidiaries (other than dormant Subsidiaries or, with respect to any merger, amalgamation or consolidation, other than the Merger or among TPRe and any wholly owned Subsidiary of TPRe or among wholly owned Subsidiaries of TPRe); or

(e)    authorize any of, or commit or agree, in writing or otherwise, to take any of, the foregoing actions.

Section 5.04    Efforts. Upon the terms and subject to the conditions set forth in this Agreement, each of the Preferred Shareholders and TPRe shall, and shall cause its Subsidiaries to, use its commercially reasonable efforts to take, or cause to be taken, all actions and to do, or cause to be done, and to assist and cooperate with the other parties in doing, all things necessary, proper or advisable to fulfill all conditions applicable to such Party pursuant to this Agreement and to promptly consummate and make effective the transactions contemplated hereby, including executing and delivering any additional agreements, documents or instruments necessary, proper or advisable to consummate the transactions contemplated by, and to fully carry out the purposes and intent of, this Agreement.

Section 5.05    Registration Rights. TPRe and the Preferred Shareholders hereby make the agreements and covenants with respect to the marketing and registration of the SiriusPoint Preferred Shares that are set forth on Annex A to this Agreement, which is hereby incorporated into this Agreement by this reference.

Section 5.06    Stock Exchange Listing. TPRe shall use commercially reasonable efforts to cause the SiriusPoint Preference Shares to be issued in connection with the Exchange to be listed on the NYSE as soon as possible following the Closing, but in no event later than one hundred twenty (120) days following the Closing, at TPRe’s sole expense.

Section 5.07    Credit Rating. TPRe shall use reasonable best efforts to cause the SiriusPoint Preference Shares to be rated by each of S&P (at a rating of BB or higher) and Moody’s as soon as possible following the Closing and to cause a credit rating from S&P and Moody’s to be maintained for so long as any SiriusPoint Preference Shares remain outstanding, in each case at TPRe’s sole expense.

Section 5.08    Approvals. TPRe shall use reasonable best efforts to obtain the TPRe Board’s approval of this Agreement, the SiriusPoint Certificate of Designation and the Transactions (the “TPRe Board Approval”).

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Section 5.09    Bermuda Monetary Authority Review. Each of the Preferred Shareholders and TPRe agree that such Party will use reasonable best efforts to revise the SiriusPoint Certificate of Designation to the extent the Bermuda Monetary Authority requires changes to the SiriusPoint Preference Shares for the SiriusPoint Preference Shares to qualify as Tier 2 capital; provided that such changes do not materially adversely effect the economic position of the Preferred Shareholders or TPRe; and provided further, that each of the Parties will use reasonable best efforts (including by amending this Agreement) to ensure that any such revisions or changes will be done in a manner so as to cause each Party, to the extent reasonably practicable, to be in substantially the same position (including as to economic rights and priority) as the terms contemplated by this Agreement and the SiriusPoint Certificate of Designation as of the date hereof.

Article 6.    Conditions to the Obligations of the Parties at the Closing.

Section 6.01    Conditions to the Obligations of TPRe at the Closing. The obligation of TPRe to consummate the Transactions at the Closing is subject to the satisfaction on or prior to the Closing of each of the following conditions, each of which may be waived in writing by TPRe:

(a)    No Order. No Law or Order (whether temporary, preliminary or permanent) shall have been enacted, issued or enforced by any court or other Governmental Authority of competent jurisdiction that is in effect and that prevents or prohibits consummation of the Transactions.

(b)    Performance of Obligations and Agreement of the Preferred Shareholders. Each of the Preferred Shareholders shall have performed or complied in all material respects with the obligations and agreements required to be performed or complied with by it under this Agreement at or prior to the Closing, and TPRe shall have received a certificate signed on behalf of each of the Preferred Shareholders by an executive officer of each of the Preferred Shareholders to such effect.

(c)    Simultaneous Closing. The Merger and the other transactions contemplated by the Merger Agreement shall be consummated immediately prior to or concurrently with the Closing.

Section 6.02    Conditions to the Obligations of the Preferred Shareholders at the Closing. The obligations of the Preferred Shareholders to consummate the Transactions at the Closing is subject to the satisfaction on or prior to the Closing of each of the following conditions, each of which may be waived in writing by the Preferred Shareholders:

(a)    No Order. No Law or Order (whether temporary, preliminary or permanent) shall have been enacted, issued or enforced by any court or other Governmental Authority of competent jurisdiction that is in effect and that prevents or prohibits consummation of the Transactions.

(b)    Performance of Obligations and Agreement of TPRe. TPRe shall have performed or complied in all material respects with the obligations and agreements required to be performed or complied with by it under this Agreement at or prior to the Closing, and the Preferred Shareholders shall have received a certificate signed on behalf of TPRe by an executive officer of TPRe to such effect.

(c)    Simultaneous Closing. The Merger and the other transactions contemplated by the Merger Agreement shall be consummated immediately prior to or concurrently with the Closing.

Article 7.    Mutual Release and Additional Agreements.

Section 7.01    Mutual Release.

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(a)    In consideration of the covenants, agreements and undertakings of the Parties under this Agreement, effective only upon, and conditioned on, the consummation of the Transactions contemplated by the Closing, each Party, on behalf of itself and its respective present and former parents, subsidiaries, affiliates, officers, directors, shareholders, members, successors, and assigns (collectively, “Releasors”) hereby voluntarily, knowingly, fully and thereafter irrevocably releases, waives, and forever discharges the other Party and its respective present and former, direct and indirect, parents, subsidiaries, affiliates, employees, officers, directors, shareholders, members, agents, representatives, permitted successors, and permitted assigns (collectively, “Releasees”) of and from any and all actions, causes of action, suits, losses, liabilities, rights, debts, dues, sums of money, accounts, reckonings, obligations, costs, expenses, liens, bonds, bills, specialties, covenants, contracts, controversies, agreements, promises, variances, trespasses, damages, judgments, extents, executions, claims, and demands, of every kind and nature whatsoever, whether now known or unknown, foreseen or unforeseen, matured or unmatured, suspected or unsuspected, fixed or contingent, in law, admiralty, or equity (collectively, “Claims”), which any of such Releasors ever had, now have, or hereafter can, shall, or may have against any of such Releasees for, upon, or by reason of any matter, cause, or thing whatsoever from the beginning of time through the date of this Agreement arising out of or relating to directly or indirectly the Potential Claims or their ownership or rights under the Series B Preference Shares.

(b)    Each Releasor understands that it may later discover Claims or facts that may be different from, or in addition to, those that it or any other Releasor now knows or believes to exist regarding the subject matter of the release contained in this Article 7, and which, if known at the time of signing this Agreement, may have materially affected this Agreement and such Party’s decision to enter into it and grant the release contained in this Article 7. Nevertheless, the Releasors intend to fully, finally and forever settle and release all Claims that now exist, may exist, or previously existed, as set out in the release contained in this Article 7, whether known or unknown, foreseen or unforeseen, or suspected or unsuspected, and the release given herein is and will remain in effect as a complete release, notwithstanding the discovery or existence of such additional or different facts. The Releasors hereby waive any right or Claim that might arise as a result of such different or additional Claims or facts.

(c)    The release contained in this Article 7 shall not apply for the benefit of, and shall be null and void as to, any Releasee that makes any demand, brings any claim, or initiates any proceedings in any forum against any of the Preferred Shareholders or their affiliates arising out of or relating to directly or indirectly the Potential Claims or their ownership or rights under the Series B Preference Shares.

(d)    For the avoidance of doubt, this Section 7.01 and the conditional release of Claims contained herein shall be null and void, shall be deemed never to have become effective, and shall have no force and effect on any of the Releasors or any other party if the Closing does not occur in accordance with this Agreement.

Section 7.02    Additional Agreements.

(a)    Any statute of limitations, statute of repose and other time-related defense or claim, whether statutory, contractual or otherwise, whether under federal or state law, and whether at law, in equity or otherwise (including, but not limited to, the doctrines of waiver, laches, acquiescence, or estoppel), in any jurisdiction anywhere in the world, which are or may be applicable to the Potential Claims is hereby tolled for the duration of, and shall not run at any time during, the period beginning on the date of this Agreement and ending on the earlier of (i) the date when this Agreement is terminated pursuant to Section 9.02 and (ii) the consummation of the Transactions contemplated by the Closing (such period, the “Tolling Period”).

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(b)    The Parties agree not to assert directly or indirectly, plead, raise by defense or avoidance, or otherwise rely on any passage of time during the Tolling Period in asserting any defenses related to the Potential Claims.

(c)    During the Tolling Period, each Party agrees that it will not, and will cause its officers, directors, partners, employees, attorneys and other representatives not to, initiate or commence an action or proceeding against any other Party arising out of or relating in any way to the Potential Claims. The obligations in this Section 7.02(c) shall immediately cease and become null and void in the event that Sirius, any of its shareholders (other than any of the Preferred Shareholders), their affiliates, their lenders, or anyone acting on their behalf makes any demand, brings any claim, or initiates any proceedings in any forum against any of the Preferred Shareholders or their affiliates arising out of or relating to directly or indirectly the Potential Claims or their ownership or rights under the Series B Preference Shares.

(d)    The execution of this Agreement is not, and shall not operate as, and shall not be construed as, an admission of liability, wrongdoing, or responsibility by the Parties to any person or entity, and nothing herein shall prejudice or affect any other rights or liabilities of the Parties or be used to form the basis of any liability against any Party, nor shall it be asserted or construed to be a waiver of any Potential Claims.

(e)    Nothing in this Agreement shall be taken as an admission by any Party as to the applicability, running, expiration or non-expiration of any statute of limitations or similar rule of law or equity.

(f)    Nothing in this Agreement shall have the effect of reviving any claims that are otherwise barred by any statute of limitations or defense in law or equity relating to the passage of time prior to the date hereof and all time both prior to and after the period in which this Agreement is in effect shall be taken into account in determining when any claim has become or becomes barred by any statute of limitations or any defense in law or equity relating to the passage of time.

(g)    This Agreement may not be introduced into evidence in any action or proceeding, except to the extent necessary to enforce or effectuate the terms of this Agreement and to oppose the assertion of a time-related defense or claim.

Section 7.03    Confidentiality.

(a)    The Parties mutually agree that they shall keep strictly confidential, and shall not, directly or indirectly, disclose to any person or entity (other than their respective legal counsel and as permitted pursuant to Section 7.03(b) below) the Preferred Shareholders’ claims and allegations against the Company regarding the alleged redemption rights under the Series B Certificate of Designation and the facts and circumstances surrounding such claims and allegations, including, but not limited to, any and all facts or allegations concerning the alleged misconduct that the Preferred Shareholders contend the Company and the Company Board committed, as set forth in the redemption notices and related correspondence sent by the Preferred Shareholders to the Company and to the Company Board dated April 12, 2020 and April 13, 2020, and in letters from Kirkland & Ellis LLP to the Company Board dated March 30, 2020, May 16, 2020 and May 27, 2020 or otherwise. For the avoidance of doubt, this Section 7.03 and the confidentiality obligations contained herein shall not survive the termination of this Agreement pursuant to Section 9.02.

(b)    Nothing in this Agreement or any other agreement between the Parties or any other policies of the Company or any of its subsidiaries prohibits or restricts the Preferred Shareholders or the Preferred Shareholders’ attorneys from: (i) making any disclosure of relevant and necessary information or

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documents in any internal investigation, government investigation, action or proceeding as required by law or legal process, including with respect to possible violations of law, (ii) participating, cooperating, or testifying in any action, investigation, or proceeding with, or providing information to, any governmental agency or legislative body, any self-regulatory organization, and/or pursuant to the Sarbanes-Oxley Act or (iii) making any disclosure that is reasonably necessary to be disclosed to a potential acquirer in connection with a transfer of such Preferred Shareholder’s Series B Preference Shares or SiriusPoint Preferred Shares in accordance with this Agreement; provided that such potential acquirer agrees to keep such disclosure confidential.

Article 8.    Definitions. The following terms shall have the respective meanings set forth below throughout this Agreement:

“Affiliate” means, as to any Person, any other Person that, directly or indirectly, controls, or is controlled by, or is under common control with, such Person. For this purpose, “control” (including, with its correlative meanings, “controlled by” and “under common control with”) shall mean the possession, directly or indirectly, of the power to direct or cause the direction of management or policies of a Person, whether through the ownership of securities or partnership or other ownership interests, by contract or otherwise.

“Agreement” has the meaning set forth in the Preamble.

“Bain” has the meaning set forth in the Preamble.

“Bankruptcy and Equity Exception” has the meaning set forth in Section 3.03(a).

“Bermuda Companies Act” means the Companies Act 1981 of Bermuda.

“Business Day” means any day except a Saturday, a Sunday or other day on which the SEC or banks in the City of New York, New York or Hamilton, Bermuda are authorized or required by Law to be closed.

“Carlyle” has the meaning set forth in the Preamble.

“Centerbridge” has the meaning set forth in the Preamble.

“Claims” has the meaning set forth in Section 7.01(a).

“Closing” has the meaning set forth in Section 1.02(f).

“Closing Date” has the meaning set forth in Section 1.02(f).

“Company” has the meaning set forth in the Preamble.

“Company Common Shares” means the common shares, par value $0.01 per share, of the Company.

“Consent” means any consent, waiver, approval, license, Permit, order, non-objection, or authorization.

“Contract” means any loan or credit agreement, debenture, note, bond, mortgage, indenture, deed of trust, lease, sublease, license, contract or other binding agreement.

“Encumbrances” means, collectively, all Liens, agreements, voting trusts, proxies and other arrangements or restrictions of any kind whatsoever, but excluding any restrictions on transferability imposed by any securities Laws or, as applicable, the Shareholders Agreement.

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“Exchange” has the meaning set forth in Section 1.02(a).

“Exchange Amount” has the meaning set forth in Section 1.02(a).

“Exchange Shares” has the meaning set forth in Section 1.02(a).

“GAAP” means United States generally accepted accounting principles consistently applied, as in effect from time to time.

“Gallatin” has the meaning set forth in the Preamble.

“Governmental Authority” means any government, court, regulatory or administrative agency, commission or authority or other legislative, executive or judicial governmental entity, whether federal, national, provincial, state, local or multinational.

“Law” means any federal, national, provincial, state, local or multinational law, statute, code, rule or regulation.

“Lien” means any pledges, liens, charges, mortgages, encumbrances, leases, licenses, hypothecations or security interests of any kind or nature.

“Merger” has the meaning set forth in the Recitals.

“Merger Agreement” has the meaning set forth in the Recitals.

“Merger Sub” has the meaning set forth in the Recitals.

“Moody’s” means Moody’s Investors Service, Inc., and any successor thereto.

“NASDAQ” means the NASDAQ stock market.

“NYSE” means the New York Stock Exchange.

“Order” means any injunction, order, judgment, ruling, decree or writ, in each case, by or before any Governmental Authority.

“Party” has the meaning set forth in the Preamble.

“Permitted Liens” shall have the meaning given to such term in the Merger Agreement; provided that (a) all references therein to the “Effective Time” shall refer to the Closing (as defined in this Agreement) and (b) the term “Permitted Liens” shall also be deemed to include (i) Liens created by or through the actions of the Preferred Shareholders or any of their respective Affiliates, with respect to Liens applicable to TPRe or the Company and (ii) Liens created by or through the actions of TPRe, the Company or any of their respective Affiliates, with respect to Liens applicable to the Preferred Shareholders.

“Person” means an individual, a partnership, a corporation, a limited liability company, an association, a joint stock company, a trust, a joint venture, an unincorporated organization and a Governmental Authority.

“Potential Claims” has the meaning set forth in the Recitals.

“Preferred Shareholders” has the meaning set forth in the Preamble.

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“Registrar” means the Registrar of Companies in Bermuda.

“Releasees” has the meaning set forth in Section 7.01(a).

“Releasors” has the meaning set forth in Section 7.01(a).

“Representative” means, with respect to any Person, any director, officer, manager, member, partner (whether limited or general), principal, attorney, employee, agent, advisor, consultant, accountant, or any other Person acting in a representative capacity for such Person or, in the case of the Preferred Shareholders, any existing or potential financing source.

“S&P” means Standard & Poor’s Financial Services LLC, a subsidiary of S&P Global Inc. and any successor thereto.

“SEC” has the meaning set forth in Article 3.

“Securities Act” means the Securities Act of 1933 and the rules and regulations promulgated thereunder.

“Series B Certificate of Designation” has the meaning set forth in the Recitals.

“Series B Preference Shares” means the Series B preference shares, par value of $0.01 per share, of the Company.

“Shareholders Agreement” means that certain Shareholders Agreement, dated as of November 5, 2018, by and among the Company, CM Bermuda Ltd. and the Preferred Shareholders and/or Affiliates of the Preferred Shareholders.

“SiriusPoint” has the meaning set forth in the Recitals.

“SiriusPoint Certificate of Designation” has the meaning set forth in Section 1.02(a).

“SiriusPoint Preference Shares” has the meaning set forth in the Recitals.

“Subscription Agreements” has the meaning set forth in the Recitals.

“Subsidiary” when used with respect to any party, means any corporation, limited liability company, partnership, association, trust or other entity of which securities or other ownership interests representing more than 50% of the equity or more than 50% of the ordinary voting power (or, in the case of a partnership, more than 50% of the general partnership interests) are, as of such date, owned by such party or one or more Subsidiaries of such party or by such party and one or more Subsidiaries of such party.

“Tolling Period” has the meaning set forth in Section 7.02(a).

“TPRe” has the meaning set forth in the Preamble.

“TPRe Board” has the meaning set forth in the Recitals.

“TPRe Board Approval” has the meaning set forth in Section 5.08.

“TPRe Bye-Laws” means TPRe’s Amended and Restated Bye-Laws adopted July 31, 2018.

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“TPRe Charter” means the TPRe’s Memorandum of Association, as amended to the date of this Agreement.

“TPRe Material Adverse Effect” has the meaning given to the term “Parent Material Adverse Effect” in the Merger Agreement; provided that (a) all references therein to the “Transactions” shall refer to the Transactions (as defined in this Agreement) and (b) any manner set forth in the “Parent Disclosure Letter” (as defined in the Merger Agreement) shall only be excluded from the definition of “TPRe Material Adverse Effect” to the extent such matter is set forth on the Schedules delivered by TPRe to the Company and the Preferred Shareholders in connection with this Agreement.

“TPRe Organizational Documents” means the TPRe Charter and the TPRe Bye-Laws.

“TPRe SEC Documents” has the meaning set forth in Article 3.

“Transaction Agreements” means this Agreement, the SiriusPoint Certificate of Designation, and the various agreements, certificates, instruments and other documents contemplated thereby and each other agreement, certificate, instrument or other document contemplated by this Agreement.

“Transactions” has the meaning set forth in Section 1.02(f).

Article 9.    Miscellaneous.

Section 9.01    No Survival of Representations or Warranties. None of the representations or warranties in this Agreement or in any instrument delivered pursuant to this Agreement shall survive the Closing.

Section 9.02    Termination. In the event that (a)(i) the Merger Agreement is terminated in accordance with its terms without the Merger being consummated, (ii) the Merger has not been consummated by the Walk-Away Date (as defined in the Merger Agreement), including any extension of the Walk-Away Date pursuant to the Merger Agreement as may be agreed by the parties to the Merger Agreement or (iii) TPRe fails to provide the Preferred Shareholders with reasonably acceptable evidence of the TPRe Board Approval by September 11, 2020, this Agreement shall automatically terminate, or (b) the Merger has not been consummated on or prior to August 6, 2021, the Preferred Shareholders shall have the option to terminate this Agreement, and in any such case, if so terminated, this Agreement shall forthwith become null and void (other than Section 5.01, Section 7.02(b) and this Article 9, all of which shall survive termination of this Agreement), and there shall be no liability on the part of TPRe, the Preferred Shareholders or their respective directors, officers and Affiliates, except (x) as liability may exist pursuant to the provisions specified in the immediately preceding parenthetical that survive such termination and (y) that no such termination shall relieve any party for liability for fraud on the part of such party or any willful and material breach by such party of any representation, warranty, obligation or agreement set forth in this Agreement. For the avoidance of doubt, following any such termination of this Agreement, (A) the Preferred Shareholders shall continue to hold the Series B Preference Shares, (B) the Series B Preference Shares shall continue to be governed by the Series B Certificate of Designation and (C) as stated in Section 7.01(d), Section 7.01 and the conditional release of Claims contained therein shall be null and void, shall be deemed never to have become effective, and shall have no force and effect on any of the Releasors or any other party.

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Section 9.03    Preferred Shareholder Consents. Each of the Preferred Shareholders agrees and consents to the termination of the Shareholders Agreement upon the Closing.

Section 9.04    Fees and Expenses. Except as otherwise provided herein, each Party hereto shall pay all of its own costs, fees and expenses incurred by such Party in connection with this Agreement and the consummation (or the preparation for the consummation) of the Transactions. If any legal action or other proceeding relating to this Agreement, the other Transaction Agreements, the Transactions or the enforcement of any provision of this Agreement or the other Transaction Agreements is brought against any Party, the prevailing Party in such action or proceeding shall be entitled to recover all reasonable expenses relating thereto (including attorneys’ fees and expenses) from the Party against which such action or proceeding is brought in addition to any other relief to which such prevailing Party may be entitled.

Section 9.05    Remedies. Each of the Parties acknowledges and agrees that the other Parties would be damaged irreparably in the event any of the provisions of this Agreement are not performed in accordance with their specific terms or otherwise are breached and money damages would not be an adequate remedy. Accordingly, in addition to the other remedies available to the Parties, each Party agrees that the other Parties shall be entitled to an injunction or injunctions to prevent breaches of the provisions of this Agreement and to enforce specifically this Agreement and the terms and provisions hereof in any action instituted in any court of the United States or any state thereof having jurisdiction over the Parties and the matter.

Section 9.06    Waivers and Amendments. This Agreement may be amended, or any provision of this Agreement may be waived; provided that (a) any such amendment or waiver shall be binding upon any Preferred Shareholder only if set forth in a writing executed by such Preferred Shareholder and referring specifically to the provision alleged to have been amended or waived and (b) any such amendment or waiver shall be binding upon TPRe only if set forth in a writing executed by TPRe and referring specifically to the provision alleged to have been amended or waived. No course of dealing between or among the Parties shall be deemed effective to modify, amend or discharge any part of this Agreement or any rights or obligations of any Party under or by reason of this Agreement.

Section 9.07    Successors and Assigns. This Agreement and all of the covenants and agreements contained herein and the rights, interests or obligations hereunder, by or on behalf of any of the Parties, shall bind and inure to the benefit of the respective successors and assigns of the Parties whether so expressed or not, except that neither this Agreement nor any of the covenants and agreements herein or rights, interests or obligations hereunder may be assigned or delegated by any of the Parties, without the prior written consent of each of the other Parties; provided, that any Preferred Shareholder may assign its rights and obligations under this Agreement (or a relevant portion of such rights) to any Person in connection with a transfer of all or any portion of such Preferred Shareholder’s Series B Preference Shares, or such Preferred Shareholder’s SiriusPoint Preferred Shares, to such Person.

Section 9.08    Severability. Whenever possible, each provision of this Agreement shall be interpreted in such manner as to be effective and valid under applicable Law, but if any provision of this Agreement or the application of any such provision to any Person or circumstance shall be held to be prohibited by, illegal or unenforceable under applicable Law in any respect by a court of competent jurisdiction, such provision shall be ineffective only in the jurisdiction where so held and only to the extent of such prohibition or illegality or unenforceability, without invalidating the remainder of such provision or the remaining provisions of this Agreement.

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Section 9.09    Counterparts. This Agreement may be executed in counterparts, which collectively shall be deemed an original and which, taken together, shall constitute one and the same instrument. Electronic or facsimile copies of counterparts of this Agreement (including in .pdf format) shall have the full force and effect as an original.

Section 9.10    Descriptive Headings; Interpretation. The headings and captions used in this Agreement and the table of contents to this Agreement are for reference purposes only and shall not affect in any way the meaning or interpretation of this Agreement. Any capitalized terms used in any Schedule, Annex or Exhibit attached hereto and not otherwise defined therein shall have the meanings set forth in this Agreement. All references to statutes and related regulations shall include all amendments of the same and any successor or replacement statutes and regulations. References to “$” shall mean United States dollars. Words using the singular or plural number also shall include the plural or singular number, respectively. References to “hereof,” “herein,” “hereby” and similar terms shall refer to this entire Agreement (including the Schedules, Annexes and Exhibits hereto). References to any Person shall be deemed to mean and include the successors and permitted assigns of such Person (or, in the case of a Governmental Authority, Persons succeeding to the relevant functions of such Person). The term “or” shall not be exclusive. The use of the word “including” herein shall mean “including without limitation.” The Parties intend that each representation, warranty and covenant contained herein shall have independent significance. If any Party has breached any representation, warranty or covenant contained herein in any respect, the fact that there exists another representation, warranty or covenant relating to the same subject matter (regardless of the relative levels of specificity) which the Party has not breached shall not detract from or mitigate the fact that the Party is in breach of the first representation, warranty or covenant. Any reference to the masculine, feminine or neuter gender shall be deemed to include any gender or all three as appropriate. With respect to the determination of any period of time, unless otherwise set forth in this Agreement, the word “from” means “from and including” and the word “to” means “to but excluding” and if the last day of such period is a non-Business Day, the period in question will end at the end of the next succeeding Business Day.

Section 9.11    Entire Agreement. This Agreement and the Exhibits, Annexes and Schedules hereto, taken together with the other Transaction Agreements, the Shareholders Agreement, the Expense Reimbursement Agreement and the Series B Certificate of Designation, contain the entire agreement and understanding between the Parties with respect to the subject matter hereof and supersede all prior agreements and understandings, whether written or oral, relating to such subject matter in any way.

Section 9.12    No Third Party Beneficiaries. This Agreement is for the sole benefit of the Parties, and each of their permitted successors and assigns, and nothing herein expressed or implied shall give or be construed to give any Person, other than the Parties and such permitted successors and assigns, any legal or equitable rights hereunder.

Section 9.13    Governing Law; Jurisdiction; WAIVER OF JURY TRIAL.

(a)    This Agreement, and all claims or causes of action (whether at law or in equity, in contract or in tort) that may be based upon, arise out of or relate to this Agreement, or the negotiation, execution or performance hereof, or the transactions contemplated in this Agreement, shall be governed by and construed in accordance with the laws of the State of New York.

(b)    Without limiting any Party from enforcing any judgment or seeking specific performance as an interim measure, the Parties agree that jurisdiction and venue in any suit, action, or proceeding brought by any Party pursuant to this Agreement or the transactions contemplated hereby shall properly and exclusively lie in the courts of the State of New York or the United States District Court for the

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Southern District of New York. Each Party also agrees not to bring any suit, action or proceeding, arising out of or relating to this agreement or the transactions contemplated hereby in any other court (other than upon the appeal of any judgment, decision or action of any such court located in New York or, as applicable, any federal appellate court that includes the State of New York within its jurisdiction). By execution and delivery of this agreement, each Party irrevocably submits to the jurisdiction of such courts for itself and in respect of its property with respect to such suit, action or proceeding. The Parties irrevocably agree that venue would be proper in such court, and hereby waive any objection that any such court is an improper or inconvenient forum for the resolution of such suit, action or proceeding. Each of the Parties further irrevocably and unconditionally consents to service of process in the manner provided for notices in Section 9.14 of this Agreement. Nothing in this Agreement will affect the right of any Party to this Agreement to serve process in any other manner permitted by Law.

(c)    THE PARTIES EACH HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY LAW, ANY RIGHT TO TRIAL BY JURY OF ANY CLAIM, DEMAND, ACTION, OR CAUSE OF ACTION (I) ARISING UNDER THIS AGREEMENT OR ANY TRANSACTION AGREEMENT OR (II) IN ANY WAY CONNECTED WITH OR RELATED OR INCIDENTAL TO THE DEALINGS OF THE PARTIES IN RESPECT OF THIS AGREEMENT, ANY TRANSACTION AGREEMENT OR ANY OF THE TRANSACTIONS RELATED HERETO, IN EACH CASE WHETHER NOW EXISTING OR HEREAFTER ARISING, AND WHETHER IN CONTRACT, TORT, EQUITY, OR OTHERWISE. THE PARTIES TO THIS AGREEMENT EACH HEREBY AGREES AND CONSENTS THAT ANY SUCH CLAIM, DEMAND, ACTION, OR CAUSE OF ACTION SHALL BE DECIDED BY COURT TRIAL WITHOUT A JURY AND THAT THE PARTIES TO THIS AGREEMENT MAY FILE AN ORIGINAL COUNTERPART OF A COPY OF THIS AGREEMENT WITH ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF THE PARTIES TO THE IRREVOCABLE WAIVER OF THEIR RIGHT TO TRIAL BY JURY.

Section 9.14    Notices. All notices, demands or other communications to be given or delivered under or by reason of the provisions of this Agreement shall be in writing and shall be deemed to have been given only (a) when delivered in person or sent by email, (b) one (1) Business Day after being sent to the recipient by reputable overnight courier service (charges prepaid), or (c) five (5) Business Days after being mailed to the recipient by certified or registered mail (return receipt requested and postage prepaid). Such notices, demands and communications shall, unless another address is specified in writing pursuant to the provisions hereof, be sent to the address indicated below:

Notices to TPRe (or, after the closing of the Merger, the Company):

Third Point Reinsurance Ltd.

Point House

3 Waterloo Lane

Pembroke HM 08 Bermuda

Attention:    Janice R. Weidenborner

Email:        Janice.Weidenborner@thirdpointre.com

with a copy (which shall not constitute notice) to:

Debevoise & Plimpton LLP

919 Third Avenue

New York, New York 10022

Attention:    Nicholas F. Potter

Email:        nfpotter@debevoise.com

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Notices to the Preferred Shareholders:

Bain Capital Special Situations Asia, L.P.

c/o Bain Capital

200 Clarendon Street

Boston, Massachusetts 02116

Attention: General Counsel

CCOF Master, L.P.

c/o The Carlyle Group

520 Madison Avenue

New York, New York 10022

Attention: General Counsel

Centerbridge Credit Partners Master, LP

Centerbridge Special Credit Partners III, LP

c/o Centerbridge Partners

375 Park Avenue

New York, New York 10152

Attention: General Counsel

GPC Partners Investments (Canis) LP

c/o Gallatin Point Capital

660 Steamboat Road, First Floor

Greenwich, Connecticut 06830

Attention: General Counsel

with a copy (which shall not constitute notice) to:

Kirkland & Ellis LLP

601 Lexington Avenue

New York, New York

Attention:    Rajab S. Abbassi, P.C.; David L. Perechocky

Email:        rajab.abbassi@kirkland.com; david.perechocky@kirkland.com     

Without limiting the foregoing, any party hereto may give any notice, request, instruction, demand, document or other communication hereunder using any other means (including personal delivery, expedited courier, messenger service, ordinary mail, or electronic mail), but no such notice, request, instruction, demand, document or other communication shall be deemed to have been duly given unless and until it actually is received by the party for whom it is intended.

Section 9.15    No Strict Construction. The Parties have participated jointly in the negotiation and drafting of this Agreement. In the event an ambiguity or question of intent or interpretation arises, this Agreement shall be construed as if drafted jointly by the Parties, and no presumption or burden of proof shall arise favoring or disfavoring any Party by virtue of the authorship of any of the provisions of this Agreement.

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IN WITNESS WHEREOF, the Parties have executed or caused to be executed on their behalf this Transaction Agreement on the date first written above.

TPRE

THIRD POINT REINSURANCE LTD.

By: /s/ Sid Sankaran_____

Name: Sid Sankaran_______

Title: Chairman___________

Signature Page to Transaction Agreement

i

IN WITNESS WHEREOF, the Parties have executed or caused to be executed on their behalf this Transaction Agreement on the date first written above.

PREFERRED SHAREHOLDERS

BAIN

Bain Capital Special Situations Asia, L.P.

By: Bain Capital Special Situations Asia

Investors, LLC, its general partner

By: Bain Capital Credit Member II, Ltd., its

manager

By: /s/ Andrew S. Viens_____

Name: Andrew S. Viens_______

Its: Managing Director______

 

CARLYLE

CCOF Master, L.P.

By: CCOF General Partner, L.P., its general

partner

By: CCOF L.L.C., its general partner

By: /s/ Alexander Popov______

Name: Alexander Popov______

Its: Managing Director_______

 

CENTERBRIDGE

Centerbridge Credit Partners Master, LP

By: Centerbridge Credit Partners Offshore

General Partner, L.P.

By: Centerbridge Credit Cayman GP, Ltd., its

general partner

By: /s/ Susanne V. Clark____

Name: Susanne V. Clark____

Its: Authorized Signatory___

Signature Page to Transaction Agreement

ii

Centerbridge Special Credit Partners III, LP

By: Centerbridge Special Credit Partners General

Partner III, L.P.

By: CSCP III Cayman GP, Ltd., its general

partner

By: /s/ Susanne V. Clark____

Name: Susanne V. Clark____

Its: Authorized Signatory___

 

GALLATIN

GPC Partners Investments (Canis) LP

By: GPC Partners GP LLC, its general partner

By: Gallatin Point Capital LLC, its sole member

By: /s/ Matthew Botein________

Name: __Matthew Botein______

Its: Managing Partner_________

Signature Page to Transaction Agreement 

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Schedule I

Preference Shares and Ownership Percentages

I	II	III
Preferred Shareholder	Series B Preference Shares Outstanding	Preferred Shareholder Pro Rata Ownership Percentage
Bain Capital Special Situations Asia, L.P.	1,451,423	12.1951%
CCOF Master, L.P.	3,483,416	29.2683%
Centerbridge Credit Partners Master, LP	2,673,870	22.4663%
Centerbridge Special Credit Partners III, LP	809,546	6.8020%
GPC Partners Investments (Canis) LP	3,483,415	29.2683%
TOTAL	11,901,670	100%

1006165296v6

ANNEX A

REGISTRATION RIGHTS

Note: Certain capitalized terms used in this Annex are defined in Section 10 of this Annex. Capitalized terms used but not defined herein have the meanings set forth in the Agreement. Unless otherwise noted, all references in this Annex to a “Section” refer to a Section of this Annex.

Section 1.    Shelf Registrations.

(a)    Promptly following the Closing Date, the Issuer shall use its commercially reasonable efforts to prepare a registration statement under the Securities Act (the “Shelf Registration Statement”) for a registration pursuant to Rule 415 under the Securities Act on Form S-3 (a “Shelf Registration”) and, if the Issuer is a WKSI at the time of filing the Shelf Registration Statement, such Shelf Registration shall be an automatic shelf registration statement (as defined in Rule 405 under the Securities Act) (an “Automatic Shelf Registration Statement”) with respect to all of the Registrable Securities (or such other number of Registrable Securities specified in writing by the Holder thereof) to enable such Shelf Registration Statement to be filed with the Commission as soon as possible following the Closing Date, but in no event later than 120 days following the Closing Date. The Issuer will notify each holder of Registrable Securities within two Business Days of the filing of such Shelf Registration Statement.

(b)    In the event that a Shelf Registration Statement is effective, any holder of Registrable Securities covered by such Shelf Registration Statement shall have the right at any time or from time to time to elect to sell pursuant to an offering (including an underwritten offering) Registrable Securities available for sale pursuant to such registration statement (“Shelf Registrable Securities”), so long as the Shelf Registration Statement remains in effect, and the Issuer shall pay all Registration Expenses in connection therewith. Any holder of Registrable Securities shall make such election by delivering to the Issuer a written notice (a “Shelf Offering Notice”) with respect to such offering specifying the number of Shelf Registrable Securities that such holder desires to sell pursuant to such offering (the “Shelf Offering”); provided that a Shelf Offering Notice may only be made if the sale of Registrable Securities requested to be sold are reasonably expected to result in aggregate gross cash proceeds in excess of $25,000,000 (unless any such holder of Registrable Securities is proposing to sell all of its remaining Registrable Securities). As promptly as practicable, but no later than two Business Days after receipt of a Shelf Offering Notice, the Issuer shall give written notice of such Shelf Offering Notice to all other holders of Shelf Registrable Securities. The Issuer, subject to Section 1(e) and Section 7 hereof, shall include in such Shelf Offering the Shelf Registrable Securities of any other holder of Shelf Registrable Securities that shall have made a written request to the Issuer for inclusion in such Shelf Offering (which request shall specify the maximum number of Shelf Registrable Securities intended to be disposed of by such holder) within five Business Days after the receipt of the Shelf Offering Notice. The Issuer shall, as expeditiously as possible (and in any event within 10 Business Days after the receipt of a Shelf Offering Notice), but subject to Section 1(f) hereof, use its reasonable best efforts to facilitate such Shelf Offering. Each Holder agrees that such Holder shall treat as

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confidential the Shelf Offering Notice and shall not disclose or use the information contained in the Issuer’s notice regarding the Shelf Offering Notice without the prior written consent of the Issuer and the Holders of Registrable Securities delivering such Shelf Offering Notice until such time as the information contained therein is or becomes available to the public generally, other than as a result of disclosure by the Holder in breach of the terms of the Agreement.

(c)    If any holder of the Registrable Securities wishes to engage in an underwritten block trade off of a Shelf Registration Statement (either through filing an Automatic Shelf Registration Statement or through a take-down from an already existing Shelf Registration Statement), then notwithstanding the time periods set forth in Section 1(b), such holder shall notify the Issuer of the block trade Shelf Offering not less than two Business Days prior to the day such offering is to commence. The Issuer shall promptly notify other holders of Registrable Securities of such block trade Shelf Offering and such other holders of Registrable Securities must elect whether or not to participate by the next Business Day (i.e., one Business Day prior to the day such offering is to commence) (unless a longer period is agreed to by the holders of a majority of the Registrable Securities wishing to engage in the underwritten block trade) and the Issuer shall as expeditiously as possible use its reasonable best efforts to facilitate such offering (which may close as early as two Business Days after the date it commences).

(d)    The Issuer shall, at the request of any holder of the Registrable Securities covered by a Shelf Registration Statement, file any prospectus supplement or any post-effective amendments and otherwise take any action necessary to include therein all disclosure and language deemed necessary or advisable by any holder of the Registrable Securities to effect such Shelf Offering.

(e)    Priority on Shelf Offerings. If a Shelf Offering is an underwritten offering and the managing underwriters advise the Issuer in writing that in their opinion the number of Registrable Securities and, if permitted hereunder, other securities requested to be included in such offering exceeds the number of Registrable Securities and other securities, if any, which can be sold therein without adversely affecting the marketability, proposed offering price, timing or method of distribution of the offering, the Issuer shall include in such offering prior to the inclusion of any securities which are not Registrable Securities the number of Registrable Securities requested to be included which, in the opinion of such underwriters, can be sold, without any such adverse effect, pro rata among the respective holders thereof on the basis of the amount of Registrable Securities owned by each such holder.

(f)    Restrictions on Shelf Offerings.

(i)    The Issuer may postpone, for up to 90 days from the date of the request (the “Suspension Period”), the filing or the effectiveness of a registration statement for a Shelf Registration or suspend the use of a prospectus that is part of a Shelf Registration Statement (and therefore suspend sales of the Shelf Registrable Securities) by providing written notice to the holders of Registrable Securities if (A) the Issuer’s board of directors determines in its

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reasonable good faith judgment that the offer or sale of Registrable Securities would reasonably be expected to have a material adverse effect on any proposal or plan by the Issuer or any Subsidiary to engage in any material acquisition of assets or stock (other than in the ordinary course of business) or any material merger, consolidation, tender offer, recapitalization, reorganization or other transaction involving the Issuer, (B) upon advice of counsel, the sale of Registrable Securities pursuant to the registration statement would require disclosure of material non-public information not otherwise required to be disclosed under applicable law or (C) (x) the Issuer has a bona fide business purpose for preserving the confidentiality of such transaction or (y) disclosure would have a material adverse effect on the Issuer or the Issuer’s ability to consummate such transaction or (z) such transaction renders the Issuer unable to comply with Commission requirements, in each case under circumstances that would make it impractical or inadvisable to cause the Shelf Registration Statement (or such filings) to become effective or to promptly amend or supplement the Shelf Registration Statement on a post effective basis, as applicable. The Issuer may delay or suspend the effectiveness of a Shelf Registration or Shelf Offering pursuant to this Section 1(f)(i) only once in any twelve-month period; provided that, for the avoidance of doubt, the Issuer may in any event delay or suspend the effectiveness of Shelf Registration or Shelf Offering in the case of an event described under Section 4(a)(vi) to enable it to comply with its obligations set forth in Section 4(a)(vi).

(ii)    In the case of an event that causes the Issuer to suspend the use of a Shelf Registration Statement as set forth in Section 1(f)(i) or pursuant to Section 4(a)(vi) (a “Suspension Event”), the Issuer shall give a notice to the holders of Registrable Securities registered pursuant to such Shelf Registration Statement (a “Suspension Notice”) to suspend sales of the Registrable Securities and such notice shall state generally the basis for the notice and that such suspension shall continue only for so long as the Suspension Event or its effect is continuing. A holder of Registrable Securities shall not effect any sales of its Registrable Securities pursuant to such Shelf Registration Statement (or such filings) at any time after it has received a Suspension Notice from the Issuer and prior to receipt of an End of Suspension Notice (as defined below). Each holder of Registrable Securities agrees that it shall treat as confidential the receipt of the Suspension Notice and shall not disclose or use the information contained in such Suspension Notice without the prior written consent of the Issuer until such time as the information contained therein is or becomes available to the public generally, other than as a result of disclosure by such holder of Registrable Securities in breach of the terms of the Agreement. A holder of Registrable Securities may recommence effecting sales of the Registrable Securities pursuant to the Shelf Registration Statement (or such filings) following further written notice to such effect (an “End of Suspension Notice”) from the Issuer, which End of Suspension Notice shall be given by the Issuer to the holders and to the holders’ counsel, if any, promptly following the conclusion of any Suspension Event.

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(iii)    Notwithstanding any provision herein to the contrary, if the Issuer shall give a Suspension Notice with respect to any Shelf Registration Statement pursuant to this Section 1(f), the Issuer agrees that it shall extend the period of time during which such Shelf Registration Statement shall be maintained effective pursuant to this Annex by the number of days during the period from the date of receipt by the holders of the Suspension Notice to and including the date of receipt by the holders of the End of Suspension Notice and provide copies of the supplemented or amended prospectus necessary to resume sales, with respect to each Suspension Event.

(iv)    the Company shall not be obligated to file any Shelf Registration Statement, participate in the launch of or effect any Shelf Offering within the period commencing on the last day of any quarter or year and ending two days following the Company’s earnings release for any fiscal quarter or fiscal year.

(g)    Selection of Underwriters. If any Shelf Offering is an underwritten offering, the holders of a majority of the Registrable Securities participating in such underwritten offering shall have the right to select the investment banker(s) and manager(s) to administer the offering relating to such Shelf Offering.

(h)    Other Registration Rights. Except as provided in the Agreement or pursuant to the Merger Agreement, the Issuer shall not grant any registration rights to any Persons with respect to any preference shares of the Issuer or any Subsidiary, or any securities convertible or exchangeable into or exercisable for such securities, without the prior written consent of the holders of a majority of the Registrable Securities (such consent not to be unreasonably withheld or delayed); provided that the Issuer may grant, with respect to preference shares of the Issuer or any Subsidiary (i) rights to other Persons to participate in Piggyback Registrations so long as such rights are not senior to the rights of the holders of Registrable Securities with respect to such Piggyback Registrations as set forth in Section 2(c), (ii) rights to Shelf Registrations and Shelf Offerings so long as such rights are not senior to the rights of the holders of Registrable Securities as set forth in this Section 1 and (iii) such other registration rights that are no more favorable to such other Person in any respect than the rights set forth in this Annex.

(i)    Revocation of Shelf Offering Notice. At any time prior to the effective date of the registration statement relating to a Shelf Registration or the “pricing” of any offering relating to a Shelf Offering Notice, the holders of Registrable Securities that provided the applicable Shelf Offering Notice may revoke such Shelf Offering Notice on behalf of all holders of Registrable Securities participating in such Shelf Offering without liability to such holders of Registrable Securities, in each case by providing written notice to the Issuer.

Section 2.    Piggyback Registrations.

(a)    Right to Piggyback. Whenever the Issuer proposes to register any of its preference shares, or securities convertible into, or exchangeable or exercisable for, preference shares, under the Securities Act for its own account (other than in connection with registrations on

4

Form S 4 or S 8 promulgated by the Commission or any successor or similar forms) (a “Piggyback Registration”), the Issuer shall give prompt written notice (in any event at least 5 Business Days before the anticipated filing date of the applicable registration statement or preliminary prospectus supplement, as the case may be) to all holders of Registrable Securities of its intention to effect such Piggyback Registration and, subject to the terms of Section 2(c), shall include in such Piggyback Registration (and in all related registrations or qualifications under blue sky laws and in any related underwriting) all Registrable Securities with respect to which the Issuer has received written requests for inclusion therein within 5 Business Days after delivery of the Issuer’s notice.

(b)    Piggyback Expenses. The Registration Expenses of the holders of Registrable Securities shall be paid by the Issuer in all Piggyback Registrations, whether or not any such registration became effective.

(c)    Priority on Primary Registrations. If a Piggyback Registration is an underwritten primary registration on behalf of the Issuer, and the managing underwriters advise the Issuer in writing that in their opinion the number of securities requested to be included in such registration exceeds the number which can be sold in such offering without adversely affecting the marketability, proposed offering price, timing or method of distribution of the offering, the Issuer shall include in such registration (i) first, the securities the Issuer proposes to sell and, (ii) second, the Registrable Securities requested to be included in such registration which, in the opinion of the underwriters, can be sold without any such adverse effect, pro rata among the holders of such Registrable Securities and other securities requested to be included in such registration on the basis of the number of shares owned by each such holder.

(d)    Selection of Underwriters. If any Piggyback Registration is an underwritten offering, the selection of investment banker(s) and manager(s) for the offering will be determined by the Issuer in its sole discretion.

Section 3.    Holdback Agreements.

(a)    Holders of Registrable Securities. In connection with any underwritten Public Offering, each holder of Registrable Securities shall enter into lock-up agreements with the managing underwriter(s) that provide for the following unless the underwriters managing such underwritten Public Offering otherwise agree in writing: such holder shall not (A) offer, sell, contract to sell, pledge or otherwise dispose of (including sales pursuant to Rule 144), directly or indirectly, any Capital Stock of the Issuer (including Capital Stock of the Issuer that may be deemed to be owned beneficially by such holder in accordance with the rules and regulations of the Commission) (collectively, “Securities”) or any securities, options or rights convertible into or exchangeable or exercisable for Securities (collectively, “Other Securities”), (B) enter into a transaction which would have the same effect as described in clause (A) above, (C) enter into any swap, hedge or other arrangement that transfers, in whole or in part, any of the economic consequences or ownership of any Securities, whether such transaction is to be settled by delivery of such Securities, in cash or otherwise (each of (A), (B) and (C) above, a “Sale Transaction”) or (D) publicly disclose the intention to enter into any Sale Transaction, commencing on the earlier of the date on which the Issuer gives notice to the holders of Registrable Securities of the circulation of a preliminary or final prospectus (or prospectus supplement) for such Public Offering or the “pricing” of such offering and continuing to the date that is 90 days following the date of the final

5

prospectus for such Public Offering (such period, or such shorter period as agreed to by the managing underwriter(s), a “Holdback Period”), in each case with such modifications and exceptions as may be approved by the Issuer and the holders of a majority of the Registrable Securities. In addition, upon request by the managing underwriter(s), each holder shall enter into customary holdback agreements consistent with the terms herein.

(b)    The Issuer. The Issuer (i) will not file any registration statement for a sale or distribution by the Issuer, one of its Subsidiaries and/or shareholders to the public of Securities or Other Securities pursuant to an offering registered under the Securities Act or cause any such registration statement to become effective, or effect any public sale or distribution of its Securities or Other Securities during any Holdback Period (other than as part of such underwritten offering, or a registration on Form S-4 or Form S-8 or any successor or similar form) and (ii) will cause each of its directors and executive officers to agree not to effect any Sale Transaction during any Holdback Period, except as part of such underwritten offering (if otherwise permitted), unless approved in writing by the underwriters managing the underwritten offering and to enter into any lock-up, holdback or similar agreements requested by the underwriter(s) managing such offering, in each case with such modifications and exceptions as may be approved by the Issuer and the holders of a majority of the Registrable Securities.

Section 4.    Marketing Cooperation and Registration Procedures.

(a)    From and after the date hereof, whenever the holders of Registrable Securities have initiated a Shelf Offering, or otherwise upon the reasonable request of a holder of Registrable Securities, the Issuer shall use its reasonable best efforts to effect the registration and the sale of such Registrable Securities in accordance with the intended method of disposition thereof, and to provide all reasonable cooperation as the holders of Registrable Securities may reasonably request to assist the holders of Registrable Securities in the marketing, resale or disposition of the Registrable Securities, including to, as expeditiously as possible:

(i)    in accordance with the Securities Act and all applicable rules and regulations promulgated thereunder, (A) prepare and file with the Commission a registration statement, and all amendments and supplements thereto and related prospectuses, with respect to such Registrable Securities and use its commercially reasonable efforts to cause such registration statement to be declared effective or otherwise become effective as soon as reasonably practicable on or following the date such registration statement is filed with the Commission but, in any event, no later than the Effectiveness Deadline (provided that not less than five Business Days before filing a registration statement or prospectus or any amendments or supplements thereto, the Issuer shall furnish to the counsel selected by the holders of a majority of the Registrable Securities covered by such registration statement copies of all such documents proposed to be filed, which documents shall be subject to the review and comment of such counsel) and (B) respond as promptly as reasonably practicable to any comments received from the Commission and request acceleration of effectiveness as promptly as reasonably practicable after it learns that the Commission will not review the registration statement or after it has satisfied comments received from the Commission;

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(ii)    notify each holder of Registrable Securities of (A) the issuance by the Commission of any stop order suspending the effectiveness of any registration statement or the initiation of any proceedings for that purpose, (B) the receipt by the Issuer or its counsel of any notification with respect to the suspension of the qualification of the Registrable Securities for sale in any jurisdiction or the initiation or threatening of any proceeding for such purpose, and (C) the effectiveness of each registration statement filed hereunder;

(iii)    prepare and file with the Commission such amendments and supplements to such registration statement and the prospectus used in connection therewith as may be necessary to keep such registration statement effective for a period ending when all of the securities covered by such registration statement have been disposed of in accordance with the intended methods of distribution by the sellers thereof set forth in such registration statement (but not in any event before the expiration of any longer period required under the Securities Act or, if such registration statement relates to an underwritten Public Offering, such longer period as in the opinion of counsel for the underwriters a prospectus is required by law to be delivered in connection with the sale of Registrable Securities by an underwriter or dealer) and comply with the provisions of the Securities Act with respect to the disposition of all securities covered by such registration statement during such period in accordance with the intended methods of disposition by the sellers thereof set forth in such registration statement;

(iv)    furnish to each seller of Registrable Securities thereunder such number of copies of such registration statement, each amendment and supplement thereto, the prospectus included in such registration statement (including each preliminary prospectus), each Free Writing Prospectus and such other documents as such seller may reasonably request in order to facilitate the disposition of the Registrable Securities owned by such seller;

(v)    use its commercially reasonable efforts to register or qualify such Registrable Securities under such other securities or blue sky laws of such jurisdictions as any seller reasonably requests and do any and all other acts and things which may be reasonably necessary or advisable to enable such seller to consummate the disposition in such jurisdictions of the Registrable Securities owned by such seller (provided that the Issuer shall not be required to (A) qualify generally to do business in any jurisdiction where it would not otherwise be required to qualify but for this subparagraph, (B) consent to general service of process in any such jurisdiction) or (C) subject itself to taxation in any jurisdiction where it is not then so subject;

(vi)    notify each seller of such Registrable Securities (A) promptly after it receives notice thereof, of the date and time when such registration statement and each post-effective amendment thereto has become effective or a prospectus or supplement to any prospectus relating to a registration statement has been filed and when any registration or qualification has become effective under a state securities or blue sky law or any exemption thereunder has been obtained, (B) promptly after receipt thereof, of any request by the Commission for the amendment or supplementing of such registration statement or prospectus or for additional information, and (C) at any time when a prospectus relating

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thereto is required to be delivered under the Securities Act, of the happening of any event as a result of which the prospectus included in such registration statement contains an untrue statement of a material fact or omits any fact necessary to make the statements therein not misleading, and, subject to Section 1(f), at the request of any such seller, the Issuer shall use its commercially reasonable efforts to prepare a supplement or amendment to such prospectus so that, as thereafter delivered to the purchasers of such Registrable Securities, such prospectus shall not contain an untrue statement of a material fact or omit to state any fact necessary to make the statements therein not misleading;

(vii)    use commercially reasonable efforts to cause all such Registrable Securities to be listed on the NYSE as set forth in Section 5.06 of the Agreement;

(viii)    use commercially reasonable efforts to provide a transfer agent and registrar for all such Registrable Securities not later than the Closing Date and use commercially reasonable efforts to procure the cooperation of such transfer agent and registrar in settling any offering or sale of Registrable Securities, including with respect to the transfer of physical stock certificates into book-entry form in accordance with any procedures reasonably requested by the majority of the holders of the Registrable Securities or the managing underwriter(s); in connection therewith, if reasonably required by the Issuer’s transfer agent and registrar, the Issuer shall, promptly after the effectiveness of the applicable registration statement, cause a customary opinion of counsel (which may be internal counsel) as to the removal of any restrictive legend to be delivered to its transfer agent and registrar, together with any other authorizations, certificates and directions required by the transfer agent which authorize and direct the transfer agent to issue such Registrable Securities without legend upon sale by the holder of such shares of Registrable Securities under the registration statement;

(ix)    enter into and perform such customary agreements (including underwriting agreements and “lock-up” agreements in customary form) and take all such other actions as the holders of a majority of the Registrable Securities being sold or the underwriters, if any, reasonably request in order to expedite or facilitate the disposition of such Registrable Securities (including, without limitation, causing the Issuer and any directors or officers of the Issuer to agree to be bound by customary “lock-up” agreements restricting the ability to dispose of Issuer securities and file or cause the filing of any registration statement under the Securities Act);

(x)    make available for inspection by any seller of Registrable Securities, any underwriter participating in any disposition pursuant to such registration statement and any attorney, accountant or other agent retained by any such seller or underwriter, all financial and other records, pertinent corporate and business documents and properties of the Issuer as shall be necessary to enable them to exercise their due diligence responsibility, and supply, and cause the Issuer’s officers, directors, employees, agents, representatives and independent accountants to supply, all information (including, without limitation, financial statements and financial data of the Issuer and its Subsidiaries) reasonably requested by any such seller, underwriter, attorney, accountant or agent in connection with such registration, disposition or marketing efforts;

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(xi)    take all reasonable actions to ensure that any Free Writing Prospectus utilized in connection with any Piggyback Registration hereunder complies in all material respects with the Securities Act, is filed in accordance with the Securities Act to the extent required thereby, is retained in accordance with the Securities Act to the extent required thereby and, when taken together with the related prospectus, shall not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements therein, in light of the circumstances under which they were made, not misleading;

(xii)    otherwise use its reasonable best efforts to comply with all applicable rules and regulations of the Commission, and make available to its security holders, as soon as reasonably practicable, an earnings statement covering the period of at least twelve months beginning with the first day of the Issuer’s first full calendar quarter after the effective date of the registration statement, which earnings statement shall satisfy the provisions of Section 11(a) of the Securities Act and Rule 158;

(xiii)    permit any holder of Registrable Securities which holder, in its sole and exclusive judgment, might be deemed to be an underwriter or a controlling person of the Issuer, to participate in the preparation of such registration or comparable statement and to allow such holder to provide language for insertion therein, in form and substance satisfactory to the Issuer, which in the reasonable judgment of such holder and its counsel should be included;

(xiv)    in the event any registration statement required to be filed under Section 1 ceases to be effective for any reason at any time during the period during which such registration statement is required to be kept effective (including as a result of the issuance of any stop order suspending the effectiveness of a registration statement, or the issuance of any order suspending or preventing the use of any related prospectus or suspending the qualification of any SiriusPoint Preference Shares included in such registration statement for sale in any jurisdiction), use reasonable best efforts promptly to cause such registration statement to again become effective or be declared effective under the Securities Act (including obtaining the prompt withdrawal of any such order or amending such registration statement or filing an additional registration statement);

(xv)    use its reasonable best efforts to cause such Registrable Securities covered by such registration statement to be registered with or approved by such other governmental agencies or authorities as may be necessary to enable the sellers thereof to consummate the disposition of such Registrable Securities;

(xvi)    cooperate with the holders of Registrable Securities covered by the registration statement and the managing underwriter or agent, if any, to facilitate the timely preparation and delivery of certificates (not bearing any restrictive legends) representing securities to be sold under the registration statement and enable such securities to be in such denominations and registered in such names as the managing underwriter, or agent, if any, or such holders may request at least 2 Business Days prior to any sale of Registrable Securities in a firm commitment public offering, but in any other such sale, within 10 Business Days prior to having to issue the Securities;

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(xvii)    cooperate with each holder of Registrable Securities covered by the registration statement and each underwriter or agent participating in the disposition of such Registrable Securities and their respective counsel in connection with any filings required to be made with FINRA;

(xviii)    use its commercially reasonable efforts to make available the executive officers of the Issuer to participate with the holders of Registrable Securities and any underwriters in any meetings, “road shows,” drafting sessions, rating agency presentations, due diligence sessions or other selling efforts that may be reasonably requested by the holders in connection with the marketing, resale, distribution or disposition of the Registrable Securities and to assist in preparation of presentations, teasers, offering memoranda and other customary marketing materials taking into account the Issuer’s reasonable business needs;

(xix)    use its commercially reasonable efforts to obtain one or more cold comfort letters from the Issuer’s independent public accountants in customary form and covering such matters of the type customarily covered by cold comfort letters;

(xx)    use its commercially reasonable efforts to provide a legal opinion and negative assurances letter of the Issuer’s outside counsel, dated the effective date of such registration statement (and, if such registration includes an underwritten Public Offering, dated the date of the closing under the applicable underwriting agreement), each amendment and supplement thereto, the prospectus included therein (including the preliminary prospectus) and such other documents relating thereto in customary form and covering such matters of the type customarily covered by legal opinions and negative assurances letters of such nature, which legal opinion and negative assurances letter shall be addressed to the underwriters;

(xxi)    if the Issuer files an Automatic Shelf Registration Statement covering any Registrable Securities, use its reasonable best efforts to remain a WKSI (and not become an ineligible issuer (as defined in Rule 405 under the Securities Act)) during the period during which such Automatic Shelf Registration Statement is required to remain effective;

(xxii)    if the Issuer does not pay the filing fee covering the Registrable Securities at the time an Automatic Shelf Registration Statement is filed, pay such fee at such time or times as the Registrable Securities are to be sold;

(xxiii)    if the Automatic Shelf Registration Statement has been outstanding for at least three (3) years, at the end of the third year, refile a new Automatic Shelf Registration Statement covering the Registrable Securities, and, if at any time when the Issuer is required to re-evaluate its WKSI status the Issuer determines that it is not a WKSI, use its reasonable best efforts to refile the Shelf Registration Statement on Form S-3 and, if such form is not available, Form S-1 and keep such registration statement effective during the period during which such registration statement is required to be kept effective;

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(xxiv)    provide any information or cooperation as reasonably requested in connection with any required and advisable regulatory approvals, consents or filings, including under applicable antitrust, securities and insurance Laws; and

(xxv)    take all other corporate, limited liability company, partnership or other similar actions reasonably requested by a Preferred Shareholder or any transaction counterparty in connection with the marketing, resale, distribution or disposition of the Registrable Securities.

(b)    The Issuer shall use its reasonable best efforts to cause any officer of the Issuer, for so long as he or she is employed by the Issuer or any Subsidiary thereof, to participate fully in the sale process in a manner customary for persons in like positions and consistent with his or her other duties with the Issuer, including the preparation of the registration statement or other marketing materials and the preparation and presentation of any “road shows” or other presentations.

(c)    If the Issuer files any Automatic Shelf Registration Statement for the benefit of the holders of any of its securities other than the holders of Registrable Securities, and the holders of Registrable Securities do not request that their Registrable Securities be included in such Shelf Registration Statement, the Issuer agrees that, at the request of any holder of the Registrable Securities, it shall include in such Automatic Shelf Registration Statement such disclosures as may be required by Rule 430B in order to ensure that the holders of the Registrable Securities may be added to such Shelf Registration Statement at a later time through the filing of a prospectus supplement rather than a post-effective amendment.

(d)    The Issuer may require each seller of Registrable Securities as to which any registration is being effected to furnish the Issuer such information regarding such seller and the registration and distribution of such securities as the Issuer may from time to time reasonably request in writing.

(e)    If any Preferred Shareholder or any of its respective Affiliates seek to effectuate an in-kind distribution of all or part of their respective Registrable Securities to their respective direct or indirect equityholders, the Issuer shall, subject to any applicable lock-ups, cooperate with the foregoing persons to facilitate such in-kind distribution in the manner reasonably requested.

Section 5.    Registration Expenses.

(a)    The Issuer’s Obligation. All expenses incident to the Issuer’s performance of or compliance with the provisions of this Annex (including, without limitation, all registration, qualification and filing fees; fees and expenses in connection with the listing of securities on any securities exchange or automated interdealer quotation system; fees and expenses of compliance with securities or blue sky laws; fees and expenses in connection with any review by FINRA; printing expenses; messenger and delivery expenses; fees and disbursements of custodians; and fees and disbursements of counsel for the Issuer, all independent certified public accountants (including in connection with any regular or special reviews or audits incident to or required by any registration) and other Persons retained by the Issuer; expenses of the Issuer relating to any

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analyst or investor presentations or any “road shows” undertaken in connection with the registration, marketing or selling of the Registrable Securities; and fees and expenses of any transfer agent and registrar and the fees and expenses of any other agent or trustee appointed in connection with a registration) (all such expenses being herein called “Registration Expenses”), shall be borne by the Issuer except as provided for in this Annex. The Issuer shall, in any event, pay its internal expenses (including, without limitation, all salaries and expenses of its officers and employees performing legal or accounting duties), the expense of any annual audit or quarterly review and the expense of any liability insurance. Each Person that sells securities pursuant to a Shelf Offering or Piggyback Registration hereunder shall bear and pay all underwriting discounts, selling commissions or fees, or any discount commissions or fees of selling brokers, dealers or similar securities industry professionals and transfer taxes applicable to the securities sold for such Person’s account.

(b)    Counsel Fees and Disbursements. In connection with each Piggyback Registration and each Shelf Offering that is an underwritten offering, the Issuer shall reimburse the holders of Registrable Securities included in such registration for the reasonable fees and disbursements of one counsel chosen by the holders of a majority of the Registrable Securities included in such registration or participating in such Shelf Offering.

(c)    Security Holders. To the extent Registration Expenses are not required to be paid by the Issuer, each holder of securities included in any registration hereunder shall pay those Registration Expenses allocable to the registration of such holder’s securities so included, and any Registration Expenses not so allocable shall be borne by all sellers of securities included in such registration in proportion to the aggregate selling price of the securities to be so registered.

Section 6.    Indemnification and Contribution.

(a)    By the Issuer. The Issuer shall indemnify and hold harmless, to the extent permitted by law, each holder of Registrable Securities, such holder’s officers, directors employees, agents and representatives, and each Person who controls such holder (within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act) (the “Indemnified Parties”) against all losses, claims, actions, damages, liabilities and expenses (including with respect to actions or proceedings, whether commenced or threatened, and including reasonable attorney fees and expenses) caused by, resulting from, arising out of, or are based upon: (i) any untrue or alleged untrue statement of material fact contained in (A) any registration statement, prospectus, preliminary prospectus or Free Writing Prospectus, or any amendment thereof or supplement thereto, (ii) any omission or alleged omission of a material fact required to be stated therein or necessary to make the statements therein not misleading or (iii) any violation or alleged violation by the Issuer of the Securities Act or state securities laws or any rule or regulation promulgated thereunder applicable to the Issuer and relating to action or inaction required of the Issuer in connection with any such registration. In addition, the Issuer will reimburse such Indemnified Party for any legal or any other expenses reasonably incurred by them in connection with investigating or defending any such losses. Notwithstanding the foregoing, the Issuer shall not be liable in any such case to the extent that any such losses result from, arise out of, are based upon, or relate to an untrue statement or alleged untrue statement, or omission or alleged omission, made in such registration statement, any such prospectus, preliminary prospectus or Free Writing Prospectus or any amendment or supplement thereto, in reliance upon, and in conformity with,

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written information prepared and furnished in writing to the Issuer by such Indemnified Party expressly for use therein or by such Indemnified Party’s failure to deliver a copy of the registration statement or prospectus or any amendments or supplements thereto after the Issuer has furnished such Indemnified Party with a sufficient number of copies of the same. In connection with an underwritten offering, the Issuer shall indemnify such underwriters, their officers and directors, and each Person who controls such underwriters (within the meaning of the Securities Act) to the same extent as provided above with respect to the indemnification of the Indemnified Parties.

(b)    By Each Security Holder. In connection with any registration statement in which a holder of Registrable Securities is participating, each such holder shall furnish to the Issuer in writing such information and affidavits as the Issuer reasonably requests for use in connection with any such registration statement or prospectus and, to the extent permitted by law, shall indemnify the Issuer, its officers, directors, employees, agents and representatives, and each Person who controls the Issuer (within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act) against any losses, claims, damages, liabilities, severally and not jointly, to which such holder or any such director or officer, any such underwriter or controlling person may become subject under the Securities Act or otherwise, insofar as such losses, claims, damages or liabilities (or actions or proceedings, whether commenced or threatened, in respect thereof) arise out of or are based upon (i) any untrue or alleged untrue statement of material fact contained in any registration statement or prospectus or Free Writing Prospectus or any amendment thereof or supplement thereto, (ii) any omission or alleged omission of a material fact required to be stated therein or necessary to make the statements therein not misleading, but only to the extent that such untrue statement or omission is made in such registration statement, any such prospectus or Free Writing Prospectus or any amendment or supplement thereto, in reliance upon and in conformity with written information prepared and furnished to the Issuer by such holder pertaining exclusively to such holder expressly for use therein or (iii) any violation by the holder of any rule or regulation promulgated under the Securities Act or any state securities laws applicable to the holder and relating to action or inaction required of the holder in connection with any such registration, and such holder shall reimburse the Issuer and each such director, officer, underwriter and controlling Person for any legal or any other expenses actually and reasonably incurred by them in connection with investigating, defending or settling any such loss, claim, liability, action or proceeding, provided that the obligation to indemnify and hold harmless shall be individual, not joint and several, for each holder and shall be limited to the net amount of proceeds received by such holder from the sale of Registrable Securities pursuant to such registration statement.

(c)    Claim Procedure. Any Person entitled to indemnification hereunder shall (i) give prompt written notice to the indemnifying party of any claim with respect to which it seeks indemnification (provided that the failure to give prompt notice shall impair any Person’s right to indemnification hereunder only to the extent such failure has prejudiced the indemnifying party) and (ii) unless in such indemnified party’s reasonable judgment a conflict of interest between such indemnified and indemnifying parties may exist with respect to such claim, permit such indemnifying party to assume the defense of such claim with counsel reasonably satisfactory to the indemnified party. If such defense is assumed, the indemnifying party shall not be subject to any liability for any settlement made by the indemnified party without its consent (but such consent shall not be unreasonably withheld, conditioned or delayed). An indemnifying party who is not entitled to, or elects not to, assume the defense of a claim shall not be obligated to pay the fees and

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expenses of more than one counsel for all parties indemnified by such indemnifying party with respect to such claim, unless in the reasonable judgment of any indemnified party a conflict of interest may exist between such indemnified party and any other of such indemnified parties with respect to such claim. In such instance, the conflicted indemnified parties shall have a right to retain one separate counsel, chosen by the holders of a majority of the Registrable Securities included in the registration if such holders are indemnified parties, at the expense of the indemnifying party.

(d)    Contribution. If the indemnification provided for in this Section 6 is held by a court of competent jurisdiction to be unavailable to, or is insufficient to hold harmless, an indemnified party or is otherwise unenforceable with respect to any loss, claim, damage, liability or action referred to herein, then the indemnifying party shall contribute to the amounts paid or payable by such indemnified party as a result of such loss, claim, damage, liability or action in such proportion as is appropriate to reflect the relative fault of the indemnifying party on the one hand and of the indemnified party on the other hand in connection with the statements or omissions which resulted in such loss, claim, damage, liability or action as well as any other relevant equitable considerations; provided that the maximum amount of liability in respect of such contribution shall be limited, in the case of each seller of Registrable Securities, to an amount equal to the net proceeds actually received by such seller from the sale of Registrable Securities effected pursuant to such registration. The relative fault of the indemnifying party and of the indemnified party shall be determined by reference to, among other things, whether the untrue or alleged untrue statement of a material fact or the omission to state a material fact relates to information supplied by the indemnifying party or by the indemnified party and the parties’ relative intent, knowledge, access to information and opportunity to correct or prevent such statement or omission. The parties hereto agree that it would not be just or equitable if the contribution pursuant to this Section 6(d) were to be determined by pro rata allocation or by any other method of allocation that does not take into account such equitable considerations. The amount paid or payable by an indemnified party as a result of the losses, claims, damages, liabilities or expenses referred to herein shall be deemed to include any legal or other expenses reasonably incurred by such indemnified party in connection with investigating or defending against any action or claim which is the subject hereof. No person guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of the Securities Act) shall be entitled to contribution from any Person who is not guilty of such fraudulent misrepresentation.

(e)    Release. No indemnifying party shall, except with the consent of the indemnified party, consent to the entry of any judgment or enter into any settlement that does not include as an unconditional term thereof a release from all liability in respect to such claim or litigation.

(f)    Non-exclusive Remedy; Survival. The indemnification and contribution provided for under this Annex shall be in addition to any other rights to indemnification or contribution that any indemnified party may have pursuant to law or contract and shall remain in full force and effect regardless of any investigation made by or on behalf of the indemnified party or any officer, director or controlling Person of such indemnified party and shall survive the transfer of Registrable Securities and the termination or expiration of the Agreement.

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Section 7.    Underwritten Offerings. No Person may participate in any registration hereunder which is underwritten unless such Person (i) agrees to sell such Person’s securities on the basis provided in any underwriting arrangements approved by the Person or Persons entitled hereunder to approve such arrangements and (ii) completes and executes all questionnaires, powers of attorney, custody agreements, indemnities, underwriting agreements and other documents required under the terms of such underwriting arrangements; provided that no holder of Registrable Securities included in any underwritten registration shall be required to make any representations or warranties to the Issuer or the underwriters (other than representations and warranties regarding such holder and such holder’s intended method of distribution) or to undertake any indemnification obligations to the Issuer or the underwriters with respect thereto that are materially more burdensome than those provided in Section 6. For the avoidance of doubt, each holder of Registrable Securities shall execute such powers of attorney or custody agreements as are requested by the managing underwriters, appointing as power of attorney or custodian such persons as reasonably requested by the Issuer. Each holder of Registrable Securities shall execute and deliver such other agreements as may be reasonably requested by the Issuer and the lead managing underwriter(s) that are consistent with such holder’s obligations under Section 3, Section 4 and this Section 7 or that are necessary to give further effect thereto. To the extent that any such agreement is entered into pursuant to, and consistent with, Section 3 and this Section 7, the respective rights and obligations created under such agreement shall supersede the respective rights and obligations of the holders, the Issuer and the underwriters created pursuant to this Section 7.

Section 8.    Current Public Information. At all times after the Issuer has filed a registration statement with the Commission pursuant to the requirements of either the Securities Act or the Exchange Act, the Issuer shall file all reports required to be filed by it under the Securities Act and the Exchange Act and shall take such further action as any holder or holders of Registrable Securities may reasonably request, all to the extent required to enable such holders to sell Registrable Securities pursuant to Rule 144. Upon request, the Issuer shall deliver to any holder of Registrable Securities a written statement as to whether it has complied with such requirements.

Section 9.    General Provisions.

(a)    No Inconsistent Agreements. The Issuer shall not hereafter enter into any agreement with respect to its Sirius Point Preference Shares which is inconsistent with or violates the rights granted to the holders of Registrable Securities in this Annex.

(b)    Transfer. For the avoidance of doubt, any transferee of all or any portion of (i) a Preferred Shareholder’s Series B Preference Shares or SiriusPoint Preference Shares pursuant to Section 9.07 of the Agreement or (ii) other Registrable Securities of any holder of Registrable Securities, in each case, shall be deemed to be a holder of Registrable Securities hereunder in the same manner as if such transferee were an original signatory to the Agreement, and the applicable SiriusPoint Preference Shares and Registrable Securities being transferred (or, in the case of a transfer of Series B Preference Shares, the SiriusPoint Preference Shares to be issued to such transferee in exchange for such Series B Preference Shares in the Exchange) shall be included as “Registrable Securities” hereunder.

Section 10.    Definitions. Unless otherwise set forth below or elsewhere in this Annex, other capitalized terms contained herein have the meanings set forth in the Agreement.

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“Automatic Shelf Registration Statement” has the meaning set forth in Section 1(a).

“Capital Stock” means (i) with respect to any Person that is a corporation, any and all shares, interests or equivalents in capital stock of such corporation (whether voting or nonvoting and whether common or preferred) and (ii) with respect to any Person that is not a corporation, individual or governmental entity, any and all partnership, membership, limited liability company or other equity interests of such Person that confer on the holder thereof the right to receive a share of the profits and losses of, or the distribution of assets of, the issuing Person, including in each case any and all warrants, rights (including conversion and exchange rights) and options to purchase any of the foregoing.

“Commission” means the Securities and Exchange Commission.

“Effectiveness Deadline” means, with respect to any registration statement required to be filed pursuant to Section 1, (a) the date such registration statement is filed, if the Issuer is a WKSI as of such date and such registration statement is an Automatic Shelf Registration Statement eligible to become immediately effective upon filing pursuant to Rule 462 under the 1933 Act; or (b) if the Issuer is not a WKSI as of the date such registration statement is filed, as soon as reasonably practicable, and no later than the 5th Business Day following the date on which the Issuer is notified by the Commission that such registration statement will not be reviewed or is not subject to further review and comments and will be declared effective upon request by the Issuer.

“End of Suspension Notice” has the meaning set forth in Section 1(f)(ii).

“Exchange Act” means the Securities Exchange Act of 1934, as amended from time to time, or any successor federal law then in force, together with all rules and regulations promulgated thereunder.

“FINRA” means the Financial Industry Regulatory Authority.

“Free Writing Prospectus” means a free writing prospectus, as defined in Rule 405.

“Holdback Period” has the meaning set forth in Section 3(a).

“Holder” means a holder of Registrable Securities.

“Indemnified Parties” has the meaning set forth in Section 6(a).

“Issuer” means, prior to the closing of the Merger, TPRe, and from and after the closing of the Merger, SiriusPoint.

“Piggyback Registrations” has the meaning set forth in Section 2(a).

“Public Offering” means any sale or distribution by the Issuer and/or holders of Registrable Securities to the public of any Capital Stock of the Issuer pursuant to an offering registered under the Securities Act.

“Registrable Securities” means (i) any SiriusPoint Preference Shares issued pursuant to the Agreement or distributed (directly or indirectly) to the Preferred Shareholders or any of their

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respective Affiliates and (ii) any Capital Stock of the Issuer or any Subsidiary of the Issuer issued or issuable with respect to the securities referred to in clause (i) above by way of dividend, distribution, split, exchange, redemption right, reclassification or combination of securities, or any recapitalization, merger, consolidation or other reorganization. As to any particular Registrable Securities, such securities shall cease to be Registrable Securities (a) when they cease to be outstanding, (b) when they have been sold or distributed pursuant to a Public Offering, (c) when they have been sold in compliance with Rule 144 or (d) repurchased by the Issuer or a Subsidiary of the Issuer. Notwithstanding the foregoing, any Registrable Securities held by any Person that may be sold under clause (b)(1)(i) of Rule 144 without limitation under any of the other requirements of Rule 144 shall not be deemed to be Registrable Securities. For purposes of this Annex, a Person shall be deemed to be a holder of Registrable Securities, and the Registrable Securities shall be deemed to be in existence, whenever such Person has the right to acquire, directly or indirectly, such Registrable Securities (upon conversion or exercise in connection with a transfer of securities or otherwise, but disregarding any restrictions or limitations upon the exercise of such right), whether or not such acquisition has actually been effected, and such Person shall be entitled to exercise the rights of a holder of Registrable Securities hereunder.

“Registration Expenses” has the meaning set forth in Section 5(a).

“Rule 144”, “Rule 158”, “Rule 405”, “Rule 415” and “Rule 462” mean, in each case, such rule promulgated under the Securities Act (or any successor provision) by the Commission, as the same shall be amended from time to time, or any successor rule then in force.

“Sale Transaction” has the meaning set forth in Section 3(a).

“Securities” has the meaning set forth in Section 3(a).

“Shelf Offering” has the meaning set forth in Section 1(b).

“Shelf Offering Notice” has the meaning set forth in Section 1(b).

“Shelf Registrable Securities” has the meaning set forth in Section 1(b).

“Shelf Registration” has the meaning set forth in Section 1(a).

“Shelf Registration Statement” has the meaning set forth in Section 1(a).

“Suspension Event” has the meaning set forth in Section 1(f)(ii).

“Suspension Notice” has the meaning set forth in Section 1(f)(ii).

“Suspension Period” has the meaning set forth in Section 1(f)(i).

“WKSI” means a “well-known seasoned issuer” as defined under Rule 405.

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EXHIBIT A

CERTIFICATE OF DESIGNATION

OF

8.00% RESETTABLE FIXED RATE PREFERENCE SHARES, SERIES B

OF

SIRIUSPOINT LTD.

SiriusPoint Ltd. (formerly known as Third Point Reinsurance Ltd.), a Bermuda exempted company limited by shares (the “Company”), HEREBY CERTIFIES that, pursuant to the authority contained in its Amended and Restated Bye-Laws (as amended and restated from time to time, the “Bye-Laws”) and to resolutions of the board of directors of the Company (the “Board of Directors”) adopted on [●], 202[●], the creation of the series of 8.00% Resettable Fixed Rate Preference Shares, Series B, US$0.10 par value per share, US$25.00 liquidation preference per share (the “Series B Preference Shares”), was authorized and the designation, preferences and privileges, voting rights, relative, participating, optional and other special rights, and qualifications, limitations and restrictions of the Series B Preference Shares, in addition to those set forth in the Memorandum of Association and the Bye-Laws of the Company, were fixed as follows:

SECTION 1.    DESIGNATION. The distinctive serial designation of the Series B Preference Shares is “8.00% Resettable Fixed Rate Preference Shares, Series B.” Each Series B Preference Share shall be identical in all respects to every other Series B Preference Share, except as to issue price, the date of issuance and the respective dates from which dividends thereon shall accrue, to the extent such dates may differ as permitted pursuant to Section 4(a) herein.

SECTION 2.    NUMBER OF SHARES. The authorized number of Series B Preference Shares shall initially be [●]. The Company may from time to time elect to issue additional Series B Preference Shares, and all the additional shares so issued shall be a part of, and form a single series with, the Series B Preference Shares initially authorized hereby. Series B Preference Shares that are redeemed, purchased or otherwise acquired by the Company shall have the status of authorized but unissued shares of the Company, without designation as to class or series.

SECTION 3.    DEFINITIONS. As used herein with respect to Series B Preference Shares:

(a)    “additional amounts” has the meaning specified in Section 5(a).

(b)    “Applicable Supervisor” means the BMA, or, should the BMA no longer have jurisdiction or responsibility to regulate the Company or the Insurance Group, as the context requires, a regulator which is otherwise subject to Applicable Supervisory Regulations.

(c)    “Applicable Supervisory Regulations” means such insurance supervisory laws, rules and regulations relating to group supervision or the supervision of single insurance entities, as applicable, which are applicable to the Company or the Insurance Group, and which

1

shall initially mean the Group Rules until such time when the BMA no longer has jurisdiction or responsibility to regulate the Company or the Insurance Group.

(d)    “Bermuda Business Day” means any day other than a day on which commercial banks in Bermuda are authorized or obligated by law, executive order or regulation to close.

(e)    “BMA” means the Bermuda Monetary Authority.

(f)    “Business Day” means a day that is a Monday, Tuesday, Wednesday, Thursday or Friday and is not a day on which banking institutions in New York City generally are authorized or obligated by law or executive order to close.

(g)    “Calculation Agent” means the nationally recognized calculation agent appointed by the Company prior to the First Reset Date.

(h)    “Capital Adequacy Regulations” means the solvency margin, capital adequacy regulations or any other regulatory capital rules applicable to the Company from time to time on an individual or group basis pursuant to Bermuda law and/or the laws of any other relevant jurisdiction and which set out the requirements to be satisfied by financial instruments to qualify as solvency margin or additional solvency margin or regulatory capital (or any equivalent terminology employed by the then-applicable capital adequacy regulations).

(i)    “Capital Disqualification Event” means that the Series B Preference Shares do not qualify, in whole or in part (including as a result of any transitional or grandfathering provisions or otherwise), for purposes of determining the solvency margin, capital adequacy ratios or any other comparable ratios, regulatory capital resource or level, of the Company or any subsidiary thereof, where capital is subdivided into tiers, as at least Tier 2 capital securities, under then-applicable Capital Adequacy Regulations imposed upon the Company by the Applicable Supervisor, which would include, without limitation, the Company’s Enhanced Capital Requirement, except as a result of any applicable limitation on the amount of such capital.

(j)    “Certificate of Designation” means this Certificate of Designation relating to the Series B Preference Shares, as may be amended from time to time.

(k)    “Code” means the Internal Revenue Code of 1986, as amended.

(l)    “Common Shares” means the common shares, par value US$0.10 per share, of the Company.

(m)    “Companies Act” means the Companies Act 1981 of Bermuda, as amended.

(n)    “Dividend Payment Date” has the meaning specified in Section 4(a).

(o)    “Dividend Period” has the meaning specified in Section 4(a).

(p)    “Dividend Rate” means (i) from and including the Issue Date, to but excluding the First Reset Date, an amount equal to 8.00% of US$25.00 per annum and (ii) from and including the First Reset Date, during each Reset Period, an amount equal to (A) the greater of

2

(x) the Five-Year U.S. Treasury Rate as of the most recent Reset Dividend Determination Date and (y) zero, plus (B) [●]%1 of US$25.00 per annum; provided, that beginning on and after [●], 202[●]2, for so long as any Series B Preference Shares remain outstanding, if and to the extent that the Series B Preference Shares are not, or have ceased to be, listed on the New York Stock Exchange, the applicable Dividend Rate shall increase by 1.00% of US$25.00 per annum until such time as the Series B Preference Shares are so listed; provided further that no such increase in the Dividend Rate shall occur if the Company has complied with Section 17 hereof and the New York Stock Exchange does not permit the Series B Preference Shares to be so listed.

(q)    “Dividend Record Date” has the meaning specified in Section 4(a).

(r)    “DTC” means The Depository Trust Company, together with its successors and assigns.

(s)    “Enhanced Capital Requirement” means the enhanced capital and surplus requirement applicable to the Insurance Group and as defined in the Insurance Act or, should the Insurance Act or the Group Rules no longer apply to the Insurance Group, any and all other solvency capital requirements or any other requirement to maintain assets applicable to the Company or in respect of the Insurance Group, as applicable, pursuant to the Applicable Supervisory Regulations.

(t)    “Exchange Act” means the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder.

(u)    “First Reset Date” means [●], 202[●]3.

(v)    “Five-Year U.S. Treasury Rate” means, as of any Reset Dividend Determination Date, as applicable:

(i)    an interest rate (expressed as a decimal) determined to be the per annum rate equal to the average of the yields to maturity for the five Business Days immediately prior to such Reset Dividend Determination Date for U.S. Treasury securities with a maturity of five years from the next Reset Date appearing under the caption “Treasury Constant Maturities” in the most recently published statistical release designated H.15 Daily Update or any successor publication which is published by the Federal Reserve Board, as determined by the Calculation Agent; or

(ii)    if there is no such published U.S. Treasury security with a maturity of five years from the next Reset Date and trading in the public securities markets, then the rate will be determined by interpolation between the average of the yields to maturity for the five Business Days immediately prior to such Reset Dividend Determination Date for two series of U.S. Treasury securities trading in the public securities market, (A) one maturing as close as possible to, but earlier than, the Reset Date following the next

1NTD: Amount to equal the difference between the initial rate (8.00%) and the Five-Year U.S. Treasury Rate at the time of pricing.

2NTD: Insert date that is 120 days from the Issue Date

3NTD: Insert date that is five years from the date that the issuance of these SiriusPoint Preference Shares is settled.

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succeeding Reset Dividend Determination Date, and (B) the other maturity as close as possible to, but later than, the Reset Date following the next succeeding Reset Dividend Determination Date, in each case as published in the most recently published statistical release designated H.15 Daily Update under the caption “Treasury Constant Maturities” or any successor publication which is published by the Federal Reserve Bank. The Five-Year U.S. Treasury Rate will be determined by the Calculation Agent on the applicable Reset Dividend Determination Date. If the Five-Year U.S. Treasury Rate cannot be determined pursuant to the methods described in clauses (i) or (ii) above, then the Five-Year U.S. Treasury Rate will be the same interest rate determined for the prior Reset Dividend Determination Date.

(w)    “Group Rules” means the Group Solvency Standards, together with the Group Supervision Rules.

(x)    “Group Solvency Standards” means the Bermuda Insurance (Prudential Standards) (Insurance Group Solvency Requirement) Rules 2011, as those rules and regulations may be amended or replaced from time to time.

(y)    “Group Supervision Rules” means the Bermuda Insurance (Group Supervision) Rules 2011, as those rules and regulations may be amended or replaced from time to time.

(z)    “Insurance Act” means the Bermuda Insurance Act 1978, as amended from time to time.

(aa)    “Insurance Group” means all of the subsidiaries of the Company that are regulated insurance or reinsurance companies (or part of such regulatory group) pursuant to the Applicable Supervisory Regulations.

(bb)    “Issue Date” means [●], 202[●], the initial date of issuance of the Series B Preference Shares.

(cc)    “Junior Shares” means any class or series of shares of the Company that ranks junior to the Series B Preference Shares either as to the payment of dividends or as to the distribution of assets upon any liquidation, dissolution or winding-up of the Company. As of the Issue Date, the Company’s Junior Shares outstanding consist of its Common Shares and its Series A Preference Shares.

(dd)    “Liquidation Preference” has the meaning specified in Section 6(b).

(ee)    “Memorandum of Association” means the memorandum of association of the Company, as it may be amended from time to time.

(ff)    “Nonpayment Event” has the meaning specified in Section 9(b).

(gg)    “Parity Shares” means any class or series of shares of the Company that ranks equally with the Series B Preference Shares as to the payment of dividends and as to the

4

distribution of assets on any liquidation, dissolution or winding-up of the Company. As of the Issue Date, there are no Parity Shares of the Company outstanding.

(hh)    “Preference Shares” means any and all series of preference shares of the Company, including the Series B Preference Shares.

(ii)    “Preference Shares Directors” has the meaning specified in Section 9(b).

(jj)    “Rating Agency” means a nationally recognized statistical rating organization, as defined in Section 3(a)(62) of the Exchange Act that publishes a rating for the Company as of the Issue Date.

(kk)    “Rating Agency Event” has the meaning specified in Section 7(e).

(ll)    “Redemption Date” means any date fixed for redemption in accordance with Section 7.

(mm)    “Redemption Requirements” has the meaning specified in Section 7(b).

(nn)    “Redemption Shares” means the Common Shares then issuable upon redemption of the Series B Preference Shares in accordance with the terms of Section 7.

(oo)    “Relevant Date” has the meaning specified in Section 5(b)(i).

(pp)    “Relevant Taxing Jurisdiction” has the meaning specified in Section 7(d).

(qq)     “Reset Date” means the First Reset Date and each date falling on the fifth anniversary of the preceding Reset Date, which in each case, will not be adjusted for Business Days.

(rr)    “Reset Dividend Determination Date” means, in respect of any Reset Period, the day falling three Business Days prior to the beginning of such Reset Period.

(ss)    “Reset Period” means the period from, and including, the First Reset Date to, but excluding, the next following Reset Date and thereafter each period from, and including, each Reset Date to, but excluding, the next following Reset Date.

(tt)    “Senior Shares” means any class or series of shares of the Company that ranks senior to the Series B Preference Shares either as to the payment of dividends or as to the distribution of assets upon any liquidation, dissolution or winding-up of the Company. As of the Issue Date, there are no Senior Shares of the Company outstanding.

(uu)    “Series A Preference Shares” mean the Series A Preference Shares, with a par value of US $0.10 per share, issued on the Issue Date.

(vv)    “Series B Preference Shares” has the meaning specified in the preamble.

(ww)    “set aside” in the context of any payment, means, without any action other than the following, the recording by the Company in its accounting ledgers of any accounting or

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bookkeeping entry which indicates, pursuant to a declaration of a dividend or other distribution by the Board of Directors, the allocation of the funds to be so paid on any class or series of the Company’s shares; provided, that if any funds for any class or series of Junior Shares or any class or series of Parity Shares are placed in a separate account of the Company or delivered to a disbursing, paying or other similar agent, then “set aside” with respect to the Series B Preference Shares shall mean placing such funds in a separate account or delivering such funds to a disbursing, paying or other similar agent.

(xx)    “Successor Company” means an entity formed by a consolidation, merger, amalgamation or other similar transaction involving the Company or the entity to which the Company conveys, transfers or leases all or substantially all of its properties and assets.

(yy)    “Tax Event” has the meaning specified in Section 7(d).

(zz)     “Voting Preference Shares” means any other class or series of Preference Shares ranking equally with the Series B Preference Shares with respect to dividends and the distribution of assets upon liquidation, dissolution or winding up of the Company and upon which like voting rights have been conferred and are exercisable. As of the Issue Date, there are no other Voting Preference Shares of the Company outstanding.

SECTION 4.    DIVIDENDS.

(a)    RATE AND PAYMENT OF DIVIDENDS. The holders of Series B Preference Shares will be entitled to receive, when, as and if declared by the Board of Directors or a duly authorized committee of the Board of Directors, out of lawfully available funds for the payment of dividends, cumulative cash dividends from, and including, the Issue Date, quarterly in arrears, on the last day of February, May, August and November of each year (each, a “Dividend Payment Date”), from and including on [●], 202[●]4; provided that, if any Dividend Payment Date falls on a day that is not a Business Day that is also a Bermuda Business Day, such dividend shall instead be payable on (and no additional dividends shall accrue on the amount so payable from such date to) the first Business Day that is also a Bermuda Business Day following such Dividend Payment Date.

Subject to the first sentence of Section 4(a), dividends shall be payable, with respect to each Dividend Period, in an amount per Series B Preference Share equal to the Dividend Rate. Dividends payable on the Series B Preference Shares shall be computed on the basis of a 360-day year consisting of twelve 30-day months with respect to a full Dividend Period, and on the basis of the actual number of days elapsed during such Dividend Period with respect to a Dividend Period other than a full Dividend Period.

Dividends that are payable on Series B Preference Shares on any Dividend Payment Date shall be payable to holders of record of Series B Preference Shares as they appear on the books on the register of members of the Company at 5:00 p.m. (New York City time) on the applicable record date, which shall be the 15th calendar day before that Dividend Payment Date or such other record date fixed by the Board of Directors or a duly authorized committee of the Board of Directors that is not more than 30 nor less than 10 days prior to such Dividend Payment Date

4NTD: Insert first Dividend Payment Date after the Issue Date.

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(each, a “Dividend Record Date”). Any such day that is a Dividend Record Date shall be a Dividend Record Date whether or not such day is a Business Day that is also a Bermuda Business Day.

Each dividend period (a “Dividend Period”) shall commence on and include a Dividend Payment Date (other than the initial Dividend Period, which shall commence on and include the Issue Date, provided that, for any Series B Preference Shares issued after the Issue Date, the initial Dividend Period for such shares may commence on and include such other date as the Board of Directors or a duly authorized committee of the Board of Directors shall determine and publicly disclose at the time such additional shares are issued) and shall end on, but exclude, the next Dividend Payment Date. Dividends payable in respect of a Dividend Period shall be payable in arrears (i.e., on the first Dividend Payment Date after such Dividend Period).

Dividends on the Series B Preference Shares shall be cumulative. Dividends on each Series B Preference Share shall accrue from, and including, the Issue Date, whether or not declared, and whether or not there are earnings or profits, surplus or other funds or assets of the Company legally available for the payment of dividends.

Holders of Series B Preference Shares shall not be entitled to any dividends or other distributions, whether payable in cash, securities or other property, in excess of full cumulative dividends payable on the Series B Preference Shares as specified in this Section 4 (subject to the other provisions of this Certificate of Designations).

(b)    PRIORITY OF DIVIDENDS. So long as any Series B Preference Shares remain outstanding, unless full cumulative dividends for all past Dividend Periods on all outstanding Series B Preference Shares have been declared and paid (or declared and a sum sufficient for the payment thereof has been set aside), (i) no dividend shall be declared or paid on the Common Shares or any other Junior Shares, other than a dividend payable solely in Common Shares or other Junior Shares, as applicable, and (ii) no Common Shares or other Junior Shares shall be purchased, redeemed or otherwise acquired for consideration by the Company, directly or indirectly (other than (A) as a result of a reclassification of Junior Shares for or into other Junior Shares, or the exchange or conversion of one Junior Share for or into another Junior Share, (B) through the use of the proceeds of a substantially contemporaneous sale of Junior Shares or (C) as required by or necessary to fulfill the terms of any employment contract, benefit plan or similar arrangement with or for the benefit of one or more employees, directors or consultants). For the avoidance of doubt, the Series A Preference Shares may be forfeited, issued and converted into Common Shares in accordance with the terms of the Series A Preference Shares.

(c)    RESTRICTIONS ON PAYMENT OF DIVIDENDS. Pursuant to and subject to the Companies Act, the Company may not lawfully declare or pay a dividend if the Company has reasonable grounds for believing that the Company is, or would after payment of the dividend be, unable to pay its liabilities as they become due, or that the realizable value of the Company’s assets would, after payment of the dividend, be less than the aggregate value of the Company’s liabilities. Additionally, dividends on the Series B Preference Shares will not be declared, paid or set aside for payment if the Company is, or after giving effect to such act would be, in breach of the Insurance Act, the Companies Act, the Insurance (Eligible Capital) Rules 2012,

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the Group Solvency Standard, including the Enhanced Capital Requirement, or under such other Applicable Supervisory Regulations or other applicable laws, rules and regulations.

SECTION 5.    PAYMENT OF ADDITIONAL AMOUNTS.

(a)    The Company shall make all payments on the Series B Preference Shares free and clear of and without withholding or deduction at source for, or on account of, any present or future taxes, fees, duties, assessments or governmental charges of whatever nature imposed or levied by or on behalf of any Relevant Taxing Jurisdiction, unless such taxes, fees, duties, assessments or governmental charges are required to be withheld or deducted by (i) the laws (or any regulations or rulings promulgated thereunder) of any Relevant Taxing Jurisdiction or (ii) an official position regarding the application, administration, interpretation or enforcement of any such laws, regulations or rulings (including, without limitation, a holding by a court of competent jurisdiction or by a taxing authority in any Relevant Taxing Jurisdiction). If a withholding or deduction at source is required, the Company shall, subject to certain limitations and exceptions described below, pay to the holders of the Series B Preference Shares such additional amounts (the “additional amounts”) as dividends as may be necessary so that every net payment, after such withholding or deduction (including any such withholding or deduction from such additional amounts), shall be equal to the amounts the Company would otherwise have been required to pay had no such withholding or deduction been required.

(b)    The Company shall not be required to pay any additional amounts for or on account of:

(i)    any tax, fee, duty, assessment or governmental charge of whatever nature that would not have been imposed but for the fact that (x) such holder was a resident, domiciliary or national of, or engaged in business or maintained a permanent establishment or was physically present in, the Relevant Taxing Jurisdiction or any political subdivision thereof or otherwise had some connection with the Relevant Taxing Jurisdiction other than by reason of the mere ownership of, or receipt of payment under, such Series B Preference Shares, or (y) any Series B Preference Shares were presented for payment (where presentation is required for payment) more than 30 days after the Relevant Date (except to the extent that the holder would have been entitled to such amounts if it had presented such shares for payment on any day within such 30 day period). The “Relevant Date” means, in respect of any payment, the date on which such payment first becomes due and payable, but if the full amount of the moneys payable has not been received by the dividend disbursing agent on or prior to such due date, it means the first date on which the full amount of such moneys having been so received and being available for payment to holders and notice to that effect shall have been duly given to the holders of the Series B Preference Shares;

(ii)    any estate, inheritance, gift, sale, transfer, personal property or similar tax, assessment or other governmental charge or any tax, assessment or other governmental charge that is payable otherwise than by withholding or deduction from payment of the liquidation preference or of any dividends on the Series B Preference Shares;

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(iii)    any tax, fee, duty, assessment or other governmental charge that is imposed or withheld by reason of the failure by the holder of such Series B Preference Shares to comply with any reasonable request by the Company addressed to the holder within 90 days of such request (a) to provide information concerning the nationality, residence or identity of the holder or (b) to make any declaration or other similar claim or satisfy any information or reporting requirement that is required or imposed by statute, treaty, regulation or administrative practice of the Relevant Taxing Jurisdiction as a precondition to exemption from all or part of such tax, fee, duty, assessment or other governmental charge;

(iv)    any tax, fee, duty, assessment or governmental charge required to be withheld or deducted under Sections 1471 through 1474 of the Code (or any Treasury regulations or other administrative guidance thereunder), any agreements entered into under section 1471(b)(1) of the Code, intergovernmental agreements relating to the foregoing or any fiscal or regulatory legislation, rules or practices adopted pursuant to any such intergovernmental agreement; or

(v)    any combination of items (i), (ii), (iii) and (iv).

In addition, the Company shall not pay additional amounts with respect to any payment on any such Series B Preference Shares to any holder that is a fiduciary, partnership, limited liability company or other pass-through entity other than the sole beneficial owner of such Series B Preference Shares if such payment would be required by the laws of the Relevant Taxing Jurisdiction to be included in the income for tax purposes of a beneficiary or partner or settlor with respect to such fiduciary or a member of such partnership, limited liability company or other pass-through entity or a beneficial owner to the extent such beneficiary, partner or settlor would not have been entitled to such additional amounts had it been the holder of the Series B Preference Shares.

SECTION 6.    LIQUIDATION RIGHTS.

(a)    VOLUNTARY OR INVOLUNTARY LIQUIDATION. In the event of any liquidation, dissolution or winding-up of the Company, whether voluntary or involuntary, holders of the Series B Preference Shares shall be entitled to receive, out of the assets of the Company available for distribution to shareholders of the Company, after satisfaction of all liabilities and obligations to creditors and Senior Shares of the Company (including provision (reserves) for policyholder obligations of the Company’s subsidiaries), if any, but before any distribution of such assets is made to the holders of Common Shares and any other Junior Shares, a liquidating distribution in the amount equal to US$25.00 per Series B Preference Share, plus any unpaid, accrued cumulative dividends, whether or not declared, on such Series B Preference Share, without interest on such unpaid dividends, to the date fixed for distribution.

(b)    PARTIAL PAYMENT. After payment of the full amount of any distribution described in 6(a) above to which holders are entitled, holders of the Series B Preference Shares will have no right or claim to any of the Company’s remaining assets. If in any distribution described in Section 6(a) above, the assets of the Company are not sufficient to pay the Liquidation Preferences (as defined below) in full to all holders of Series B Preference Shares and

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all holders of any Parity Shares, the amounts payable to the holders of Series B Preference Shares and to the holders of all such other Parity Shares shall be paid pro rata in accordance with the respective aggregate Liquidation Preferences of the holders of Series B Preference Shares and the holders of all such other Parity Shares, but only to the extent the Company has assets available after satisfaction of all liabilities to creditors and holders of Senior Shares. In any such distribution, the “Liquidation Preference” of any holder of Series B Preference Shares or Parity Shares of the Company shall mean the amount otherwise payable to such holder in such distribution (assuming no limitation on the assets of the Company available for such distribution), including any unpaid, accrued cumulative dividends, whether or not declared, in the case of any holder of Series B Preference Shares or any holder of Parity Shares on which dividends accrue on a cumulative basis (but excluding any dividends that had not previously been declared with respect to any non-cumulative Parity Shares).

(c)    RESIDUAL DISTRIBUTIONS. If the Liquidation Preference has been paid in full to all holders of Series B Preference Shares and any holders of Parity Shares, the holders of Junior Shares of the Company shall be entitled to receive all remaining assets of the Company according to their respective rights and preferences.

(d)    CONTRACTUAL SUBORDINATION. The Series B Preference Shares shall be subordinated in right of payment to all obligations of the Company’s subsidiaries, including all existing and future policyholders’ obligations of such subsidiaries.

(e)    MERGER, CONSOLIDATION AND SALE OF ASSETS NOT LIQUIDATION. For purposes of this Section 6, the consolidation, amalgamation, merger, arrangement, reincorporation, de-registration, reconstruction, reorganization or other similar transaction involving the Company or the sale or transfer of all or substantially all of the shares or the property or business of the Company shall not be deemed to constitute a liquidation, dissolution or winding-up.

SECTION 7.    OPTIONAL REDEMPTION.

(a)    The Series B Preference Shares are perpetual and have no fixed maturity date. The Series B Preference Shares may not be redeemed by the Company except as set forth in Sections 7(b), (c), (d) and (e) herein.

(b)    REDEMPTION AFTER FIRST RESET DATE. The Company may redeem the Series B Preference Shares, in whole or in part, upon notice given as provided in Section 7(h) herein, on the First Reset Date and on any subsequent Reset Date, at a redemption price equal to US$25.00 per Series B Preference Share, plus any unpaid, accrued cumulative dividends, whether or not declared, on such Series B Preference Share, to, but excluding, the Redemption Date, without interest on such unpaid dividends; provided that no such redemption may occur unless either (1) the Company has sufficient funds in order to meet the Enhanced Capital Requirement and the Applicable Supervisor approves of the redemption or (2) the Company replaces the capital represented by Series B Preference Shares to be redeemed with capital having equal or better capital treatment as the Series B Preference Shares under the Enhanced Capital Requirement (the conditions described in clauses (1) and (2), the “Redemption Requirements”). In the event the

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applicable Redemption Date is not a Business Day, the redemption price will be paid on the next Business Day without any adjustment to the amount of the redemption price paid.

(c)    CAPITAL DISQUALIFICATION EVENT. The Company may redeem, in whole, but not in part, all of the Series B Preference Shares, upon notice given as provided in Section 7(h) herein, at a redemption price equal to US$25.00 per Series B Preference Share, plus any unpaid, accrued cumulative dividends, whether or not declared, on such Series B Preference Share, to, but excluding, the Redemption Date, without interest on such unpaid dividends, at any time within 90 days following the occurrence of the date on which the Company has reasonably determined, based on the advice of external legal, financial and tax advisers with knowledge of such matters, as applicable, that, as a result of (i) any amendment to, or change in, those laws or regulations of the jurisdiction of the Applicable Supervisor that is enacted or becomes effective after the Issue Date or (ii) any official administrative decision or judicial decision or administrative action or other official pronouncement interpreting or applying those laws or regulations that are announced after the Issue Date, a Capital Disqualification Event has occurred; provided that no such redemption may occur unless one of the Redemption Requirements is satisfied.

(d)    ADDITIONAL AMOUNTS. The Company may redeem, in whole, but not in part, all of the Series B Preference Shares, upon notice given as provided in Section 7(h) herein, at a redemption price equal to US$25.00 per Series B Preference Share, plus any unpaid, accrued cumulative dividends, whether or not declared, on such Series B Preference Share, to, but excluding, the Redemption Date, without interest on such unpaid dividends, if there is, in the Company’s reasonable determination, based on the advice of external legal, financial and tax advisers with knowledge of such matters, as applicable, a substantial probability that the Company or any Successor Company would become obligated to pay additional amounts on the next succeeding Dividend Payment Date with respect to the Series B Preference Shares and the payment of those additional amounts could not be avoided by the use of any reasonable measures available to the Company or any Successor Company (a “Tax Event”); provided that no such redemption may occur unless one of the Redemption Requirements is satisfied. As used herein, “Relevant Taxing Jurisdiction” means (A) Bermuda or any political subdivision or governmental authority of or in Bermuda with the power to tax, (B) any jurisdiction from or through which the Company or its dividend disbursing agent is making payments on the Series B Preference Shares or any political subdivision or governmental authority of or in that jurisdiction with the power to tax or (C) any other jurisdiction in which the Company or any Successor Company is organized or generally subject to taxation or any political subdivision or governmental authority of or in that jurisdiction with the power to tax. Prior to any redemption upon a Tax Event, the Company shall file with its corporate records and deliver to the transfer agent for the Series B Preference Shares a certificate signed by one of the Company’s officers confirming that a Tax Event has occurred and is continuing (as reasonably determined by the Company based on the advice of external tax and legal advisers). The Company shall include a copy of this certificate with any notice of such redemption.

(e)    RATING AGENCY EVENT. The Company may redeem, in whole, but not in part, all of the Series B Preference Shares, upon notice given as provided in Section 7(h) herein, at a redemption price equal to US$25.50 per Series B Preference Share, plus any unpaid, accrued cumulative dividends, whether or not declared, on such Series B Preference Share, to, but

11

excluding, the Redemption Date, without interest on such unpaid dividends, within 90 days after a Rating Agency amends, clarifies or changes the criteria it uses to assign equity credit to securities such as the Series B Preference Shares, which amendment, clarification or change results in a Rating Agency Event; provided that no such redemption may occur unless one of the Redemption Requirements is satisfied. As used herein, a “Rating Agency Event” occurs if any Rating Agency that then publishes a rating for the Company amends, clarifies or changes the criteria it uses to assign equity credit to securities such as the Series B Preference Shares, which amendment, clarification, or change results in:

(i)    the shortening of the length of time the Series B Preference Shares are assigned a particular level of equity credit by that Rating Agency as compared to the length of time they would have been assigned that level of equity credit by that Rating Agency or its predecessor on the initial issuance of the Series B Preference Shares; or

(ii)    the lowering of the equity credit (including up to a lesser amount) assigned to the Series B Preference Shares by that Rating Agency as compared to the equity credit assigned by that Rating Agency or its predecessor on the initial issuance of the Series B Preference Shares.

(f)    NO SINKING FUND. The Series B Preference Shares shall not be subject to any mandatory redemption, sinking fund, retirement fund or purchase fund or other similar provisions. Holders of Series B Preference Shares shall have no right to require redemption, repurchase or retirement of any Series B Preference Shares.

(g)    PROCEDURES FOR REDEMPTION. The redemption price for any Series B Preference Shares shall be payable on the Redemption Date to the holders of such shares against book-entry transfer or surrender of the certificate(s) evidencing such shares to the Company or its agent. Prior to delivering any notice of redemption as provided below, the Company shall file with its corporate records a certificate signed by one of the Company’s officers affirming the Company’s compliance with the redemption provisions under the Companies Act relating to the Series B Preference Shares, and stating that there are reasonable grounds for believing that the Company is, and after the redemption will be, able to pay its liabilities as they become due and that the redemption will not cause the Company to breach any provision of applicable Bermuda law or regulation. The Company shall mail a copy of this certificate with the notice of any redemption.

(h)    NOTICE OF REDEMPTION. Notice of every redemption of Series B Preference Shares shall be given by first class mail, postage prepaid, addressed to the holders of record of the Series B Preference Shares to be redeemed at their respective last addresses appearing on the share register of the Company. Such mailing shall be at least 15 days and not more than 60 days before the date fixed for redemption. Any notice mailed as provided in this subsection shall be conclusively presumed to have been duly given, whether or not the holder receives such notice, but failure duly to give such notice by mail, or any defect in such notice or in the mailing thereof, to any holder of Series B Preference Shares designated for redemption shall not affect the validity of the proceedings for the redemption of any other Series B Preference Shares. Notwithstanding the foregoing, if the Series B Preference Shares or any depositary shares representing interests in the Series B Preference Shares are issued in book-entry form through DTC or any other similar facility, notice of redemption and a copy of this certificate may be given to the holders of Series B

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Preference Shares at such time and in any manner permitted by such facility. Each such notice given to a holder shall state: (i) the Redemption Date; (ii) the number of Series B Preference Shares to be redeemed and, if less than all the Series B Preference Shares held by such holder are to be redeemed, the number of such Series B Preference Shares to be redeemed from such holder; (iii) the redemption price; and (iv) that the Series B Preference Shares should be delivered via book-entry transfer or the place or places where certificates, if any, for such Series B Preference Shares are to be surrendered for payment of the redemption price.

(i)    PARTIAL REDEMPTION. In case of any redemption of only part of the Series B Preference Shares at the time outstanding, the Series B Preference Shares to be redeemed shall be selected pro rata or by lot, in accordance with the procedures of DTC.

(j)    RESTRICTIONS ON REDEMPTION. Under Bermuda law, the Company may not lawfully redeem Preference Shares (including the Series B Preference Shares) if on the date redemption is to be effected there are reasonable grounds for believing that the Company is, or after the redemption would be, unable to pay its liabilities as they become due, or that the Company is, or after such redemption would be, in breach of the Insurance Act, the Insurance (Eligible Capital) Rules 2012, the Group Solvency Standards, including Enhanced Capital Requirements, or such other Applicable Supervisory Regulations. Preference Shares (including the Series B Preference Shares) may not be redeemed except out of the capital paid up thereon, out of funds of the Company that would otherwise be available for dividends or distributions or out of the proceeds of a new issue of shares made for the purpose of the redemption. The premium, if any, payable on redemption must be provided for out of funds of the Company that would otherwise be available for dividend or distribution or out of the Company’s share premium account before the Series B Preference Shares are redeemed or purchased.

Unless full cumulative dividends on all issued Series B Preference Shares and all Parity Shares shall have been declared and paid (or declared and a sum sufficient for the payment thereof set aside for payment) for all past Dividend Periods, no Series B Preference Shares or any Parity Shares may be redeemed, purchased or otherwise acquired by the Company unless all issued Series B Preference Shares and any Parity Shares are redeemed; provided that the Company may acquire fewer than all of the issued Series B Preference Shares or Parity Shares pursuant to a purchase or exchange offer made to all holders of issued Series B Preference Shares and Parity Shares upon such terms as the Board of Directors in its sole discretion after consideration of the respective annual dividend rate and other relative rights and preferences of the respective classes or series, will determine (which determination will be final and conclusive) will result in fair and equitable treatment among the respective classes or series; provided, further that the Series A Preference Shares may be forfeited, issued and converted into Common Shares in accordance with the terms of the Series A Preference Shares.

SECTION 8.    SUBSTITUTION OR VARIATION.

(a)    At any time following a Tax Event or at any time following a Capital Disqualification Event, the Company may, without the consent of any holders of the Series B Preference Shares, vary the terms of the Series B Preference Shares such that they remain securities, or exchange the Series B Preference Shares with new securities, which (i) in the case of a Tax Event, would eliminate the substantial probability that the Company or any Successor

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Company would be required to pay any additional amounts with respect to the Series B Preference Shares or (ii) in the case of a Capital Disqualification Event, would cause the Series B Preference Shares to become securities that qualify as at least Tier 2 capital, where capital is subdivided into tiers or its equivalent under then-applicable Capital Adequacy Regulations imposed upon us by the Applicable Supervisor, including the Enhanced Capital Requirement, for purposes of determining the solvency margin, capital adequacy ratios or any other comparable ratios, regulatory capital resource or level of the Company or any subsidiary thereof. In either case, the terms of the varied securities or new securities considered in the aggregate cannot be less favorable to holders than the terms of the Series B Preference Shares prior to being varied or exchanged; provided that no such variation of terms or securities received in exchange shall change the specified denominations of, dividend payable on, the Redemption Dates (other than any extension of the period during which an optional redemption may not be exercised by the Company) or currency of, the Series B Preference Shares, reduce the liquidation preference thereof, lower the ranking in right of payment with respect to the payment of dividends or the distribution of assets upon liquidation, dissolution or winding-up of the Series B Preference Shares, or change the foregoing list of items that may not be so amended as part of such substitution or variation. Further, no such variation of terms or securities received in exchange shall impair the right of a holder of the securities to institute suit for the payment of any amounts due (as provided under this Certificate of Designations), but unpaid with respect to such holder’s securities.

(b)    Prior to any substitution or variation, the Company shall be required to deliver a certificate signed by two executive officers of the Company to the transfer agent for the Series B Preference Shares confirming that (x) a Capital Disqualification Event or a Tax Event has occurred and is continuing (as reasonably determined by the Company) and (y) the terms of the varied or new securities, considered in the aggregate, are not less favorable, including from a financial perspective, to holders and beneficial owners of the Series B Preference Shares than the terms of the Series B Preference Shares prior to being varied or exchanged (as reasonably determined by the Company).

(c)    Any substitution or variation of the Series B Preference Shares described above shall be made after notice is given to the holders of the Series B Preference Shares not less than 15 days nor more than 60 days prior to the date fixed for substitution or variation, as applicable.

SECTION 9.    VOTING RIGHTS.

(a)    GENERAL. The holders of Series B Preference Shares shall not have any voting rights except as set forth below or as otherwise from time to time required by law. On any item on which the holders of the Series B Preference Shares are entitled to vote, such holders shall be entitled to one vote for each Series B Preference Share held.

(b)    RIGHT TO ELECT TWO DIRECTORS UPON NONPAYMENT EVENTS. If and whenever dividends in respect of any Series B Preference Shares shall have not been declared and paid, on a cumulative basis, for the equivalent of six or more Dividend Periods, whether or not consecutive (a “Nonpayment Event”), the holders of Series B Preference Shares, voting together as a single class with the holders of any and all Voting Preference Shares then outstanding, shall be entitled to vote for the election of a total of two additional members of the

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Board of Directors (the “Preference Shares Directors”); provided that it shall be a qualification for election for any such Preference Shares Director that the election of any such directors shall not cause the Company to violate the corporate governance requirements of the U.S. Securities and Exchange Commission or the New York Stock Exchange (or any other securities exchange or other trading facility on which securities of the Company may then be listed or quoted) that listed or quoted companies must have a majority of independent directors. The Company shall use its best efforts to increase the number of directors constituting the Board of Directors to the extent necessary to effectuate such right, and, if necessary, to amend the Bye-Laws. Each Preference Shares Director shall be added to an already existing class of directors.

In the event that the holders of the Series B Preference Shares, and any such other holders of Voting Preference Shares, shall be entitled to vote for the election of the Preference Shares Directors following a Nonpayment Event, such directors shall be initially elected following such Nonpayment Event only at a special general meeting, or at any annual general meeting of shareholders, and thereafter at the annual general meeting of shareholders. At any time when such special voting power has vested in the holders of any of the Series B Preference Shares and any such other holders of Voting Preference Shares as described above, the chief executive officer of the Company shall, upon the written request of the holders of record of at least 10% of the aggregate liquidation preference of the Series B Preference Shares and Voting Preference Shares (taken together as a single class) then outstanding addressed to the secretary of the Company, call a special general meeting of the holders of the Series B Preference Shares and Voting Preference Shares for the purpose of electing directors. Such meeting shall be held at the earliest practicable date in such place as may be designated pursuant to the Bye-Laws (or if there be no designation, at the Company’s principal office in Bermuda). If such meeting shall not be called by the Company’s proper officers within 20 days after the Company’s secretary has been personally served with such request, or within 60 days after mailing the same by registered or certified mail addressed to the Company’s secretary at the Company’s principal office, then the holders of record of at least 10% of the aggregate liquidation preference of the Series B Preference Shares and Voting Preference Shares (taken together as a single class) then outstanding may designate in writing one such holder to call such meeting at the Company’s expense, and such meeting may be called by such holder so designated upon the notice required for annual general meetings of shareholders and shall be held in Bermuda, unless the Company otherwise designates.

Notwithstanding the foregoing, no such special general meeting shall be called during the period within 60 days immediately preceding the date fixed for the next annual general meeting of shareholders.

At any annual or special general meeting at which the holders of the Series B Preference Shares and any such other holders of Voting Preference Shares shall be entitled to vote, voting together as a single class, for the election of the Preference Shares Directors following a Nonpayment Event, the presence, in person or by proxy, of the holders of 50% of the aggregate liquidation preference of such Series B Preference Shares and Voting Preference Shares (taken together as a single class) shall be required to constitute a quorum of the Series B Preference Shares and Voting Preference Shares (taken together as a single class) for the election of any director by the holders of the Series B Preference Shares and Voting Preference Shares (taken together as a single class). At any such meeting or adjournment thereof, the absence of a quorum of

15

the Series B Preference Shares and Voting Preference Shares shall not prevent the election of directors other than those to be elected by the Series B Preference Shares and Voting Preference Shares, voting together as a single class, and the absence of a quorum for the election of such other directors shall not prevent the election of the directors to be elected by the Series B Preference Shares and Voting Preference Shares, voting together as a single class.

The Preference Shares Directors so elected by the holders of the Series B Preference Shares and Voting Preference Shares shall continue in office (i) until their successors, if any, are elected by such holders or (ii) unless required by applicable law to continue in office for a longer period, until termination of the right of the holders of the Series B Preference Shares and Voting Preference Shares to vote as a class for directors, if earlier. If and to the extent permitted by applicable law, immediately upon any termination of the right of the holders of the Series B Preference Shares and Voting Preference Shares to vote together as a single class for directors as provided herein, the terms of office of the directors then in office so elected by the holders of the Series B Preference Shares and Voting Preference Shares shall terminate.

When all accrued and unpaid dividends in respect of all prior completed Dividend Periods have been paid in full on the Series B Preference Shares for at least four consecutive Dividend Periods after a Nonpayment Event, then the holders of the Series B Preference Shares shall be divested of the right to elect the Preference Shares Directors (subject to revesting of such voting rights in the event of each subsequent Nonpayment Event pursuant to this Section 9) and the number of Dividend Periods in which dividends have not been declared and paid shall be reset to zero, and if and when the rights of holders of Voting Preference Shares to elect the Preference Shares Directors shall have ceased, the terms of office of all the Preference Shares Directors shall forthwith terminate and the number of directors constituting the Board of Directors shall automatically be reduced accordingly. For purposes of determining whether dividends have been paid for four consecutive Dividend Periods following a Nonpayment Event, the Company may take account of any dividend it elects to pay for such a Dividend Period after the Dividend Payment Date for such Dividend Period has passed.

Any Preference Shares Director may be removed at any time without cause by the holders of record of a majority of the aggregate voting power, as determined under the Bye-Laws, of Series B Preference Shares and any other shares of Voting Preference Shares then outstanding (voting together as a single class) when they have the voting rights described above. Until the right of the holders of Series B Preference Shares and any Voting Preference Shares to elect the Preference Shares Directors shall cease, any vacancy in the office of a Preference Shares Director (other than prior to the initial election of Preference Shares Directors after a Nonpayment Event) may be filled by the written consent of the Preference Shares Director remaining in office, or if none remain in office, by a vote of the holders of record of a majority of the aggregate liquidation preference of the outstanding Series B Preference Shares and any other shares of Voting Preference Shares (voting together as a single class) when they have the voting rights described above. Any such vote of holders of Series B Preference Shares and Voting Preference Shares to remove, or to fill a vacancy in the office of, a Preference Shares Director may be taken only at a special meeting of such shareholders, called as provided above for an initial election of Preference Shares Directors after a Nonpayment Event (unless such request is received less than 60 days before the date fixed for the next annual or special meeting of the shareholders of the Company, in which event such election

16

shall be held at such next annual or special meeting of shareholders). The Preference Shares Directors shall each be entitled to one vote per director on any matter. Each Preference Shares Director elected at any special general meeting of shareholders of the Company or by written consent of the other Preference Shares Director shall hold office until the next annual general meeting of the shareholders of the Company if such office shall not have previously terminated as above provided.

(c)    CHANGES AFTER PROVISION FOR REDEMPTION. No vote or consent of the holders of Series B Preference Shares shall be required pursuant to Section 9(b) or (e) if, at or prior to the time when the act with respect to which such vote would otherwise be required pursuant to such Section shall be effected, all outstanding Series B Preference Shares shall have been redeemed, or shall have been called for redemption upon proper notice and sufficient funds shall have been set aside by the Company for such redemption, in each case pursuant to Section 7 herein.

(d)    PROCEDURES FOR VOTING AND CONSENTS. The rules and procedures for calling and conducting any meeting of the holders of Series B Preference Shares (including, without limitation, the fixing of a record date in connection therewith), the solicitation and use of proxies at such a meeting, the obtaining of written consents and any other aspect or matter with regard to such a meeting or such consents shall be governed by any rules the Board of Directors or a duly authorized committee of the Board of Directors, in its discretion, may adopt from time to time, which rules and procedures shall conform to the requirements of the Bye-Laws, applicable law and any national securities exchange or other trading facility on which the Series B Preference Shares is listed or traded at the time. Whether the vote or consent of the holders of a plurality, majority or other portion of the Series B Preference Shares and any Voting Preference Shares has been cast or given on any matter on which the holders of Series B Preference Shares are entitled to vote shall be determined by the Company by reference to the aggregate voting power, as determined by the Bye-Laws of the Company, of the shares voted or covered by the consent.

(e)    VOTING ON VARIATIONS OF RIGHTS AND SENIOR SHARES.

(1)    Notwithstanding the Bye-Laws, the affirmative vote or consent of the holders of at least 66 2/3% of the aggregate liquidation preference of the Series B Preference Shares and any other shares of Voting Preference Shares then outstanding (voting together as a single class) shall be required for the authorization or issuance of any class or series of Senior Shares (or any security convertible into or exchangeable for Senior Shares) ranking senior to the Series B Preference Shares as to dividend rights or rights upon the Company’s liquidation.

(2)    The affirmative vote or consent of the holders of at least 66 2/3% of the aggregate liquidation preference of the Series B Preference Shares then outstanding shall be required for amendments to the Company’s Memorandum of Association or Bye-Laws that would materially adversely affect the rights of holders of the Series B Preference Shares.

SECTION 10.    RANKING. The Series B Preference Shares shall, with respect to the payment of dividends and distributions of assets upon liquidation, dissolution and winding-up, rank

17

senior to Junior Shares, junior to any Senior Shares and pari passu with any Parity Shares of the Company, including those that the Company may issue from time to time in the future.

SECTION 11.    RECORD HOLDERS. To the fullest extent permitted by applicable law, the Company and the transfer agent for the Series B Preference Shares may deem and treat the record holder of any Series B Preference Share as the true and lawful owner thereof for all purposes, and neither the Company nor such transfer agent shall be affected by any notice to the contrary.

SECTION 12.    NOTICES. All notices or communications in respect of Series B Preference Shares shall be sufficiently given if given in writing and delivered in person or by first class mail, postage prepaid, or if given in such other manner as may be permitted in this Certificate of Designations, Bye-Laws or by applicable law. Notwithstanding the foregoing, if Series B Preference Shares or depositary shares representing an interest in Series B Preference Shares are issued in book-entry form through DTC, such notices may be given to the holders of the Series B Preference Shares in any manner permitted by DTC.

SECTION 13.    NO CONVERSION RIGHTS. The Series B Preference Shares are not convertible into or exchangeable for any other securities or property of the Company, except under the circumstances set forth under Section 8(a).

SECTION 14.    NO PREEMPTIVE RIGHTS. No Series B Preference Share shall have any rights of preemption whatsoever as to any securities of the Company, or any warrants, rights or options issued or granted with respect thereto, regardless of how such securities, or such warrants, rights or options, may be designated, issued or granted.

SECTION 15.    OTHER RIGHTS. The Series B Preference Shares shall not have any voting powers, preferences or relative, participating, optional or other special rights, or qualifications, limitations or restrictions thereof, other than as set forth herein or in the Bye-Laws or as provided by applicable law.

SECTION 16.    CERTIFICATES. The Company may, at its option, issue shares of Series B Preference Shares without certificates. As long as DTC or its nominee is the registered owner of the Series B Preference Shares, DTC or its nominee, as the case may be, will be considered the sole owner and holder of all Series B Preference Shares. If DTC discontinues providing its services as securities depositary with respect to the Series B Preference Shares, or if DTC ceases to be ceases to be registered as a clearing agency under the Exchange Act, in the event that a successor securities depositary is not obtained within 90 days, the Company will either print and deliver certificates for the Series B Preference Shares or provide for the direct registration of the Series B Preference Shares with the transfer agent. If the Company decides to discontinue the use of the system of book-entry-only transfers through DTC (or a successor securities depositary), certificates for the Series B Preference Shares will be printed and delivered to DTC or the Company will provide for the direct registration of the Series B Preference Shares with the transfer agent. Except in the limited circumstances referred to above, owners of beneficial interests in the Series B Preference Shares:

18

(a)    will not be entitled to have such Series B Preference Shares registered in their names;

(b)    will not receive or be entitled to receive physical delivery of securities certificates in exchange for beneficial interests in the Series B Preference Shares; and

(c)    will not be considered to be owners or holders of the Series B Preference Shares for any purpose under the instruments governing the rights and obligations of holders of the Series B Preference Shares.

SECTION 17.    STOCK EXCHANGE LISTING. The Company shall use reasonable best efforts to cause the Series B Preference Shares to be listed on the New York Stock Exchange as soon as possible following the Issue Date, but in no event later than [●], 202[●]5, and to maintain such listing for so long as any Series B Preference Shares remain outstanding, at the Company’s sole expense.

[Signature Page Follows]

IN WITNESS WHEREOF, SiriusPoint Ltd. has caused this certificate to be signed by [●], its [●] as of this ___ day of _______, 202__.

SIRIUSPOINT LTD.

By:            

Name:     [●]

Title:     [●]

5NTD: To be the date that is 120 days from the Issue Date.

19

IN WITNESS WHEREOF, SiriusPoint Ltd. has caused this certificate to be signed by [●], its [●] as of this ___ day of _______, 202__.

SIRIUSPOINT LTD.

By:

Name:     [●]

Title:     [●]

[Signature Page to Certificate of Designations]

20

XML

Cover Page - shares	9 Months Ended
	Sep. 30, 2020	Oct. 31, 2020
Cover [Abstract]
Document Type	10-Q
Document Quarterly Report	true
Document Period End Date	Sep. 30, 2020
Document Transition Report	false
Entity File Number	001-38731
Entity Registrant Name	SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.
Entity Incorporation, State or Country Code	D0
Entity Tax Identification Number	98-0529995
Entity Address, Address Line One	14 Wesley Street
Entity Address, City or Town	Hamilton
Entity Address, Postal Zip Code	HM 11
Entity Address, Country	BM
City Area Code	441
Local Phone Number	278-3140
Title of 12(b) Security	Common shares, par value $0.01 per share
Trading Symbol	SG
Security Exchange Name	NASDAQ
Entity Current Reporting Status	Yes
Entity Interactive Data Current	Yes
Entity Filer Category	Non-accelerated Filer
Entity Small Business	true
Entity Emerging Growth Company	false
Entity Shell Company	false
Entity Common Stock, Shares Outstanding		115,299,341
Entity Central Index Key	0001744894
Amendment Flag	false
Current Fiscal Year End Date	--12-31
Document Fiscal Year Focus	2020
Document Fiscal Period Focus	Q3

XML

Consolidated Balance Sheets - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Assets
Fixed maturity investments, trading, at fair value (Amortized cost 2020: $1,932.7; 2019: $1,656.6)	$ 1,958.9	$ 1,681.0
Short-term investments, at fair value (Amortized cost 2020: $1,145.4; 2019: $1,090.8)	1,132.6	1,085.2
Equity securities, trading, at fair value (Cost 2020: $170.0; 2019: $379.2)	158.7	405.2
Other long-term investments, at fair value (Cost 2020: $327.5; 2019: $315.4)	388.0	346.8
Cash	168.4	136.3
Restricted cash	15.8	14.3
Total investments and cash	3,822.4	3,668.8
Accrued investment income	8.9	11.2
Insurance and reinsurance premiums receivable	789.0	730.1
Reinsurance recoverable on unpaid losses	482.5	410.3
Reinsurance recoverable on paid losses	70.4	73.9
Funds held by ceding companies	244.1	293.9
Ceded unearned insurance and reinsurance premiums	172.5	162.0
Deferred acquisition costs	145.2	148.2
Deferred tax asset	158.4	166.7
Accounts receivable on unsettled investment sales	19.1	6.7
Goodwill	400.8	400.8
Intangible assets	168.0	179.8
Other assets	151.5	161.4
Total assets	6,632.8	6,413.8
Liabilities
Loss and loss adjustment expense reserves	2,672.9	2,331.5
Unearned insurance and reinsurance premiums	759.4	708.0
Ceded reinsurance payable	270.3	244.7
Funds held under reinsurance treaties	156.5	169.1
Deferred tax liability	213.6	205.9
Debt	695.8	685.2
Accounts payable on unsettled investment purchases	29.9	2.3
Other liabilities	175.9	201.3
Total liabilities	4,974.3	4,548.0
Commitments and contingencies (see Note 19)
Mezzanine equity
Series B preference shares	197.5	223.0
Common shareholders' equity
Common shares (shares issued and outstanding, 2020 & 2019: 115,299,341)	1.2	1.2
Additional paid-in surplus	1,099.9	1,098.2
Retained earnings	564.5	778.5
Accumulated other comprehensive (loss)	(206.4)	(237.5)
Total common shareholders' equity	1,459.2	1,640.4
Non-controlling interests	1.8	2.4
Total equity	1,461.0	1,642.8
Total liabilities, mezzanine equity, and equity	$ 6,632.8	$ 6,413.8

XML

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Statement of Financial Position [Abstract]
Fixed maturity investments, trading, amortized cost	$ 1,932.7	$ 1,656.6
Short-term investments, amortized cost	1,145.4	1,090.8
Equity securities, at cost	170.0	379.2
Other long-term investments, cost	$ 327.5	$ 315.4
Shares issued (in shares)	115,299,341	115,299,341
Shares outstanding (in shares)	115,299,341	115,299,341

XML

Consolidated Statements of (Loss) Income - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Revenues
Net earned insurance and reinsurance premiums	$ 372.6	$ 374.2	$ 1,177.1	$ 1,056.8
Net investment income	1.7	22.8	30.0	67.3
Net realized investment (losses) gains	(3.8)	15.3	23.6	39.9
Net unrealized investment gains (losses)	31.2	53.9	(3.9)	143.4
Net foreign exchange (losses) gains	(21.3)	4.9	(18.9)	9.4
Other revenue	15.8	16.3	30.3	51.3
Total revenues	396.2	487.4	1,238.2	1,368.1
Expenses
Loss and loss adjustment expenses	305.4	348.6	972.8	810.5
Insurance and reinsurance acquisition expenses	83.6	75.1	236.4	215.4
Other underwriting expenses	41.3	35.4	115.6	106.2
General and administrative expenses	34.4	28.0	90.4	80.6
Intangible asset amortization expenses	3.9	3.9	11.8	11.8
Interest expense on debt	8.1	7.7	23.8	23.3
Total expenses	476.7	498.7	1,450.8	1,247.8
Pre-tax income (loss)	(80.5)	(11.3)	(212.6)	120.3
Income tax (expense) benefit	(23.5)	3.7	(19.9)	(15.6)
Net (loss) income	(104.0)	(7.6)	(232.5)	104.7
Loss (income) attributable to non-controlling interests	(0.2)	(0.4)	(0.2)	(1.6)
(Loss) income attributable to Sirius Group	(104.2)	(8.0)	(232.7)	103.1
Change in carrying value of Series B preference shares	8.7	5.3	25.5	(3.9)
Net (loss) income attributable to Sirius Group's common shareholders	$ (95.5)	$ (2.7)	$ (207.2)	$ 99.2
Net (loss) income per common share and common share equivalent
Basic earnings per common share and common share equivalent (in dollars per share)	$ (0.83)	$ (0.02)	$ (1.80)	$ 0.78
Diluted earnings per common share and common share equivalent (in dollars per share)	$ (0.83)	$ (0.06)	$ (1.83)	$ 0.78
Weighted average number of common shares and common share equivalents outstanding:
Basic weighted average number of common shares and common share equivalents outstanding (in shares)	115,297,945	115,251,853	115,279,197	115,225,942
Diluted weighted average number of common shares and common share equivalents outstanding (in shares)	115,297,945	127,153,523	127,180,867	115,619,222

XML

Consolidated Statements of Comprehensive (Loss) Income - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Comprehensive (loss) income
Net (loss) income	$ (104.0)	$ (7.6)	$ (232.5)	$ 104.7
Other comprehensive income (loss)
Change in foreign currency translation, net of tax	37.5	(42.3)	31.1	(69.0)
Total other comprehensive income (loss)	37.5	(42.3)	31.1	(69.0)
Comprehensive (loss) income	(66.5)	(49.9)	(201.4)	35.7
Net (income) attributable to non-controlling interests	(0.2)	(0.4)	(0.2)	(1.6)
Comprehensive (loss) income attributable to Sirius Group	$ (66.7)	$ (50.3)	$ (201.6)	$ 34.1

XML

Consolidated Statements of Shareholders' Equity - USD ($) $ in Millions	Total	Common shares	Additional paid-in surplus	Retained earnings	Accumulated other comprehensive (loss)	Parent	Non-controlling interests	Cumulative effect, period of adoption Retained earnings	Adjusted balance Retained earnings
Beginning balance at Dec. 31, 2018		$ 1.2	$ 1,089.1	$ 816.6	$ (202.4)				$ 816.6
Changes in common shareholders' equity
Share-based compensation			7.9
Net (loss) income	$ 104.7			104.7
Loss (income) attributable to non-controlling interests	(1.6)			(1.6)
Change in carrying value of Series B preference shares				(3.9)
Net change in foreign currency translation	(69.0)				(69.0)
Ending balance at Sep. 30, 2019	1,746.0		1,097.0	915.8	(271.4)	$ 1,742.6	$ 3.4
Beginning balance at Jun. 30, 2019		1.2	1,093.5	918.5	(229.1)				918.5
Changes in common shareholders' equity
Share-based compensation			3.4
Other, net			0.1
Net (loss) income	(7.6)			(7.6)
Loss (income) attributable to non-controlling interests	(0.4)			(0.4)
Change in carrying value of Series B preference shares				5.3
Net change in foreign currency translation	(42.3)				(42.3)
Ending balance at Sep. 30, 2019	1,746.0		1,097.0	915.8	(271.4)	1,742.6	3.4
Beginning balance at Dec. 31, 2019	1,642.8	1.2	1,098.2	778.5	(237.5)			$ (6.8)	771.7
Changes in common shareholders' equity
Share-based compensation			1.7
Net (loss) income	(232.5)			(232.5)
Loss (income) attributable to non-controlling interests	(0.2)			(0.2)
Change in carrying value of Series B preference shares				25.5
Net change in foreign currency translation	31.1				31.1
Ending balance at Sep. 30, 2020	1,461.0		1,099.9	564.5	(206.4)	1,459.2	1.8
Beginning balance at Jun. 30, 2020		$ 1.2	1,102.4	660.0	(243.9)				$ 660.0
Changes in common shareholders' equity
Share-based compensation			(2.5)
Net (loss) income	(104.0)			(104.0)
Loss (income) attributable to non-controlling interests	(0.2)			(0.2)
Change in carrying value of Series B preference shares				8.7
Net change in foreign currency translation	37.5				37.5
Ending balance at Sep. 30, 2020	$ 1,461.0		$ 1,099.9	$ 564.5	$ (206.4)	$ 1,459.2	$ 1.8

XML

Consolidated Statements of Cash Flows - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019
Cash flows from operating activities:
Net (loss) income	$ (232.5)	$ 104.7
Adjustments to reconcile net income to net cash provided from operations:
Net realized and unrealized investment losses (gains)	(19.7)	(183.3)
Amortization of premium on fixed maturity investments	3.8	(4.7)
Amortization of intangible assets	11.8	11.8
Depreciation and other amortization	5.0	6.3
Share-based compensation	1.7	7.9
Revaluation of contingent consideration	0.6	0.0
Net gain on sale of consolidated affiliate	(0.9)	0.0
Other operating items:
Net change in loss and loss adjustment expense reserves	296.8	274.1
Net change in reinsurance recoverable on paid and unpaid losses	(46.1)	(82.0)
Net change in funds held by ceding companies	54.3	(61.5)
Net change in unearned insurance and reinsurance premiums	24.0	212.4
Net change in ceded reinsurance payable	9.7	73.3
Net change in ceded unearned insurance and reinsurance premiums	0.5	(32.4)
Net change in insurance and reinsurance premiums receivable	(30.7)	(269.4)
Net change in deferred acquisition costs	6.4	(22.5)
Net change in funds held under reinsurance treaties	(15.7)	33.1
Net change in current and deferred income taxes, net	21.1	(4.8)
Net change in other assets and liabilities, net	25.4	24.9
Net cash provided from operating activities	115.5	87.9
Cash flows from investing activities:
Net change in short-term investments	(5.5)	(285.8)
Sales of fixed maturities and convertible fixed maturity investments	380.6	430.7
Maturities, calls, and paydowns of fixed maturity and convertible fixed maturity investments	223.5	239.4
Sales of common equity securities	858.5	212.6
Distributions, redemptions, and maturities of other long-term investments	22.8	53.6
Return of principal on loan participations	1.4	0.0
Sale of consolidated affiliate, net of cash sold	11.2	0.0
Contributions to other long-term investments	(30.5)	(46.5)
Purchases of common equity securities	(653.3)	(174.9)
Purchases of fixed maturities and convertible fixed maturity investments	(870.2)	(504.4)
Purchases of loan participation	(10.0)	0.0
Net change in unsettled investment purchases and sales	15.4	23.7
Other, net	(2.5)	0.8
Net cash (used for) investing activities	(58.6)	(50.8)
Cash flows from financing activities:
Payment of contingent consideration	(28.4)	0.0
Cash dividends paid to non-controlling interests	(1.0)	0.0
Change in collateral held on Interest Rate Cap	0.0	(0.1)
Net cash (used for) financing activities	(29.4)	(0.1)
Effect of exchange rate changes on cash	6.1	(9.4)
Net increase (decrease) in cash during period	33.6	27.6
Cash, restricted cash, and cash held for sale balance at beginning of period	150.6	132.2
Cash, restricted cash, and cash held for sale balance at end of period	$ 184.2	$ 159.8

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General	9 Months Ended
	Sep. 30, 2020
Organization, Consolidation and Presentation of Financial Statements [Abstract]
General	GeneralSirius International Insurance Group, Ltd. ("the Company") is a Bermuda exempted company that provides multi-line insurance and reinsurance on a worldwide basis through its subsidiaries (collectively with the Company, "Sirius Group").

XML

Summary of significant accounting policies

9 Months Ended

Sep. 30, 2020

Accounting Policies [Abstract]

Summary of significant accounting policies

Summary of significant accounting policies

Basis of presentation

The accompanying Unaudited Consolidated Financial Statements at September 30, 2020, have been prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP") and the rules and regulations of the U.S. Securities and Exchange Commission ("SEC") for interim financial information. The accompanying Unaudited Consolidated Financial Statements present the consolidated results of operations, financial condition, and cash flows of the Company and its subsidiaries and those entities in which the Company has control and a majority economic interest as well as those variable interest entities ("VIEs") that meet the requirements for consolidation. All significant intercompany transactions have been eliminated in consolidation.

These Unaudited Consolidated Financial Statements do not include all disclosures normally included in annual financial statements prepared in accordance with GAAP and should be read in conjunction with the Audited Consolidated Financial Statements and the related notes for the year ended December 31, 2019. The consolidated financial information as of December 31, 2019 included herein has been derived from the Audited Consolidated Financial Statements as of December 31, 2019.

Effective January 1, 2020, the Company changed its reportable segments. The change in reportable segments had no impact on the Company’s historical consolidated financial positions, results of operations or cash flows as previously reported. Where applicable, all prior periods presented have been revised to conform to this new presentation.

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities as of the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. In the opinion of management, the accompanying Unaudited Consolidated Financial Statements reflect all adjustments (consisting of normally recurring accruals) necessary for a fair statement of results on an interim basis. Tabular dollar amounts are in millions, with the exception of share and per share amounts. All amounts are reported in U.S. dollars, except where noted otherwise.

Recently adopted changes in accounting principles

Credit losses

Effective January 1, 2020, Sirius Group adopted Accounting Standards Update ("ASU") 2016-13, Measurement of Credit Losses on Financial Instruments (ASC 326), which establishes new guidance for the recognition of credit losses for financial assets measured at amortized cost ("current expected credit losses" or "CECL"). The guidance applies to financial assets that have the contractual right to receive cash, including reinsurance receivables and recoverables and requires reporting entities to estimate the credit losses expected over the life of a credit exposure using historical information, current information and reasonable and supportable forecasts that affect the collectability of the financial asset. The expected credit losses, and subsequent adjustments to such losses, are recorded through an allowance account that is deducted from the amortized cost basis of the financial asset, with the net carrying value of the financial asset presented on the consolidated balance sheet at the amount expected to be collected. Sirius Group adopted the new guidance using a modified retrospective transition method through a cumulative-effect adjustment to retained earnings.

As a result of the adoption of the new guidance, Sirius Group estimated a total CECL allowance of $14.9 million. The adoption of this guidance did not materially impact our results of operations or cash flows. Due to the adoption of the standard using the retrospective cumulative-effect adjustment method, the Company recorded a $(6.8) million cumulative-effect adjustment net of taxes to its opening retained earnings. (See Note 7.)

Fair Value Measurement Disclosures

Effective January 1, 2020, Sirius Group adopted ASU 2018-13, Fair Value Measurement (Topic 820): Disclosure Framework—Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements of fair value measurements. The adoption of this guidance did not have any impact on the consolidated financial statements but expanded disclosure of the ranges and weighted averages of significant unobservable inputs used in Level 3 fair values. (See Note 9.)

Simplifying the Accounting for Income Taxes

Effective January 1, 2020, Sirius Group adopted ASU 2019-12, Income Taxes (Topic 740): Simplifying the Accounting for Income Taxes, which eliminates certain exceptions, and clarifies and simplifies certain aspects of accounting for income taxes. Sirius Group has fully adopted all provisions of the guidance with consideration of the various transition methods.

Sirius Group adopted the removal of the exception to the general methodology for calculating income taxes in an interim period when a year-to-date loss exceeds the anticipated loss for the year. The removal of this exception allowed Sirius Group to record a benefit for a year-to-date loss in excess of its forecasted loss in certain jurisdictions. The removal of this exception was applied prospectively to the Income tax benefit (expense) line on the Consolidated Statements of (Loss) Income.

Sirius Group adopted all other provisions in the guidance, including the requirement for an entity to recognize a franchise tax (or similar tax) that is partially based on income as an income-based tax and account for any incremental amount incurred as a non-income-based tax through a cumulative-effect adjustment to retained earnings. These provisions did not have a material impact on the Consolidated Financial Statements or were not applicable to Sirius Group.

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Significant transactions

9 Months Ended

Sep. 30, 2020

Discontinued Operations and Disposal Groups [Abstract]

Significant transactions

Significant transactions

Merger Agreement with Third Point Reinsurance, Ltd.

On August 6, 2020, the Company announced that it had entered into an Agreement and Plan of Merger (the “Merger Agreement”), by and among the Company, Third Point Reinsurance Ltd., a Bermuda exempted company (“TPRE”), and Yoga Merger Sub Limited, a Bermuda exempted company and a wholly owned subsidiary of TPRE (“Merger Sub”). The Merger Agreement provides, among other things, that, upon the terms and subject to the conditions set forth in the Merger Agreement and a Statutory Merger Agreement to be executed by the Company, TPRE and Merger Sub (the “Statutory Merger Agreement”), Merger Sub will merge with and into the Company, with the Company surviving as a wholly owned subsidiary of TPRE (the “Merger”). The Merger Agreement, the Statutory Merger Agreement, and the consummation of the transactions contemplated by the Merger Agreement and the Statutory Merger Agreement, including the Merger (the “Transactions”), have been unanimously approved by the board of directors of each of the Company and TPRE. The consummation of the Transactions is expected to occur during the first quarter of 2021, subject to the satisfaction or waiver of applicable closing conditions.

Under the terms of the Merger Agreement, as of the effective time of the Merger, each issued and outstanding common share, par value $0.01 per share, of the Company (“Company Shares”) will be converted into the right to receive, at the election of the holder thereof, (i) $9.50 in cash, or (ii) (A) 0.743 of a common share, par value $0.10 per share, of TPRE (“TPRE Shares”) and (B) one contractual contingent value right (each, a “CVR”), which will represent the right to receive a contingent cash payment, and which, taken together with the fraction of the TPRE Share received, guarantee that on the second anniversary of the closing date of the Merger, the electing shareholder will have received equity and cash with a value of at least $13.73 per share (the “Share & CVR Election”), or (iii) (A) $0.905 in cash, (B) a number of TPRE Shares equal to the Mixed Election Common Shares Exchange Ratio (as such term is defined in the Merger Agreement), (C) a number of newly issued Series A preference shares of TPRE (“TPRE Preference Shares”) equal to the Mixed Election Preference Shares Exchange Ratio (as such term is defined in the Merger Agreement), (D) 0.190 of a warrant issued by TPRE and (E) $0.905 aggregate principal amount of a right issued by TPRE (the “Mixed Election”). Elections must be made no later than ten (10) Business Days (as defined in the Merger Agreement) prior to the closing of the Transactions. Pursuant to the Voting and Support Agreement dated August 6, 2020 among CM Bermuda Limited ("CM Bermuda"), CMIG International Holding Pte. Ltd. (“CMIG International”), the Company and TPRE, CM Bermuda, whose parent company is CMIG International, has agreed to make the Mixed Election. Holders of Company Shares who do not make an election will be deemed to have made the Share & CVR Election. No fractional TPRE Shares or TPRE Preference Shares will be issued in the Merger, and holders of Company Shares will receive cash in lieu of any fractional TPRE Shares or TPRE Preference Shares. Dissenting Company shareholders will be entitled to exercise appraisal rights under Bermuda law.

The consummation of the Merger is subject to the satisfaction or waiver of certain conditions, including, among others, (i) the affirmative vote in favor of the approval of the Merger Agreement, the Merger and the Statutory Merger Agreement by the holders of a majority of the voting power of the Company Shares and the Company’s Series B preference shares, voting together as a single class, that are present (in person or by proxy) at the Company shareholder meeting called for such purpose, (ii) the affirmative vote in favor of the approval of the issuance of TPRE Shares in the Merger as contemplated by the Merger Agreement (the “TPRE Share Issuance”) by the holders of at least a majority of the voting power of TPRE Shares that are present (in person or by proxy) at the TPRE shareholder meeting called for such purpose, (iii) the expiration or termination of any applicable waiting period (together with any extensions thereof) under the Hart-Scott-Rodino Antitrust Improvements Act of 1976 and any other applicable antitrust laws, (iv) the receipt of certain approvals under applicable insurance laws, (v) the absence of any effective order issued by any governmental authority or court of competent jurisdiction or other legal restraint prohibiting or preventing the consummation of the Merger, (vi) in the case of each party’s obligation to effect the Merger, the absence of a material adverse effect with respect to the other party and its subsidiaries, taken as a whole, since the date of the Merger Agreement, (vii) in the case of each party’s obligation to effect the Merger, subject to certain materiality exceptions, the accuracy of the representations and warranties made by the other party, and compliance by the other party in all material respects with such party’s respective obligations under the Merger Agreement and (viii) other customary closing conditions.

Sirius Group incurred various legal, advisory, and other consulting costs associated with the proposed Merger of $10 million, which are included in the Company's financial condition or results of operations as of and for the three and nine months ended September 30, 2020. As part of the amount incurred, $2.2 million is in connection with the Transaction Matters Letter Agreement entered into by Sirius Group, TPRE, CM Bermuda and CMIG International on August 6, 2020. (See Note 18.)

Empire Insurance Company

On July 7, 2020, Sirius Group sold 100% of the common shares of Empire Insurance Company (“Empire”) to Physicians' Reciprocal Insurers. Sirius Group received $11.4 million of proceeds and recognized a $0.9 million gain on the sale of Empire.

Loss portfolio transfer

On January 23, 2020, Sirius Group consummated a loss portfolio transfer with Pacific Re, Inc. Under the agreement, Sirius Group received $69.7 million in cash and assumed net undiscounted loss and loss adjustment expenses ("LAE") reserves with the same value. In addition, Sirius Group recognized Gross written premium and Loss and loss adjustment expenses for $69.7 million.

As part of closing on the loss portfolio transfer, an estimate of net paid losses was included. Sixty days after the closing, actual net paid losses were determined and Sirius Group paid back $0.4 million in cash to Pacific Re, Inc. and reduced assumed net undiscounted loss and LAE reserves by the same value. In addition, Sirius Group adjusted Gross written premium and Loss and loss adjustment expenses by $(0.4) million.

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Segment information

9 Months Ended

Sep. 30, 2020

Segment Reporting [Abstract]

Segment information

Segment information

On December 31, 2019, Sirius Group completed an internal reorganization and, beginning on January 1, 2020, Sirius Group's reportable segments consist of four reportable segments – Global Reinsurance, Global Accident & Health ("Global A&H"), U.S. Specialty, and Runoff & Other. The accounting policies of the reportable segments are the same as those used for the preparation of the Company's consolidated financial statements.

The Company's Global Reinsurance, Global A&H, U.S. Specialty, and Runoff & Other reportable segments each have managers who are responsible for the overall profitability of their respective segments and who are directly accountable to the Company's chief operating decision maker, the Chief Executive Officer ("CEO") of the Company. The CEO assesses segment operating performance, allocates capital, and makes resource allocation decisions based on Technical income (loss), Underwriting income (loss), and Underwriting profit (loss), including net service fee revenue.

Segment results are shown prior to corporate eliminations. Corporate eliminations are shown to reconcile to consolidated Technical profit (loss), consolidated Underwriting income (loss) and consolidated Underwriting income (loss), including net service fee revenue.

Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets, and, accordingly, investment income is not allocated to each segment. The internal reorganization had no impact to the allocation of goodwill and intangible assets to the Global A&H segment. Where applicable, all prior periods presented have been revised to conform to this new presentation.

Global Reinsurance

Global Reinsurance consists of Sirius Group's underwriting lines of business that offer Other Property, Property Catastrophe Excess Reinsurance, Agriculture Reinsurance, Aviation & Space, Marine & Energy, Trade Credit, Contingency, and Casualty Reinsurance:

Other Property—Sirius Group participates in the broker market for property reinsurance treaties written on a proportional and excess of loss basis. For Sirius Group's international business, the book consists of treaty, written on both a proportional and excess of loss basis, facultative, and primary business, primarily in Europe, Asia and Latin America. In the United States, the book predominantly centers on significant participations on proportional and excess of loss treaties mostly in the excess and surplus lines segment of the market.

Property Catastrophe Excess Reinsurance—Property catastrophe excess of loss reinsurance treaties cover losses from catastrophic events. Sirius Group writes a worldwide book with the largest concentration of exposure in Europe and the United States. The U.S. book written in Bermuda has a national account focus supporting principally the lower and/or middle layers of large capacity programs. Additionally, Stockholm writes a U.S. book mainly consisting of select small regional and standard lines carriers. The exposures written in the international book are diversified across many countries, regions, perils and layers.

Agriculture Reinsurance—Sirius Group provides stop-loss reinsurance coverage to companies writing U.S. government-sponsored multi-peril crop insurance ("MPCI"). Sirius Group's participation is net of the government's stop-loss reinsurance protection. Sirius Group also provides coverage for crop-hail and certain named perils when bundled with MPCI business. Sirius Group also writes agriculture business outside of the United States.

Aviation & Space—Sirius Group provides aviation insurance that covers loss of or damage to an aircraft and the aircraft operations' liability to passengers, cargo and hull as well as to third parties. Additionally, liability arising out of non-aircraft operations such as hangars, airports and aircraft products can be covered. Space insurance primarily covers loss of or damage to a satellite during launch and in orbit. The book consists of treaty, written on both a proportional and excess of loss basis, facultative, and primary business.

Marine & Energy—Sirius Group provides marine & energy reinsurance, primarily written on an excess of loss and proportional basis. Coverage offered includes damage to ships and goods in transit, marine liability lines, and offshore energy industry insurance. Sirius Group also writes yacht business, both on reinsurance and a primary basis. The marine & energy portfolio is diversified across many countries and regions.

Trade Credit—Sirius Group writes credit and bond reinsurance worldwide. The bulk of the business is traditional short-term commercial credit insurance, covering pre-agreed domestic and export sales of goods and services with typical coverage periods of 60 to 120 days. Losses under these policies are correlated to adverse changes in a respective country's gross national product.

Contingency—Sirius Group underwrote a contingency insurance book primarily for event cancellation and non-appearance.  Additionally, coverage for probability based risks with prize redemption was also offered. The contingency insurance business was exited in 2018; however, Sirius Group continues to offer this class on a treaty reinsurance basis on a selective basis for a few key clients.

Casualty Reinsurance—Sirius Group underwrites a cross section of all casualty lines, including general liability, umbrella, auto, workers compensation, professional liability, and other specialty classes, written on a proportional and excess of loss basis.

Global A&H

Global A&H consists of Sirius Group’s insurance and reinsurance business, and the managing general underwriting (“MGU”) units (which include ArmadaCorp Capital, LLC ("Armada") and International Medical Group, Inc. ("IMG")). Armada’s products are offered in the United States while IMG and the insurance and reinsurance business write accident and health products on a worldwide basis:

Accident and Health insurance and reinsurance—Sirius Group is an insurer of accident and health business in the United States and internationally, on either an admitted or surplus lines basis, as well as a reinsurer of medical expense, travel and personal accident on a treaty or facultative basis worldwide. The MGU unit writes health insurance business worldwide through IMG and within the United States via Armada.

U.S. Specialty

U.S. Specialty consists of Sirius Group's specialty insurance product offerings, which currently includes Environmental, Surety, and Workers’ Compensation.

Environmental underwrites a pure environmental insurance book in the United States consisting of four core products that revolve around pollution coverage, which are premises pollution liability, contractor's pollution liability, contractor's pollution and professional liability.

Surety underwrote commercial surety bonds, including non-construction contract bonds, in a broad range of business segments in the United States. In April 2020, the Company decided to exit the Surety business due to competitive market conditions in that business line and recent economic downturn which presented new risks and challenges for this line of business.

Workers' Compensation is a state-mandated insurance program that provides medical, disability, survivor, burial, and rehabilitation benefits to employees who are injured or killed due to a work-related injury or illness.

Runoff & Other

Runoff & Other includes the results of Sirius Global Solutions Holding Company ("Sirius Global Solutions"), which specializes in the acquisition and management of runoff liabilities for insurance and reinsurance companies, both in the United States and internationally, as well as asbestos risks, environmental risks and other long-tailed liability exposures.

The following tables summarize the segment results for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	248.2		$	88.8		$	22.6		$	(3.6)	$	—	$	356.0
Net written premiums	$	192.2		$	72.2		$	20.5		$	(2.6)	$	—	$	282.3
Net earned insurance and reinsurance premiums	$	243.5		$	114.3		$	17.2		$	(2.4)	$	—	$	372.6
Loss and allocated LAE(1)	(194.5)			(84.6)			(11.1)			(1.1)		—		(291.3)
Insurance and reinsurance acquisition expenses	(51.8)			(36.6)			(4.0)			(0.8)		9.6		(83.6)
Technical (loss) profit	(2.8)			(6.9)			2.1			(4.3)		9.6		(2.3)
Unallocated LAE(2)	(7.7)			(0.5)			(0.2)			(1.0)		(4.7)		(14.1)
Other underwriting expenses	(25.3)			(5.7)			(4.3)			(1.3)		(4.7)		(41.3)
Underwriting (loss) income	(35.8)			(13.1)			(2.4)			(6.6)		0.2		(57.7)
Service fee revenue(3)	—			26.3			—			0.9		(10.7)		16.5
Managing general underwriter unallocated LAE	—			(5.8)			—			—		5.8		—
Managing general underwriter other underwriting expenses	—			(4.7)			—			—		4.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(11.0)			—			(0.9)		—		(11.9)
Underwriting (loss) income, including net service fee income	(35.8)			(8.3)			(2.4)			(6.6)		—		(53.1)
Net investment income														1.7
Net realized investment gains														(3.8)
Net unrealized investment gains														31.2
Net foreign exchange (losses)														(21.3)
Other revenue(5)														(0.7)
General and administrative expenses(6)														(22.5)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(8.1)
Pre-tax (loss)														$	(80.5)
Underwriting Ratios(7)
Loss ratio	83.0		%	74.5		%	65.7		%	NM		NM		82.0		%
Acquisition expense ratio	21.3		%	32.0		%	23.3		%	NM		NM		22.4		%
Other underwriting expense ratio	10.4		%	5.0		%	25.0		%	NM		NM		11.1		%
Combined ratio(7)	114.7		%	111.5		%	114.0		%	NM		NM		115.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	256.3		$	137.4		$	17.9		$	2.1	$	—	$	413.7
Net written premiums	$	202.6		$	104.6		$	14.3		$	0.8	$	—	$	322.3
Net earned insurance and reinsurance premiums	$	249.5		$	115.1		$	9.1		$	0.5	$	—	$	374.2
Loss and allocated LAE(1)	(261.7)			(63.6)			(8.2)			(0.9)		—		(334.4)
Insurance and reinsurance acquisition expenses	(54.3)			(32.5)			(2.0)			(0.1)		13.8		(75.1)
Technical (loss) profit	(66.5)			19.0			(1.1)			(0.5)		13.8		(35.3)
Unallocated LAE(2)	(8.4)			(2.0)			(0.1)			(0.2)		(3.5)		(14.2)
Other underwriting expenses	(20.8)			(6.8)			(2.7)			(1.4)		(3.7)		(35.4)
Underwriting (loss) income	(95.7)			10.2			(3.9)			(2.1)		6.6		(84.9)
Service fee revenue(3)	—			31.0			—			—		(14.6)		16.4
Managing general underwriter unallocated LAE	—			(4.3)			—			—		4.3		—
Managing general underwriter other underwriting expenses	—			(3.7)			—			—		3.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(15.1)			—			(1.2)		—		(16.3)
Underwriting (loss) income, including net service fee income	(95.7)			18.1			(3.9)			(3.3)		—		(84.8)
Net investment income														22.8
Net realized investment gains														15.3
Net unrealized investment gains														53.9
Net foreign exchange gains														4.9
Other revenue(5)														(0.1)
General and administrative expenses(6)														(11.7)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(7.7)
Pre-tax (loss)														$	(11.3)
Underwriting Ratios(7)
Loss ratio	108.3		%	57.0		%	91.2		%	NM		NM		93.2		%
Acquisition expense ratio	21.8		%	28.2		%	22.0		%	NM		NM		20.1		%
Other underwriting expense ratio	8.3		%	5.9		%	29.7		%	NM		NM		9.5		%
Combined ratio(7)	138.4		%	91.1		%	142.9		%	NM		NM		122.8		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

The following tables summarize the segment results for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	927.0		$	434.6		$	68.9		$	65.7	$	—	$	1,496.2
Net written premiums	$	758.1		$	334.9		$	59.5		$	65.7	$	—	$	1,218.2
Net earned insurance and reinsurance premiums	$	719.4		$	345.4		$	45.2		$	67.1	$	—	$	1,177.1
Loss and allocated LAE(1)	(600.2)			(234.5)			(29.2)			(61.2)		—		(925.1)
Insurance and reinsurance acquisition expenses	(156.4)			(98.9)			(10.4)			(0.9)		30.2		(236.4)
Technical (loss) profit	(37.2)			12.0			5.6			5.0		30.2		15.6
Unallocated LAE(2)	(17.9)			(2.8)			(0.4)			(11.8)		(14.8)		(47.7)
Other underwriting expenses	(67.1)			(18.0)			(12.4)			(3.7)		(14.4)		(115.6)
Underwriting (loss) income	(122.2)			(8.8)			(7.2)			(10.5)		1.0		(147.7)
Service fee revenue(3)	—			85.3			—			0.9		(33.4)		52.8
Managing general underwriter unallocated LAE	—			(18.0)			—			—		18.0		—
Managing general underwriter other underwriting expenses	—			(14.4)			—			—		14.4		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(36.2)			—			(3.8)		—		(40.0)
Underwriting (loss) income, including net service fee income	(122.2)			7.9			(7.2)			(13.4)		—		(134.9)
Net investment income														30.0
Net realized investment gains														23.6
Net unrealized investment (losses)														(3.9)
Net foreign exchange (losses)														(18.9)
Other revenue(5)														(22.5)
General and administrative expenses(6)														(50.4)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.8)
Pre-tax (loss)														$	(212.6)
Underwriting Ratios(7)
Loss ratio	85.9		%	68.7		%	65.5		%	NM		NM		82.6		%
Acquisition expense ratio	21.7		%	28.6		%	23.0		%	NM		NM		20.1		%
Other underwriting expense ratio	9.3		%	5.2		%	27.4		%	NM		NM		9.8		%
Combined ratio(7)	116.9		%	102.5		%	115.9		%	NM		NM		112.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	1,008.4		$	459.5		$	50.5		$	4.7	$	—	$	1,523.1
Net written premiums	$	805.2		$	360.1		$	42.0		$	1.5	$	—	$	1,208.8
Net earned insurance and reinsurance premiums	$	705.7		$	330.0		$	19.9		$	1.2	$	—	$	1,056.8
Loss and allocated LAE(1)	(558.0)			(198.6)			(14.7)			(4.4)		—		(775.7)
Insurance and reinsurance acquisition expenses	(149.9)			(95.1)			(4.5)			(2.6)		36.7		(215.4)
Technical (loss) profit	(2.2)			36.3			0.7			(5.8)		36.7		65.7
Unallocated LAE(2)	(17.1)			(5.5)			(0.2)			(0.9)		(11.1)		(34.8)
Other underwriting expenses	(64.0)			(18.8)			(7.6)			(4.6)		(11.2)		(106.2)
Underwriting (loss) income	(83.3)			12.0			(7.1)			(11.3)		14.4		(75.3)
Service fee revenue(3)	—			97.6			—			—		(39.3)		58.3
Managing general underwriter unallocated LAE	—			(13.7)			—			—		13.7		—
Managing general underwriter other underwriting expenses	—			(11.2)			—			—		11.2		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(46.3)			—			(3.0)		—		(49.3)
Underwriting (loss) income, including net service fee income	(83.3)			38.4			(7.1)			(14.3)		—		(66.3)
Net investment income														67.3
Net realized investment gains														39.9
Net unrealized investment gains														143.4
Net foreign exchange gains														9.4
Other revenue(5)														(7.0)
General and administrative expenses(6)														(31.3)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.3)
Pre-tax income														$	120.3
Underwriting Ratios(7)
Loss ratio	81.5		%	61.8		%	74.9		%	NM		NM		76.7		%
Acquisition expense ratio	21.2		%	28.8		%	22.6		%	NM		NM		20.4		%
Other underwriting expense ratio	9.1		%	5.7		%	38.2		%	NM		NM		10.0		%
Combined ratio(7)	111.8		%	96.3		%	135.7		%	NM		NM		107.1		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	86.7	$	57.3	$	20.5	$	0.8	$	165.3
Europe	49.3		7.0		—		—		56.3
Canada, the Caribbean, Bermuda and Latin America	25.9		2.3		—		(3.6)		24.6
Asia and Other	30.3		5.6		—		0.2		36.1
Total net written premiums by client location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3
Total net written premiums by underwriting location:
United States	$	53.8	$	28.6	$	20.5	$	0.8	$	103.7
Europe	84.9		43.4		—		—		128.3
Canada, the Caribbean, Bermuda and Latin America	42.8		0.2		—		(3.6)		39.4
Asia and Other	10.7		—		—		0.2		10.9
Total net written premiums by underwriting location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	112.8	$	87.6	$	14.3	$	0.7	$	215.4
Europe	29.7		5.8		—		(0.1)		35.4
Canada, the Caribbean, Bermuda and Latin America	24.5		3.7		—		0.1		28.3
Asia and Other	35.6		7.5		—		0.1		43.2
Total net written premiums by client location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3
Total net written premiums by underwriting location:
United States	$	20.2	$	36.9	$	—	$	0.7	$	57.8
Europe	81.9		68.1		14.3		—		164.3
Canada, the Caribbean, Bermuda and Latin America	91.3		(0.6)		—		—		90.7
Asia and Other	9.2		0.2		—		0.1		9.5
Total net written premiums by underwriting location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	297.9	$	288.7	$	59.5	$	68.4	$	714.5
Europe	264.8		19.4		—		0.4		284.6
Canada, the Caribbean, Bermuda and Latin America	74.2		10.1		—		(3.6)		80.7
Asia and Other	121.2		16.7		—		0.5		138.4
Total net written premiums by client location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2
Total net written premiums by underwriting location:
United States	$	162.5	$	185.7	$	59.5	$	68.4	$	476.1
Europe	376.3		149.4		—		0.4		526.1
Canada, the Caribbean, Bermuda and Latin America	174.6		(0.3)		—		(3.6)		170.7
Asia and Other	44.7		0.1		—		0.5		45.3
Total net written premiums by underwriting location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	382.1	$	301.2	$	42.0	$	1.0	$	726.3
Europe	207.7		18.9		—		0.1		226.7
Canada, the Caribbean, Bermuda and Latin America	70.2		10.7		—		0.1		81.0
Asia and Other	145.2		29.3		—		0.3		174.8
Total net written premiums by client location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8
Total net written premiums by underwriting location:
United States	$	57.8	$	136.0	$	—	$	1.0	$	194.8
Europe	368.0		190.1		42.0		0.2		600.3
Canada, the Caribbean, Bermuda and Latin America	334.4		33.4		—		—		367.8
Asia and Other	45.0		0.6		—		0.3		45.9
Total net written premiums by underwriting location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8

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Reserves for unpaid losses and loss adjustment expenses

9 Months Ended

Sep. 30, 2020

Insurance [Abstract]

Reserves for unpaid losses and loss adjustment expenses

Reserves for unpaid losses and loss adjustment expenses

The following table summarizes the loss and LAE reserve activities of Sirius Group for the three and nine months ended September 30, 2020 and 2019:

	Three months ended September 30,				Nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross beginning balance	$	2,515.1	$	2,023.3	$	2,331.5	$	2,016.7
Less beginning reinsurance recoverable on unpaid losses	(442.2)		(357.4)		(410.3)		(350.2)
Net loss and LAE reserve balance	2,072.9		1,665.9		1,921.2		1,666.5
Losses and LAE incurred relating to:
Current year losses	305.5		342.2		967.5		723.6
Prior years losses	(0.1)		6.4		5.3		86.9
Total net incurred losses and LAE	305.4		348.6		972.8		810.5
Foreign currency translation adjustment to net loss and LAE reserves	20.8		(15.3)		12.2		(15.3)
Accretion of fair value adjustment to net loss and LAE reserves	0.1		—		0.1		0.1
Loss and LAE paid relating to:
Current year losses	81.6		97.7		149.2		254.8
Prior years losses	127.2		108.0		566.7		413.5
Total loss and LAE payments	208.8		205.7		715.9		668.3
Net ending balance	2,190.4		1,793.5		2,190.4		1,793.5
Plus ending reinsurance recoverable on unpaid losses	482.5		392.9		482.5		392.9
Gross ending balance	$	2,672.9	$	2,186.4	$	2,672.9	$	2,186.4

Loss and LAE development - Three Months Ended September 30, 2020

For the three months ended September 30, 2020, Sirius Group had a net favorable loss reserve development of $0.1 million. Favorable loss reserve development in U.S. Specialty ($0.8 million) and Runoff & Other ($0.4 million) were partially offset by unfavorable loss reserve development in Global Reinsurance ($1.3 million).

Loss and LAE development - Three Months Ended September 30, 2019

For the three months ended September 30, 2019, Sirius Group had net unfavorable loss reserve development of $6.4 million. Increases in loss reserve estimates were recorded in Global Reinsurance ($10.9 million) due to higher than expected activity in the Casualty Reinsurance book. These increases were partially offset by favorable loss reserve development in Global A&H ($5.8 million).

Loss and LAE development - Nine Months Ended September 30, 2020

For the nine months ended September 30, 2020, Sirius Group had net unfavorable loss reserve development of $5.3 million. Increases in loss reserve estimates for Global Reinsurance ($14.9 million) were partially offset by favorable loss reserve development in Global A&H ($7.6 million) and U.S. Specialty ($2.0 million). Within Global Reinsurance, unfavorable loss reserve development in Other Property ($21.6 million), Aviation & Space ($10.1 million) and Casualty Reinsurance ($9.2 million) was partially offset by favorable loss reserve development in Property Catastrophe Excess Reinsurance ($22.5 million). The reduction in Property Catastrophe Excess Reinsurance was due to reductions in reserve estimates for prior year catastrophe events, mainly Typhoons Faxai and Hagibis.

Loss and LAE development - Nine Months Ended September 30, 2019 For the nine months ended September 30, 2019, Sirius Group had net unfavorable loss reserve development of $86.9 million. Increases in loss reserve estimates were recorded in Global Reinsurance ($82.7 million) and Runoff & Other ($5.4 million). The unfavorable loss reserve development in Global Reinsurance was primarily attributable to higher prior year catastrophe events, including Typhoon Jebi and Hurricanes Michael, Florence, and Irma.

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Third party reinsurance

9 Months Ended

Sep. 30, 2020

Insurance [Abstract]

Third party reinsurance

Third party reinsurance

In the normal course of business, Sirius Group seeks to protect its businesses from losses due to concentration of risk and losses arising from catastrophic events by reinsuring with third-party reinsurers. Sirius Group remains liable for risks reinsured in the event that the reinsurer does not honor its obligations under reinsurance contracts.

At September 30, 2020, Sirius Group had Reinsurance recoverable on paid losses of $70.4 million and Reinsurance recoverable on unpaid losses of $482.5 million. At December 31, 2019, Sirius Group had Reinsurance recoverable on paid losses of $73.9 million and Reinsurance recoverable on unpaid losses of $410.3 million. Because retrocessional reinsurance contracts do not relieve Sirius Group of its obligation to its insureds, the collectability of balances due from Sirius Group's reinsurers is important to its financial strength. Sirius Group monitors the financial strength and ratings of retrocessionaires on an ongoing basis. Uncollectible amounts historically have not been significant. (See Note 7.)

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Allowance for expected credit losses

9 Months Ended

Sep. 30, 2020

Credit Loss [Abstract]

Allowance for expected credit losses

Allowance for expected credit losses

Sirius Group is exposed to credit losses primarily through sales of its insurance and reinsurance products and services. The financial assets in scope of the current expected credit losses impairment model primarily include Sirius Group's premium receivables and reinsurance recoverables. Sirius Group pools the premium receivables and reinsurance recoverables by counterparty credit rating and applies a credit default rate that is determined based on the studies published by the rating agencies (e.g., A.M. Best, Standard & Poor's ("S&P")). In circumstances where ratings are unavailable, Sirius Group applies an internally developed default rate based on historical experience, reference data including research publications, and other relevant inputs.

To estimate the allowance for expected credit losses, Sirius Group considered the current and expected future economic and market conditions surrounding the COVID-19 pandemic. To the extent the current environment continues beyond our expectations or deteriorates further, we may experience further increases to our allowance for credit losses related to COVID-19.

As of September 30, 2020, Sirius Group's allowance for expected credit losses is as follows:

(in millions)	Gross Assets in Scope		Allowance for Expected Credit Losses
Premiums receivable & Funds held by ceding companies	$	1,033.1	$	10.6
Reinsurance recoverable on unpaid and paid loss	552.9		3.9
MGU Trade receivables(1)	17.2		0.4
Total as of September 30, 2020	$	1,603.2	$	14.9

(1) Included as part of Other assets on the Consolidated Balance Sheet

Sirius Group recorded no changes to the allowance for expected credit losses during three and nine months ended September 30, 2020.

Sirius Group monitors counterparty credit ratings and macroeconomic conditions, and considers the most current A.M. Best and S&P credit ratings to determine the allowance each quarter. Of the total gross assets in scope as of September 30, 2020, approximately 67% were balances with counterparties rated by either A.M. Best or S&P. Of the total rated, 63% were rated A- or better.

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Investment securities

9 Months Ended

Sep. 30, 2020

Investments, Debt and Equity Securities [Abstract]

Investment securities

Investment securities

Sirius Group's invested assets consist of investment securities and other long-term investments held for general investment purposes. The portfolio of investment securities includes fixed maturity investments, short-term investments, equity securities, and other-long term investments which are all classified as trading securities. Realized and unrealized investment gains and losses on trading securities are reported in pre-tax revenues.

Net Investment Income

Sirius Group's net investment income is comprised primarily of interest income along with associated amortization of premium and accretion of discount on Sirius Group's fixed maturity investments, dividend income from its equity investments, and interest income from its short-term investments.

Net investment income for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	10.1	$	12.8	$	31.5	$	40.0
Short-term investments	0.6		4.1		5.2		12.0
Equity securities	0.8		2.7		5.5		12.5
Other long-term investments(1)(2)	(6.0)		5.2		(2.7)		12.3
Total investment income	5.5		24.8		39.5		76.8
Investment expenses	(3.8)		(2.0)		(9.5)		(9.5)
Net investment income	$	1.7	$	22.8	$	30.0	$	67.3

(1)Includes $(8.1) and $0.0 of interest on funds held for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $(7.5) and $0.6 of interest on funds held for the nine months ended September 30, 2020 and 2019, respectively.

Net Realized and Unrealized Investment Gains (Losses)

Net realized and unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross realized gains	$	41.3	$	22.1	$	140.7	$	63.1
Gross realized (losses)	(45.1)		(6.8)		(117.1)		(23.2)
Net realized (losses) gains on investments(1)(2)	(3.8)		15.3		23.6		39.9
Net unrealized gains (losses) on investments(3)(4)	31.2		53.9		(3.9)		143.4
Net realized and unrealized gains (losses) on investments	$	27.4	$	69.2	$	19.7	$	183.3

(1)Includes $(11.2) and $14.0 of realized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $5.4 and $34.5 of realized gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

(3)Includes $(16.7) and $33.9 of unrealized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(4)Includes $(29.8) and $51.7 of unrealized (losses) gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

Net realized investment gains

Net realized investment gains for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(0.4)	$	7.5	$	17.3	$	22.4
Equity securities	1.0		1.7		(5.0)		(0.1)
Short-term investments	(6.2)		6.5		(2.4)		9.7
Derivative instruments	1.8		(0.7)		10.3		(1.5)
Other long-term investments	—		0.3		3.4		9.4
Net realized investment (losses) gains	$	(3.8)	$	15.3	$	23.6	$	39.9

Net unrealized investment gains (losses)

Net unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(1.0)	$	31.4	$	2.2	$	72.1
Equity securities	18.5		12.0		(33.7)		50.4
Short-term investments	(3.1)		4.6		(3.2)		6.4
Derivative instruments	(0.8)		0.9		1.4		0.2
Other long-term investments	17.6		5.0		29.4		14.3
Net unrealized investment gains (losses)	$	31.2	$	53.9	$	(3.9)	$	143.4

The following table summarizes the amount of total gains (losses) included in earnings attributable to unrealized investment gains (losses) for Level 3 investments for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	—	$	—	$	0.3	$	—
Other long-term investments	8.2		(0.3)		3.1		10.1
Total unrealized investment gains (losses) – Level 3 investments	$	8.2	$	(0.3)	$	3.4	$	10.1

Investment Holdings

Fixed maturity investments

The cost or amortized cost, gross unrealized investment gains (losses), net foreign currency gains (losses), and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	471.4	$	10.0	$	(0.8)	$	1.3	$	481.9
Asset-backed securities	740.0		8.4		(12.4)		(4.4)		731.6
Residential mortgage-backed securities	393.8		22.2		(0.9)		1.4		416.5
U.S. government and government agency	119.2		0.8		—		(3.6)		116.4
Commercial mortgage-backed securities	120.8		3.1		(1.7)		—		122.2
Non-U.S. government and government agency	71.4		0.4		(0.1)		(0.6)		71.1
Preferred stocks	14.9		3.1		(0.1)		—		17.9
U.S. States, municipalities and political subdivision	1.2		0.1		—		—		1.3
Total fixed maturity investments	$	1,932.7	$	48.1	$	(16.0)	$	(5.9)	$	1,958.9

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	458.6	$	5.2	$	(1.2)	$	11.5	$	474.1
Asset-backed securities	489.4		1.4		(3.9)		(0.1)		486.8
Residential mortgage-backed securities	426.2		10.5		(1.4)		3.6		438.9
U.S. government and government agency	111.5		0.7		(0.4)		(1.3)		110.5
Commercial mortgage-backed securities	88.5		0.9		(0.6)		0.2		89.0
Non-U.S. government and government agency	63.7		—		(0.7)		—		63.0
Preferred stocks	17.0		—		—		—		17.0
U.S. States, municipalities and political subdivision	1.7		—		—		—		1.7
Total fixed maturity investments	$	1,656.6	$	18.7	$	(8.2)	$	13.9	$	1,681.0

The weighted average duration of Sirius Group's fixed income portfolio as of September 30, 2020 was approximately 1.1 years, including short-term investments, and approximately 1.6 years excluding short-term investments.

The cost or amortized cost and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019 are presented below by contractual maturity. Actual maturities could differ from contractual maturities because borrowers may have the right to call or prepay certain obligations with or without call or prepayment penalties.

	September 30, 2020				December 31, 2019
(Millions)	Cost or amortized cost		Fair value		Cost or amortized cost		Fair value
Due in one year or less	$	203.2	$	212.2	$	85.0	$	88.4
Due after one year through five years	406.7		404.4		479.1		490.3
Due after five years through ten years	41.0		41.7		46.3		46.0
Due after ten years	12.3		12.4		25.1		24.6
Mortgage-backed and asset-backed securities	1,254.6		1,270.3		1,004.1		1,014.7
Preferred stocks	14.9		17.9		17.0		17.0
Total	$	1,932.7	$	1,958.9	$	1,656.6	$	1,681.0

The following table summarizes the ratings and fair value of fixed maturity investments held in Sirius Group's investment portfolio as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
AAA	$	807.8	$	559.8
AA	734.4		724.3
A	213.7		219.0
BBB	99.2		95.8
Other	103.8		82.1
Total fixed maturity investments(1)	$	1,958.9	$	1,681.0

(1)Credit ratings are assigned based on the following hierarchy: 1) Standard & Poor's ("S&P") and 2) Moody's Investors Service ("Moody's").

At September 30, 2020, the above totals included $43.8 million of sub-prime securities. Of this total, $21.5 million was rated AAA, $18.7 million rated AA, $3.5 million rated A and $0.1 million classified as Other. At December 31, 2019, the above totals included $43.3 million of sub-prime securities. Of this total, $21.7 million was rated AAA, $18.4 million rated AA, $3.1 million rated A and $0.1 million classified as Other.

Equity securities and Other long-term investments

The cost or amortized cost, gross unrealized investment gains and losses, net foreign currency gains, and fair values of Sirius Group's equity securities and other long-term investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	170.0	$	27.8	$	(39.7)	$	0.6	$	158.7
Other long-term investments	$	327.5	$	75.5	$	(24.4)	$	9.4	$	388.0

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	379.2	$	55.6	$	(37.3)	$	7.7	$	405.2
Other long-term investments	$	315.4	$	49.9	$	(29.3)	$	10.8	$	346.8

Equity securities at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Fixed income mutual funds	$	1.8	$	175.3
Common stocks	170.1		228.1
Other equity securities(1)	(13.2)		1.8
Total Equity securities	$	158.7	$	405.2

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

Other long-term investments at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Hedge funds and private equity funds	$	301.1	$	269.0
Limited liability companies and private equity securities	86.9		77.8
Total other long-term investments	$	388.0	$	346.8

Hedge Funds and Private Equity Funds

Sirius Group holds investments in hedge funds and private equity funds, which are included in Other long-term investments. The fair value of these investments has been estimated using the net asset value of the funds. As of September 30, 2020, Sirius Group held investments in 10 hedge funds and 32 private equity funds. The largest investment in a single fund was $66.3 million as of September 30, 2020 and $51.6 million as of December 31, 2019.

The following table summarizes investments in hedge funds and private equity interests by investment objective and sector as of September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair value		Unfunded commitments		Fair value		Unfunded commitments
Hedge funds:
Long/short multi-sector	$	54.9	$	—	$	53.0	—
Distressed mortgage credit	66.3		—		51.6		—
Private credit	22.1		—		21.5		—
Multi-sector	5.8		—		—		—
Other	1.2		—		1.4		—
Total hedge funds	150.3		—		127.5		—
Private equity funds:
Energy infrastructure & services	56.6		30.7		53.6		34.6
Multi-sector	13.4		8.1		8.7		7.8
Healthcare	29.1		6.3		25.9		10.4
Life settlement	20.6		—		23.9		—
Manufacturing/Industrial	27.7		—		27.6		3.9
Private equity secondaries	0.6		0.8		0.6		0.8
Other	2.8		1.8		1.2		2.6
Total private equity funds	150.8		47.7		141.5		60.1
Total hedge and private equity funds included in Other long-term investments	$	301.1	$	47.7	$	269.0	$	60.1

Redemption of investments in certain hedge funds is subject to restrictions including lock-up periods where no redemptions or withdrawals are allowed, restrictions on redemption frequency, and advance notice periods for redemptions. Amounts requested for redemptions remain subject to market fluctuations until the redemption effective date, which generally falls at the end of the defined redemption period.

The following summarizes the September 30, 2020 fair value of hedge funds subject to restrictions on redemption frequency and advance notice period requirements for investments in active hedge funds:

	Notice Period
Redemption Frequency (Millions)	1-29 days notice		30-59 days notice		60-89 days notice		90-119 days notice		120+ days notice		Total
Monthly	$	5.8	$	—	$	30.5	$	—	$	—	$	36.3
Quarterly	—		0.6		24.4		66.3		—		$	91.3
Semi-annual	—		—		0.3		—		—		$	0.3
Annual	—		—		—		0.3		22.1		$	22.4
Total	$	5.8	$	0.6	$	55.2	$	66.6	$	22.1	$	150.3

Certain of the hedge fund and private equity fund investments in which Sirius Group is invested are no longer active and are in the process of disposing of their underlying investments. Distributions from such funds are remitted to investors as the fund's underlying investments are liquidated. As of September 30, 2020, no distributions were outstanding from these investments.

Investments in private equity funds are generally subject to a "lock-up" period during which investors may not request a redemption. Distributions prior to the expected termination date of the fund may be limited to dividends or proceeds arising from the liquidation of the fund's underlying investments. In addition, certain private equity funds provide an option to extend the lock-up period at either the sole discretion of the fund manager or upon agreement between the fund and the investors.

As of September 30, 2020, investments in private equity funds were subject to lock-up periods as follows:

(Millions)	1 - 3 years		3 – 5 years		5 – 10 years		Total
Private Equity Funds – expected lock up period remaining	$	53.9	$	19.0	$	77.9	$	150.8

Investments Held on Deposit or as Collateral

As of September 30, 2020 and December 31, 2019 investments of $1,202.9 million and $1,309.5 million, respectively, were held in trusts required to be maintained in relation to various reinsurance agreements. Sirius Group's reinsurance operations are required to maintain deposits with certain insurance regulatory agencies in order to maintain their insurance licenses. The fair value of such deposits that are included within total investments totaled $1,217.9 million and $1,315.5 million as of September 30, 2020 and December 31, 2019, respectively.

As of September 30, 2020, Sirius Group held $0.1 million of collateral in the form of short-term investments associated with Interest Rate Cap agreements. (See Note 12.)

Unsettled investment purchases and sales

As of September 30, 2020 and December 31, 2019 Sirius Group reported $29.9 million and $2.3 million, respectively, in Accounts payable on unsettled investment purchases.

As of September 30, 2020 and December 31, 2019, Sirius Group reported $19.2 million and $6.7 million, respectively, in Accounts receivable on unsettled investment sales.

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Fair value measurements

9 Months Ended

Sep. 30, 2020

Fair Value Disclosures [Abstract]

Fair value measurements

Fair value measurements

Fair value measurements are categorized into a hierarchy that distinguishes between inputs based on market data from independent sources ("observable inputs") and a reporting entity's internal assumptions based upon the best information available when external market data is limited or unavailable ("unobservable inputs"). Quoted prices in active markets for identical assets or liabilities have the highest priority ("Level 1"), followed by observable inputs other than quoted prices, including prices for similar but not identical assets or liabilities ("Level 2"), and unobservable inputs, including the reporting entity's estimates of the assumptions that market participants would use, having the lowest priority ("Level 3").

The availability of observable inputs can vary from financial instrument to financial instrument and is affected by a wide variety factors including, for example, the type of financial instrument, whether the financial instrument is new and not yet established in the marketplace, and other characteristics particular to the instrument. To the extent that valuation is based on models or inputs that are less observable or unobservable in the market, the determination of fair value requires significantly more judgment.

Accordingly, the degree of judgment exercised by management in determining fair value is greatest for instruments categorized in Level 3. In periods of market dislocation, the observability of prices and inputs may be reduced for many instruments. This may lead the Company to change the selection of the valuation technique (for example, from market to cash flow approach) or to use multiple valuation techniques to estimate the fair value of a financial instrument. These circumstances could cause an instrument to be reclassified between levels within the fair value hierarchy. Investments valued using Level 1 inputs include fixed maturity investments, primarily investments in U.S. Treasuries Bills and Notes, equity securities, and short-term investments. Investments valued using Level 2 inputs are primarily comprised of fixed maturity investments, which have been disaggregated into classes, including U.S. government and government agency, corporate debt securities, mortgage-backed and asset-backed securities, non-U.S. government and government agency, U.S. state and municipalities and political subdivision and preferred stocks. Investments valued using Level 2 inputs also include certain exchange-traded funds that track U.S. stock indices such as the S&P 500 but are traded on foreign exchanges. Fair value estimates for investments that trade infrequently and have few or no observable market prices are classified as Level 3 measurements. Sirius Group determines when transfers between levels have occurred as of the beginning of the period.

Valuation techniques

Sirius Group uses outside pricing services to assist in determining fair values for its investments. For investments in active markets, Sirius Group uses the quoted market prices provided by outside pricing services to determine fair value. The outside pricing services Sirius Group uses have indicated that they will only provide prices where observable inputs are available. In circumstances where quoted market prices are unavailable or are not considered reasonable, Sirius Group estimates the fair value using industry standard pricing models and observable inputs such as benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers, prepayment speeds, reference data including research publications, and other relevant inputs. Given that many fixed maturity investments do not trade on a daily basis, the outside pricing services evaluate a wide range of fixed maturity investments by regularly drawing parallels from recent trades and quotes of comparable securities with similar features. The characteristics used to identify comparable fixed maturity investments vary by asset type and take into account market convention.

The valuation process above is generally applicable to all of Sirius Group's fixed maturity investments. The techniques and inputs specific to asset classes within Sirius Group's fixed maturity investments for Level 2 securities that use observable inputs are as follows:

U.S. government and government agency

U.S. government and government agency securities consist primarily of debt securities issued by the U.S. Treasury and mortgage pass-through agencies such as the Federal National Mortgage Association, the Federal Home Loan Mortgage Corporation and the Government National Mortgage Association. Fixed maturity investments included in U.S. government and government agency securities are primarily priced by pricing services. When evaluating these securities, the pricing services gather information from market sources and integrate other observations from markets and sector news. Evaluations are updated by obtaining broker-dealer quotes and other market information including actual trade volumes, when available. The fair value of each security is individually computed using analytical models that incorporate option-adjusted spreads and other daily interest rate data.

Non-U.S. government and government agency

Non-U.S. government and government agency securities consist of debt securities issued by non-U.S. governments and their agencies along with supranational organizations (also known as sovereign debt securities). Securities held in these sectors are primarily priced by pricing services that employ proprietary discounted cash flow models to value the securities. Key quantitative inputs for these models are daily observed benchmark curves for treasury, swap, and high issuance credits. The pricing services then apply a credit spread for each security, which is developed by in-depth and real-time market analysis. For securities in which trade volume is low, the pricing services utilize data from more frequently traded securities with similar attributes. These models may also be supplemented by daily market and credit research for international markets.

Corporate debt securities

Corporate debt securities consist primarily of investment-grade debt of a wide variety of U.S. and non-U.S. corporate issuers and industries. The corporate fixed maturity investments are primarily priced by pricing services. When evaluating these securities, the pricing services gather information from market sources regarding the issuer of the security and obtain credit data, as well as other observations, from markets and sector news. Evaluations are updated by obtaining broker-dealer quotes and other market information including actual trade volumes, when available. The pricing services also consider the specific terms and conditions of the securities, including any specific features that may influence risk.

Mortgage-backed and asset-backed securities

The fair value of mortgage and asset-backed securities is primarily priced by pricing services using a pricing model that utilizes information from market sources and leveraging similar securities. Key inputs include benchmark yields, reported trades, underlying tranche cash flow data and collateral performance, plus new issue data, as well as broker-dealer quotes, issuer spreads, two-sided markets, benchmark securities, bids, offers, and reference data including issuer, vintage, loan type, collateral attributes, prepayment speeds, default rates, recovery rates, cash flow stress testing, credit quality ratings, and market research publications.

U.S. states, municipalities and political subdivisions

The U.S. states, municipalities and political subdivisions portfolio contains debt securities issued by U.S. domiciled state and municipal entities. These securities are generally priced by independent pricing services using the techniques described for U.S. government and government agency securities described above.

Preferred stocks

The fair value of preferred stocks is generally priced by independent pricing services using an evaluated pricing model that calculates the appropriate spread over a comparable security for each issue. Key inputs include exchange prices (underlying and common stock of the same issuer), benchmark yields, reported trades, broker-dealer quotes, issuer spreads, two-sided markets, benchmark securities, bids, offers, and reference data including sector, coupon, credit quality ratings, duration, credit enhancements, early redemption features, and market research publications.

Level 3 Investments

Level 3 valuations are generated from techniques that use assumptions not observable in the market. These unobservable assumptions reflect Sirius Group's assumptions about what market participants would use in valuing the investment. Generally, certain securities may start out as Level 3 when they are originally issued but, as observable inputs become available in the market, they may be reclassified to Level 2.

Sirius Group employs a number of procedures to assess the reasonableness of the fair value measurements for its other long-term investments, including obtaining and reviewing the audited annual financial statements of hedge funds and private equity funds and periodically discussing each fund's pricing with the fund manager. However, since the fund managers do not provide sufficient information to evaluate the pricing inputs and methods for each underlying investment, the inputs are considered to be unobservable.

The fair values of Sirius Group's investments in private equity securities and private debt instruments have been classified as Level 3 measurements. They are carried at fair value and are initially valued based on transaction price. Their valuation is subsequently estimated based on available evidence such as a market transaction in similar instruments and other financial information for the issuer.

Investments measured using Net Asset Value

The fair value of Sirius Group's investments in hedge funds and private equity funds has been determined using net asset value ("NAV"). The hedge fund's administrator provides quarterly updates of fair value in the form of Sirius Group's proportional interest in the underlying fund's NAV, which is deemed to approximate fair value, generally with a three month delay in valuation. The fair value of investment in hedge funds is measured using the NAV practical expedient and therefore has been not categorized within the fair value hierarchy. The private equity funds provide quarterly or semi-annual partnership capital statements with a three or six month delay which are used as a basis for valuation. These private equity investments vary in investment strategies and are not actively traded in any open markets. Due to a lag in reporting, some of the fund managers, fund administrators, or both, are unable to provide final fund valuations as of the Company's reporting date. In these circumstances, Sirius Group estimates the return of the current period and uses all credible information available. This includes utilizing preliminary estimates reported by its fund managers and using other information that is available to Sirius Group with respect to the underlying investments, as necessary.

Fair Value Measurements by Level

The following tables summarize Sirius Group's financial assets and liabilities measured at fair value as of September 30, 2020 and December 31, 2019 by level:

	September 30, 2020
(Millions)	Fair Value		Level 1 Inputs		Level 2 Inputs		Level 3 Inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	116.4	$	115.4	$	1.0	$	—
Corporate debt securities	481.9		—		481.9		—
Residential mortgage-backed securities	416.5		—		416.5		—
Asset-backed securities	731.6		—		731.6		—
Commercial mortgage-backed securities	122.2		—		122.2		—
Non-U.S. government and government agency	71.1		20.8		50.3		—
Preferred stocks	17.9		—		15.3		2.6
U.S. States, municipalities, and political subdivision	1.3		—		1.3		—
Total fixed maturity investments	1,958.9		136.2		1,820.1		2.6
Equity securities:
Fixed income mutual funds	1.8		1.8		—		—
Common stocks	170.1		170.1		—		—
Other equity securities(1)	(13.2)		(16.9)		3.7		—
Total equity securities	158.7		155.0		3.7		—
Short-term investments	1,132.6		1,068.4		64.2		—
Other long-term investments(2)	86.9		—		—		86.9
Total investments	$	3,337.1	$	1,359.6	$	1,888.0	$	89.5
Loan participation	28.5		—		—		28.5
Derivative instruments	7.7		6.6		—		1.1
Total assets measured at fair value	$	3,373.3	$	1,366.2	$	1,888.0	$	119.1
Liabilities measured at fair value
Contingent consideration liabilities	$	0.3	$	—	$	—	$	0.3
Derivative instruments	3.6		0.1		—		3.5
Total liabilities measured at fair value	$	3.9	$	0.1	$	—	$	3.8

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

(2)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

	December 31, 2019
(Millions)	Fair value		Level 1 inputs		Level 2 inputs		Level 3 inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	110.5	$	109.1	$	1.4	$	—
Corporate debt securities	474.1		—		474.1		—
Asset-backed securities	486.8		—		486.8		—
Residential mortgage-backed securities	438.9		—		438.9		—
Commercial mortgage-backed securities	89.0		—		89.0		—
Non-U.S. government and government agency	63.0		31.7		31.3		—
Preferred stocks	17.0		—		—		17.0
U.S. States, municipalities, and political subdivision	1.7		—		1.7		—
Total fixed maturity investments	1,681.0		140.8		1,523.2		17.0
Equity securities:
Fixed income mutual funds	175.3		175.3		—		—
Common stocks	228.1		228.1		—		—
Other equity securities	1.8		—		1.8		—
Total equity securities	405.2		403.4		1.8		—
Short-term investments	1,085.2		1,073.7		11.5		—
Other long-term investments(1)	77.8		—		—		77.8
Total investments	$	3,249.2	$	1,617.9	$	1,536.5	$	94.8
Loan participation	20.0		—		—		20.0
Derivative instruments	11.4		1.3		—		10.1
Total assets measured at fair value	$	3,280.6	$	1,619.2	$	1,536.5	$	124.9
Liabilities measured at fair value
Contingent consideration liabilities	$	28.2	$	—	$	—	$	28.2
Derivative instruments	9.5		0.2		—		9.3
Total liabilities measured at fair value	$	37.7	$	0.2	$	—	$	37.5

(1)Excludes fair value of $269.0 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

Rollforward of Level 3 fair value measurements

The following tables present changes in Level 3 for financial instruments measured at fair value for the three months ended September 30, 2020 and September 30, 2019:

	For the three months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2020	$	2.6	$	78.2	$	27.3	$	1.5	$	(22.9)
Total realized and unrealized gains (losses)	—		8.2		—		(1.7)		(0.3)
Foreign currency gains through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		—		2.5		—		—
Sales/Settlements(2)	—		—		(1.3)		(2.2)		22.9
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $4.5 payment of contingent consideration for the 2017 purchase of Armada.

	For the three months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2019	$	—	$	88.0	$	—	$	(3.6)	$	(30.8)
Total realized and unrealized (losses)	—		(0.3)		—		(2.0)		(2.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.0)		—		—		—
Purchases	17.0		—		—		—		—
Sales/Settlements(2)	—		(6.0)		—		3.4		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

The following tables present changes in Level 3 for financial instruments measured at fair value for the nine months ended September 30, 2020 and September 30, 2019:

	For the nine months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2020	$	17.0	$	77.8	$	20.0	$	0.8	$	(28.2)
Total realized and unrealized gains (losses)	2.6		3.1		—		(20.7)		(0.5)
Foreign currency (losses) through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		5.5		9.9		—		—
Sales/Settlements(2)	(17.0)		—		(1.4)		17.5		28.4
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $10.0 payment of contingent consideration for the 2017 purchase of Armada.

	For the nine months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2019	$	5.4	$	63.6	$	—	$	(0.5)	$	(28.8)
Total realized and unrealized gains (losses)	—		10.6		—		(7.7)		(4.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.5)		—		—		—
Purchases	17.0		15.8		—		—		—
Sales/Settlements(2)	(5.4)		(7.8)		—		6.0		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

Fair value measurements – transfers between levels

There were no transfers between Level 3 and Level 2 measurements during the three and nine months ended September 30, 2020 and 2019, respectively.

Significant Unobservable Inputs

The table below presents information about the significant unobservable inputs used for recurring fair value measurements for certain Level 3 instruments as of September 30, 2020 and December 31, 2019, and includes only those instruments for which information about the inputs is reasonably available to Sirius Group, such as data from independent third-party valuation service providers and from internal valuation models.

(Millions, except share prices)	September 30, 2020
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities (1)	Purchase price of recent transaction	$	32.5	Purchase price	40.63
Preferred stock (1)	Purchase price of recent transaction	$	27.9	Purchase price	7.74
Loan participation (1)	Purchase price of recent transaction	$	18.5	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private equity securities (1)	Multiple of GAAP book value	$	13.3	Book value multiple	Range - 0.73x-0.91x Median - 0.82x
Loan participation (1)	Purchase price of recent transaction	$	10.0	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private debt instrument (1)	Discounted cash flow	$	6.2	Discount yield	Range - 11.87% - 12.32% Median - 12.08%
Private equity securities (1)	Purchase price of recent transaction	$	4.7	Purchase price	7.74
Private convertible debt instrument (1)	Unit price of recent transaction	$	2.0	Purchase price	7.74
Preferred stock (1)	Purchase price of recent transaction	$	1.9	Purchase price	$	1.9
Preferred stock (1)	Purchase price of recent transaction	$	0.7	Purchase price	$	0.7
Equity warrants	Option pricing model	$	0.5	Strike price	$	0.2
Currency swaps (2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Currency forwards(2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Private equity securities (1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Contingent consideration	External valuation model	$	(0.3)	Discounted future payment	$	(0.3)
Weather derivatives (2)	Third party appraisal	$	(3.5)	Broker quote	$	(3.5)

(1)As of September 30, 2020, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

(Millions, except share prices)	December 31, 2019
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities(1)	Share price of recent transaction	$	32.5	Purchase share price	$	40.6
Loan participation(1)	Purchase price of recent transaction	$	20.0	Purchase price	20.0
Preferred stock(1)	Share price of recent transaction	$	17.5	Purchase price	$	7.74
Private equity securities(1)	Multiple of GAAP book value	$	14.2	Book value multiple	0.9
Preferred stock(1)	Purchase price of recent transaction	$	12.2	Purchase price	$	12.2
Private debt instrument(1)	Purchase price of recent transaction	$	7.2	Purchase price	$	9.0
Weather derivatives(2)	Third party appraisal	$	7.0	Broker quote	$	7.0
Private equity securities(1)	Purchase price of recent transaction	$	5.1	Purchase price	$	7.74
Preferred stock(1)	Purchase price of recent transaction	$	4.8	Purchase price	$	4.80
Currency forwards(2)	Third party appraisal	$	2.7	Broker quote	$	2.7
Private equity securities(1)	Purchase price of recent transaction	$	1.0	Purchase price	$	10.0
Equity warrants(2)	Option pricing model	$	0.4	Strike price	$	0.2
Private equity securities(1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Currency swaps(2)	Third party appraisal	$	(3.6)	Broker quote	$	(3.6)
Currency forwards(2)	Third party appraisal	$	(5.7)	Broker quote	$	(5.7)
Contingent consideration	External valuation model	$	(28.2)	Discounted future payments	$	(28.2)

(1)As of December 31, 2019, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

Financial instruments disclosed, but not carried at fair value

Sirius Group uses various financial instruments in the normal course of its business. The carrying values of Cash, Accrued investment income, certain other assets, Accounts payable on unsettled investment purchases, certain other liabilities, and other financial instruments not included in the table below approximated their fair values at September 30, 2020 and December 31, 2019, due to their respective short maturities. As these financial instruments are not actively traded, their respective fair values are classified within Level 3. The following table includes financial instruments for which the carrying value differs from the estimated fair values at September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair Value(1)		Carrying Value		Fair Value(1)		Carrying Value
Liabilities, Mezzanine equity, and Non-controlling interest:
2017 SEK Subordinated Notes	$	298.8	$	301.3	$	294.5	$	291.2
2016 SIG Senior Notes	$	394.7	$	394.5	$	394.5	$	394.0
Series B preference shares	$	244.5	$	197.5	$	186.4	$	223.0

(1)Fair value estimated by internal pricing and considered a Level 3 measurement.

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Debt and standby letters of credit facilities

9 Months Ended

Sep. 30, 2020

Debt Disclosure [Abstract]

Debt and standby letters of credit facilities

Debt and standby letters of credit facilities

Sirius Group's debt outstanding as of September 30, 2020 and December 31, 2019 consisted of the following:

(Millions)	September 30, 2020		Effective Rate(1)		December 31, 2019		Effective Rate(1)
2017 SEK Subordinated Notes, at face value	$	305.0	4.3	%	$	295.0	4.0	%
Unamortized issuance costs	(3.7)				(3.8)
2017 SEK Subordinated Notes, carrying value	301.3				291.2
2016 SIG Senior Notes, at face value	400.0		4.7	%	400.0		4.7	%
Unamortized discount	(2.1)				(2.3)
Unamortized issuance costs	(3.4)				(3.7)
2016 SIG Senior Notes, carrying value	394.5				394.0
Total debt	$	695.8			$	685.2

(1) Effective rate considers the effect of the debt issuance costs.

2017 SEK Subordinated Notes

On September 22, 2017, Sirius Group issued floating rate callable subordinated notes denominated in Swedish kronor ("SEK") in the amount of SEK 2,750.0 million (or $346.1 million on date of issuance) at a 100% issue price ("2017 SEK Subordinated Notes"). The 2017 SEK Subordinated Notes were issued in an offering that was exempt from the registration requirements of the Securities Act of 1933 (the "Securities Act"). The 2017 SEK Subordinated Notes bear interest on their principal amount at a floating rate equal to the applicable Stockholm Interbank Offered Rate ("STIBOR") for the relevant interest period plus an applicable margin, payable quarterly in arrears on March 22, June 22, September 22, and December 22 in each year commencing on December 22, 2017, until maturity in September 2047.

Beginning on September 22, 2022, the 2017 SEK Subordinated Notes may be redeemed, in whole or in part, at Sirius Group's option. In addition, within 90 days following the occurrence of a Specified Event (as defined below), the 2017 SEK Subordinated Notes may be redeemed, in whole but not in part, at Sirius Group's option. "Specified Event" means (a) an "Additional Amounts Event" in connection with a change in laws, rules or regulations as a result of which Sirius Group is obligated to pay additional amounts on the notes in respect of any withholding or deduction for taxes, (b) a "Tax Event" in connection with a change in laws, rules or regulations as a result of which interest on the notes is no longer fully deductible by Sirius Group for income tax purposes in the applicable jurisdiction (to the extent that such interest was so deductible as of the time of such Tax Event), (c) a "Rating Methodology Event" in connection with a change in, or clarification to, the rating methodology of Standard & Poor's or Fitch that results in a materially unfavorable capital treatment of the notes, or (d) a "Regulatory Event" in connection with a change in, or clarification to, applicable supervisory regulations that results in the notes no longer qualifying as Tier 2 Capital.

Sirius Group incurred $4.6 million in expenses related to the issuance of the 2017 SEK Subordinated Notes (including SEK 27.5 million, or $3.5 million, in underwriting fees), which have been deferred and are being recognized into interest expense over the life of the 2017 SEK Subordinated Notes. For the three months ended September 30, 2020 and 2019, Sirius Group recognized $(10.7) million and $15.9 million, respectively, of foreign currency exchange (losses) gains on the remeasurement of the 2017 SEK Subordinated Notes into USD from SEK. For the nine months ended September 30, 2020 and 2019, Sirius Group recognized $(9.9) million and $27.2 million, respectively, of foreign currency exchange (losses) gains on the remeasurement of the 2017 SEK Subordinated Notes into USD from SEK.

Taking into effect the amortization of all underwriting and issuance expenses, and applicable STIBOR, the 2017 SEK Subordinated Notes yielded an effective rate of approximately 4.3% and 4.1% annualized for the three months ended September 30, 2020 and 2019, respectively. The effective rate for the nine months ended September 30, 2020 and 2019 were 4.3% and 4.0% annualized, respectively. Sirius Group recorded $3.3 million and $3.0 million of interest expense, inclusive of amortization of issuance costs on the 2017 SEK Subordinated Notes for the three months ended September 30, 2020 and 2019, respectively. Sirius Group recorded $9.4 million and $8.9 million of interest expense, inclusive of amortization of issuance costs on the 2017 SEK Subordinated Notes for the nine months ended September 30, 2020 and 2019, respectively.

2016 SIG Senior Notes

On November 1, 2016, Sirius Group issued $400.0 million face value of senior unsecured notes ("2016 SIG Senior Notes") at an issue price of 99.209% for net proceeds of $392.4 million after taking into effect both deferrable and non-deferrable issuance costs. The 2016 SIG Senior Notes were issued in an offering that was exempt from the registration requirements of the Securities Act. The 2016 SIG Senior Notes bear an annual interest rate of 4.6%, payable semi-annually in arrears on May 1, and November 1, in each year commencing on May 1, 2017, until maturity in November 2026.

Sirius Group incurred $5.1 million in expenses related to the issuance of the 2016 SIG Senior Notes (including $3.4 million in underwriting fees), which have been deferred and are being recognized into interest expense over the life of the 2016 SIG Senior Notes.

Taking into effect the amortization of the original issue discount and all underwriting and issuance expenses, the 2016 SIG Senior Notes yield an effective rate of approximately 4.7% per annum. Sirius Group recorded $4.8 million, inclusive of amortization of issuance costs on the 2016 SIG Senior Notes, for both three month periods ended September 30, 2020 and 2019. Sirius Group recorded $14.4 million, inclusive of amortization of issuance costs on the 2016 SIG Senior Notes, for both nine month periods ended September 30, 2020 and 2019.

Standby Letter of Credit Facilities

On November 9, 2019, Sirius International Insurance Corporation ("Sirius International"), a wholly owned subsidiary of the Company, renewed two standby letter of credit facility agreements totaling $125 million to provide capital support for Lloyd's Syndicate 1945. The first letter of credit is a renewal of a $90 million facility with Nordea Bank Finland Abp, London Branch, which is issued on an unsecured basis. The second letter of credit is a $35 million facility with DNB Bank ASA, Sweden Branch, $25 million of which is issued on an unsecured basis. Each facility is renewable annually. The above referenced facilities are subject to various affirmative, negative and financial covenants that the Company considers to be customary for such borrowings, including certain minimum net worth and maximum debt to capitalization standards.

Sirius International has other secured letter of credit and trust arrangements with various financial institutions to support its insurance operations. As of September 30, 2020 and December 31, 2019, these secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust of SEK 4.4 billion and SEK 3.4 billion, respectively, or $488.3 million and $363.3 million, respectively (based on the September 30, 2020 and December 31, 2019 SEK to USD exchange rates). As of September 30, 2020 and December 31, 2019, Sirius America Insurance Company's trust arrangements were collateralized by pledged assets and assets in trust of $47.9 million and $57.7 million, respectively. As of September 30, 2020 and December 31, 2019, Sirius Bermuda's letters of credit and trust arrangements were collateralized by pledged assets and assets in trust of $519.9 million and $784.0 million, respectively.

Revolving Credit Facility

In February 2018, Sirius Group, through its indirectly wholly-owned subsidiary Sirius International Group, Ltd. entered into a three-year, $300 million senior unsecured revolving credit facility (the "Facility"). The Facility provides access to loans for working capital and general corporate purposes, and letters of credit to support obligations under insurance and reinsurance agreements and retrocessional agreements. The Facility is subject to various affirmative, negative and financial covenants that Sirius Group considers to be customary for such borrowings, including certain minimum net worth, maximum debt to capitalization, financial strength rating standards, and change in control provisions. As of September 30, 2020, there were no outstanding borrowings under the Facility.

Debt and Standby Letter of Credit Facility Covenants

As of September 30, 2020, Sirius Group was in compliance with all of the covenants under the 2017 SEK Subordinated Notes, the 2016 SIG Senior Notes, the Nordea Bank Finland Abp, London Branch facility, and the DNB Bank ASA, Sweden Branch facility. In addition, as of September 30, 2020, Sirius Group was in compliance with all of the covenants under the Facility.

Interest

Total interest expense incurred by Sirius Group for its indebtedness for the three months ended September 30, 2020 and 2019 was $8.1 million and $7.7 million, respectively. Total interest expense incurred by Sirius Group for its indebtedness for the nine months ended September 30, 2020 and 2019 was $23.8 million and $23.3 million, respectively. Total interest paid by Sirius Group for its indebtedness for the three months ended September 30, 2020 and 2019 was $3.3 million and $2.8 million, respectively. Total interest paid by Sirius Group for its indebtedness for the nine months ended September 30, 2020 and 2019 was $18.5 million and $17.7 million, respectively.

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Income taxes

9 Months Ended

Sep. 30, 2020

Income Tax Disclosure [Abstract]

Income taxes

Income taxes

The Company and its Bermuda-domiciled subsidiaries are not subject to Bermuda income tax under current Bermuda law. In the event there is a change in the current law such that taxes are imposed, the Company and its Bermuda-domiciled subsidiaries would be exempt from such tax until March 31, 2035, pursuant to the Bermuda Exempted Undertakings Tax Protection Act of 1966. The Company has subsidiaries and branches that operate in various other jurisdictions around the world that are subject to tax in the jurisdictions in which they operate. The jurisdictions in which the Company's subsidiaries and branches are subject to tax are Australia, Belgium, Canada, Denmark, Germany, Gibraltar, Hong Kong (China), Ireland, Luxembourg, Malaysia, Shanghai (China), Singapore, Spain, Sweden, Switzerland, the United Kingdom, and the United States.

For the three month period ended September 30, 2020, Sirius Group reported an income tax expense (benefit) of $23.5 million on pre-tax income (loss) of $(80.5) million. The difference between the effective tax rate on income from continuing operations and the Swedish statutory tax rate of 21.4% (the rate at which the majority of Sirius Group's worldwide operations are taxed) is primarily attributable to unrealized investment gains in specific U.S. entities and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate. For the nine month period ended September 30, 2020, Sirius Group reported an income tax expense (benefit) of $19.9 million on pre-tax income (loss) of $(212.6) million. The difference between the effective tax rate for the nine months ended September 30, 2020 and the Swedish statutory rate of 21.4% was primarily attributable to valuation allowances recorded against certain deferred tax assets, unrealized investment gains in specific U.S. entities, and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate.

For the three month period ended September 30, 2019, Sirius Group reported an income tax (benefit) of $(3.7) million on pre-tax (loss) of $(11.3) million. The effective tax rate was higher than the Swedish statutory tax rate of 21.4% primarily because of income recognized in jurisdictions with higher rates than Sweden and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate. For the nine month period ended September 30, 2019, Sirius Group reported an income tax expense of $15.6 million on pre-tax income of $120.3 million. The effective tax rate for the nine months ended September 30, 2019 was lower than the Swedish statutory rate of 21.4% primarily because of income recognized in countries with lower rates than Sweden and adjustments required under applicable GAAP guidance, which are based on the annual estimated effective tax rate.

For purposes of estimating the annual effective tax rate for the nine month periods ended September 30, 2020 and 2019, respectively, Sirius Group took into consideration all year-to-date income and expense items including the change in unrealized investment gains (losses) and realized investment gains (losses) and such items on a forecasted basis for the remainder of each year. Based on applicable GAAP guidance, jurisdictions with a projected loss for the full year where no tax benefit can be recognized are excluded from the estimation of the annual effective tax rate.

The Tax Cuts and Jobs Act ("TCJA") includes a new Base Erosion and Anti-Abuse Minimum Tax ("BEAT") provision, which is essentially a minimum tax that is potentially applicable to certain otherwise deductible payments made by U.S. entities to non-U.S. affiliates, including cross-border interest payments and reinsurance premiums. The statutory BEAT rate is 10% in 2019-2025, and then rises to 12.5% in 2026 and thereafter. The TCJA also includes provisions for Global Intangible Low-Taxed Income ("GILTI") under which taxes on foreign income are imposed on the excess of a deemed return on tangible assets of certain foreign subsidiaries. Consistent with accounting guidance, Sirius Group will treat BEAT as an in period tax charge when incurred in future periods for which no deferred taxes need to be provided and has made an accounting policy election to treat GILTI taxes in a similar manner. No provision for income taxes related to BEAT or GILTI was recorded as of September 30, 2020 and December 31, 2019.

Sirius Group has capital and liquidity in many of its subsidiaries, some of which may reflect undistributed earnings. If such capital or liquidity were to be paid or distributed to the Company or Sirius Group's subsidiaries, as dividends or otherwise, they may be subject to income or withholding taxes. Sirius Group generally intends to operate, and manage its capital and liquidity, in a tax-efficient manner. However, the applicable tax laws in relevant countries are still evolving, including in connection with guidance and proposals from the Organisation for Economic Cooperation and Development. Accordingly, such payments or earnings may be subject to income or withholding tax in jurisdictions where they are not currently taxed or at higher rates of tax than currently taxed, and the applicable tax authorities could attempt to apply income or withholding tax to past earnings or payments.

In April 2020, the European Court of Justice (the “ECJ”) published a decision disallowing the eligibility of an unrelated Gibraltar company for a European Union directive providing relief from withholding taxes on cross-border dividends. More generally, as a result of Brexit, it is projected that Gibraltar companies will cease to be eligible for European Union tax directives from January 1, 2021. The Company has a subsidiary organized in Gibraltar which has been a party to cross-border transactions with affiliates. The Company has assessed the tax consequences of these developments and concluded that they should not materially impact the Company’s provision for income taxes.

Deferred tax asset, net of valuation allowance

Sirius Group's net deferred tax liability, net of the valuation allowance as of September 30, 2020 is $55.1 million. Of the $55.1 million, $25.0 million relates to net deferred tax assets in U.S. subsidiaries, $141.3 million relates to net deferred tax assets in Luxembourg subsidiaries, $213.8 million relates to net deferred tax liabilities in Sweden subsidiaries, and $7.6 million relates to other net deferred tax liability.

Sirius Group records a valuation allowance against deferred tax assets if it becomes more likely than not that all or a portion of a deferred tax asset will not be realized. Changes in valuation allowances from period to period are included in income tax expense in the period of change. In determining whether or not a valuation allowance, or change therein, is warranted, Sirius Group considers factors such as prior earnings history, expected future earnings, carryback and carryforward periods and strategies that if executed would result in the realization of a deferred tax asset. It is possible that certain planning strategies or projected earnings in certain subsidiaries may not be feasible to utilize the entire deferred tax asset, which could result in material changes to Sirius Group's deferred tax assets and tax expense.

Uncertain tax positions

Recognition of the benefit of a given tax position is based upon whether a company determines that it is more likely than not that a tax position will be sustained upon examination based upon the technical merits of the position. In evaluating the more likely than not recognition threshold, Sirius Group must presume that the tax position will be subject to examination by a taxing authority with full knowledge of all relevant information. If the recognition threshold is met, then the tax position is measured at the largest amount of benefit that is more than 50% likely of being realized upon ultimate settlement.

As of September 30, 2020, the total reserve for unrecognized tax benefits is $47.5 million. If Sirius Group determines in the future that its reserves for unrecognized tax benefits on permanent differences and interest and penalties are not needed, the reversal of $47.3 million of such reserves as of September 30, 2020 would be recorded as an income tax benefit and would impact the effective tax rate. If Sirius Group determines in the future that its reserves for unrecognized tax benefits on temporary differences are not needed, the reversal of $0.2 million of such reserves as of September 30, 2020 would not impact the effective tax rate due to deferred tax accounting but would accelerate the payment of cash to the taxing authority. Most of Sirius Group's reserves for unrecognized tax benefits on permanent differences relate to interest deductions denied by the Swedish Tax Authority ("STA"), as described further below.

The STA has denied deductions claimed by two of the Company's Swedish subsidiaries in certain tax years for interest paid on intra-group debt instruments. Sirius Group has challenged the STA's denial in court based on the technical merits. In October 2018, one of the Swedish subsidiaries received an adverse decision from Sweden's Administrative Court, which Sirius Group has appealed. Sirius Group has taken into account this and other relevant developments in applicable Swedish tax law and has established a reserve for this uncertain tax position. As of September 30, 2020, the total amount of such reserve was $46.6 million. In connection with this matter, Sirius Group has also taken into account the Stock Purchase Agreement ("SPA") by which Sirius Group was sold to CMIG International Holding Pte. Ltd ("CMIG International") in 2016 and has recorded an indemnification asset. Pursuant to the SPA, the seller agreed to indemnify the buyer and Sirius Group for, among other things, (1) any additional tax liability in excess of Sirius Group's accounting for uncertain tax positions for tax periods prior to the sale of Sirius Group to CMIG International, and (2) an impairment in Sirius Group's net deferred tax assets resulting from a final determination by a tax authority. CMIG International has informed Sirius Group of their view that CMIG International, rather than Sirius Group, should be entitled to all of the proceeds of such an indemnification claim, while Sirius Group is of the view that it should be entitled to the proceeds of such an indemnification claim to the extent of the book value of the relevant deferred tax assets, and therefore, Sirius Group continues to carry the related indemnification asset on the balance sheet. While Sirius Group intends to continue challenging the STA's denial based on the technical merits (including appealing the adverse court decision received in October 2018), the ultimate resolution of these tax disputes is uncertain and no assurance can be given that there will be no material changes to Sirius Group's operating results or balance sheet in connection with these uncertain tax positions or the related indemnification.

With few exceptions, Sirius Group is no longer subject to U.S. federal, state or non-U.S. income tax examinations by tax authorities for years before 2015.

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Derivatives

9 Months Ended

Sep. 30, 2020

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Derivatives

Derivatives

Interest Rate Cap

Sirius Group entered into an interest rate swap ("Interest Rate Cap") with two financial institutions where it paid an upfront premium and in return receives a series of quarterly payments based on the 3-month London Interbank Offered Rate at the time of payment. The Interest Rate Cap does not qualify for hedge accounting. Changes in fair value are recognized as unrealized gains or losses and are presented within Other revenue. The fair value of the interest rate cap has been estimated using a single broker quote and, accordingly, has been classified as a Level 3 measurement as of September 30, 2020 and December 31, 2019. Collateral held is recorded within short-term investments with an equal amount recognized as a liability to return collateral. Sirius Group's liability to return that collateral is based on the amounts provided by the counterparties and investment earnings thereon. As of September 30, 2020 and December 31, 2019, Sirius Group held collateral balances of $0.1 million and $0.2 million, respectively

Foreign Currency Risk Derivatives

Sirius Group executes foreign currency forwards, call options, swaps, and futures to manage foreign currency exposure. The foreign currency risk derivatives are not designated or accounted for under hedge accounting. Changes in fair value are recognized as unrealized gains or losses and are presented within Net foreign exchange gains. The fair value of the swaps and forwards are estimated using a single broker quote and accordingly, are classified as a Level 3 measurement. The fair value of the futures is widely available and have quoted prices in active markets and accordingly, were classified as a Level 1 measurement. Sirius Group did not provide or hold any collateral associated with the foreign currency risk derivatives.

Weather Derivatives

Sirius Group holds assets and assumes liabilities related to weather and weather contingent risk management products. Weather and weather contingent derivative contracts are entered into with the objective of generating profits in normal climatic conditions. Accordingly, Sirius Group's weather and weather contingent derivatives are not designed to meet the criteria for hedge accounting under GAAP. Sirius Group receives payment of premium at the contract inception in exchange for bearing the risk of variations in a quantifiable weather index. Changes in fair value are recognized as unrealized gains or losses and are presented within Other revenue. The fair value of the weather derivatives was estimated using a broker quote. Because of the significance of the unobservable inputs used to estimate the fair value of Sirius Group's weather risk contracts, the fair value measurements of the contracts are deemed to be Level 3 measurements in the fair value hierarchy as of September 30, 2020 and December 31, 2019. Sirius Group does not provide or hold any collateral associated with the weather derivatives.

Equity Contracts

Sirius Group executes trades in equity futures contracts, call options, and put options to hedge against positions in Common equities. The equity contracts are not designated or accounted for under hedge accounting. Changes in fair value are presented within Net unrealized investment (losses) gains. The fair value of the equity contracts is widely available and have quoted prices in active markets and accordingly, were classified as a Level 1 measurement.

Equity Warrants

Sirius Group holds restricted equity warrants as part of its investment strategy. The equity warrants are not designated or accounted for under hedge accounting. Changes in fair value are presented within Net unrealized investment (losses) gains. The fair value of the equity warrants is estimated using a single broker quote and accordingly, classified as a Level 3 measurement. Sirius Group did not provide or hold any collateral associated with the equity warrants.

The following tables summarize information on the classification and amount of the fair value of derivatives not designated as hedging instruments within the Company's Consolidated Balance Sheets as at September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020						December 31, 2019
Derivatives not designated as hedging instruments	Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)		Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)
Interest rate cap	$	250.0	$	—	$	—	$	250.0	$	—	$	—
Foreign currency swaps	$	40.0	$	0.3	$	—	$	90.0	$	—	$	3.6
Foreign currency forwards	$	225.2	$	0.3	$	—	$	(30.0)	$	2.7	$	5.7
Weather derivatives	$	53.6	$	—	$	3.5	$	110.7	$	7.0	$	—
Equity futures contracts	$	(1.0)	$	—	$	—	$	34.5	$	—	$	—
Foreign currency futures contracts	$	22.3	$	—	$	—	$	—	$	—	$	—
Equity call options	$	34.6	$	2.5	$	—	$	—	$	—	$	—
Equity put options	$	77.3	$	1.9	$	0.1	$	31.0	$	1.3	$	0.2
Foreign currency call options	$	50.6	$	2.2	$	—	$	—	$	—	$	—
Equity warrants	$	0.5	$	0.5	$	—	$	0.4	$	0.4	$	—

(1)Asset derivatives are classified within Other assets within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

(2)Liability derivatives are classified within Other liabilities within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

The following table summarizes information on the classification and net impact on earnings, recognized in the Company's Consolidated Statements of (Loss) Income relating to derivatives during the three and nine months ended September 30, 2020 and 2019:

(Millions)		For the three months ended September 30,				For the nine months ended September 30,
Derivatives not designated as hedging instruments	Classification of gains (losses) recognized in earnings	2020		2019		2020		2019
Interest rate cap	Other revenues	$	—	$	—	$	—	$	(0.2)
Foreign currency swaps	Net foreign exchange (losses) gains	$	(0.9)	$	3.7	$	1.8	$	6.1
Foreign currency forwards	Net foreign exchange (losses) gains	$	(0.4)	$	(7.8)	$	(0.9)	$	(10.8)
Weather derivatives	Other revenues	$	(0.4)	$	1.9	$	(21.8)	$	(3.6)
Equity futures contracts	Net realized investment (losses) gains	$	(0.2)	$	0.1	$	2.4	$	(0.7)
Equity futures contracts	Net unrealized investment gains (losses)	$	(0.1)	$	(0.5)	$	0.4	$	(0.6)
Foreign currency futures contracts	Net foreign exchange (losses) gains	$	0.8	$	—	$	0.1	$	—
Equity put options	Net realized investment (losses) gains	$	1.9	$	(0.8)	$	7.8	$	(0.8)
Equity put options	Net unrealized investment gains (losses)	$	(0.6)	$	0.7	$	0.8	$	0.2
Foreign currency call options	Net foreign exchange (losses) gains	$	1.0	$	—	$	0.8	$	—
Equity warrants	Net unrealized investment gains (losses)	$	(0.1)	$	0.3	$	0.1	$	0.7

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Share-based compensation

9 Months Ended

Sep. 30, 2020

Share-based Payment Arrangement [Abstract]

Share-based compensation

Share-based compensation

Sirius Group's compensation plans include grants for various types of share-based and non-share-based compensation awards to key employees and directors of Sirius Group. During the quarter ended September 30, 2020, all of Sirius Group's outstanding performance shares units ("PSUs") were cancelled and converted into cash-based restricted share units ("RSUs") at the most recent forecasted performance percentage. As of September 30, 2020, Sirius Group's share-based awards consisted of RSUs, restricted stock and options. Additionally, during the quarter ended September 30, 2020, the Company's Compensation Committee approved to offer active employees the opportunity to early settle the 2018 long term incentive award at the recent forecasted performance percentage in cash with the remaining balance of share units converted into replacement cash-based RSUs with extended vesting periods.

Sirius Group recognized $(3.3) million and $3.0 million of compensation expense under the share-based awards during the three months ended September 30, 2020 and 2019, respectively. Sirius Group recognized $0.7 million and $3.1 million of compensation expense under the share-based awards during the nine months ended September 30, 2020 and 2019, respectively. Sirius Group paid $1.9 million and $3.3 million to employees for share-based awards during both the three and the nine months ended September 30, 2020 and 2019, respectively.

The following tables present unrecognized compensation cost associated with unvested awards and weighted average period over which it is expected to be recognized:

(Millions)	September 30, 2020
	RSUs		Stock Options
Unrecognized compensation cost related to unvested awards	$	6.4	$	1.3
Weighted average recognition period (years)	1.3 years		1.5 years

As of September 30, 2019, there were $27.1 million of unrecognized share-based compensation costs, which are expected to be recognized over two to three years.

The following table summarizes outstanding and changes in share-settled awards for the three and nine months ended September 30, 2020:

	Number of Shares
Three months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,274,752	1,374,945
Granted	—	—
Vested	—	—
Forfeited	1,060	—
Unvested, end of period	1,273,692	1,374,945

	Number of Shares
Nine months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,353,852	1,374,945
Granted	—	—
Vested	—	—
Forfeited	80,160	—
Unvested, end of period	1,273,692	1,374,945

In the comparative periods of three and nine months ended September 30, 2019, the Company granted members of the Board of Directors 2,424 restricted shares and 37,039 restricted shares, respectively. For the three months ended September 30, 2019, Sirius Group granted employees 7,059 PSUs and 16,471 RSUs. For the nine months ended September 30, 2019, Sirius Group granted employees 408,370 PSUs, 1,428,185 RSUs, and 1,374,944 stock options. During the three months ended September 30, 2019, Sirius Group's employees forfeited 43,230 PSUs and 25,936 RSUs. During the nine months ended September 30, 2019, Sirius Group's employees forfeited 57,565 PSUs and 71,988 RSUs.

Cash-Settled Awards

During the quarter ended September 30, 2020, Sirius Group recognized an expense of $6.1 million related to newly issued RSUs. Additionally, during the quarter ended September 30, 2020, phantom performance shares of the existing long-term incentive compensation award that was issued in February 2020, were converted into cash-based phantom restricted shares. During the three and nine months ended September 30, 2020, Sirius Group recognized an expense of $1.1 million and $4.2 million, respectively, related to this award.

In addition, in November 2019, Sirius Group issued retention awards to certain key employees that vest and are paid in equal proportions on or prior to March 15, 2020 and on or prior to March 15, 2021, subject to continued employment on the applicable vesting date. In total, the awards issued under this retention program were $13.8 million, of which, $6.9 million was paid on March 15, 2020. During the three and nine months ended September 30, 2020, Sirius Group recognized an expense of $1.6 million and $9.2 million, respectively, in General and administrative expenses.

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Common shareholder's equity, mezzanine equity, and non-controlling interests

9 Months Ended

Sep. 30, 2020

Equity [Abstract]

Common shareholder's equity, mezzanine equity, and non-controlling interests

Common shareholder's equity, mezzanine equity, and non-controlling interests

Common shareholder's equity

The authorized share capital of the Company consists of 500,000,000 Common shares, $0.01 par value per share, and 100,000,000 Preference shares, $0.01 par value per share.

The following table presents changes in the Company's issued and outstanding Common shares for the three and nine months ended September 30, 2020 and 2019, respectively:

	Three months ended September 30,		Nine months ended September 30,
	2020	2019	2020	2019
Common shares:
Shares issued and outstanding, beginning of period	115,299,341	115,296,918	115,299,341	115,151,251
Issuance of shares to directors and employees	—	2,424	—	148,091
Shares issued and outstanding, end of period	115,299,341	115,299,342	115,299,341	115,299,342

Dividends

The Company did not pay dividends to common shareholders during the three and nine months ended September 30, 2020 and 2019.

Mezzanine equity

Series B Preference Shares

Sirius Group has issued 11,901,670 of the 15,000,000 designated Series B preference shares, with a par value of $0.01 per share.

The Series B preference shares rank senior to common shares with respect to dividend rights, rights of liquidation, winding-up, or dissolution of the Company and junior to all of the Company's existing and future policyholder obligations and debt obligations. Without the consent of the holders of the Series B preference shares, the Company may not issue any class or series of shares that rank senior or pari passu with the Series B preference shares as to the payment of dividends or as to distribution of assets upon any voluntary or involuntary liquidation, winding-up or dissolution of the Company, if the aggregate gross proceeds from the issuance of all such senior or pari passu shares equals or exceeds $100 million.

The Company adjusts the carrying value of the Series B preference shares to equal the redemption value at the end of each reporting period. At September 30, 2020 and December 31, 2019, the balance of the Series B preference shares was $197.5 million and $223.0 million, respectively.

Non-controlling interests

Non-controlling interests consist of the ownership interests of non-controlling shareholders in consolidated entities and are presented separately on the balance sheet. At September 30, 2020 and December 31, 2019, Sirius Group's balance sheet included $1.8 million and $2.4 million, respectively, in non-controlling interests.

The following tables show the change in non-controlling interest for the three and nine months ended September 30, 2020 and 2019:

(Millions)	For the three months ended September 30, 2020		For the three months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.5	$	3.0
Net income attributable to non-controlling interests	0.2		0.4
Dividends paid	(1.0)		—
Other, net	0.1		—
Non-controlling interests, end of the period	$	1.8	$	3.4

(Millions)	For the nine months ended September 30, 2020		For the nine months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.4	$	1.7
Net income attributable to non-controlling interests	0.2		1.6
Dividends paid	(1.0)		—
Other, net	0.2		0.1
Non-controlling interests, end of the period	$	1.8	$	3.4

Alstead Re

As of September 30, 2020 and December 31, 2019, Sirius Group recorded non-controlling interest of $1.8 million and $2.3 million, respectively, in Alstead Re Insurance Company ("Alstead Re"). (See Note 17.)

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Earnings per share

9 Months Ended

Sep. 30, 2020

Earnings Per Share [Abstract]

Earnings per share

Earnings per share

Basic earnings per share is computed by dividing net income available to Sirius Group common shareholders by the weighted-average number of common shares outstanding during the period. Diluted earnings per share is computed by dividing net income (loss) available to Sirius Group common shareholders on a diluted basis by the weighted-average number of common shares outstanding adjusted to give effect to potentially dilutive securities.

The Series B preference shares qualify as participating securities, which requires the application of the two-class method to compute both basic and diluted earnings per share. The two-class method is an earnings allocation formula that treats participating securities as having rights to earnings that would otherwise have been available to common shareholders. The Series B preference shares have no obligation to absorb losses of the Company in periods of net loss.

The following table sets forth the computation of basic and diluted earnings per common share for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions, except share and per share information)	2020		2019		2020		2019
Basic earnings per share
Numerator:
Net income	$	(104.0)	$	(7.6)	$	(232.5)	$	104.7
Less: Income attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
Less: Change in carrying value of Series B preference shares	8.7		5.3		25.5		(3.9)
Net income available for dividends out of undistributed earnings	$	(95.5)	$	(2.7)	$	(207.2)	$	99.2
Less: Earnings attributable to Series B preference shares	—		—		—		(9.3)
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Basic earnings per share	$	(0.83)	$	(0.02)	$	(1.80)	$	0.78
Diluted earnings per share
Numerator:
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Add: Change in carrying value of Series B preference shares	—		(5.3)		(25.5)		—
Net income available to Sirius Group common shareholders on a diluted basis	$	(95.5)	$	(8.0)	$	(232.7)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Add: Series B preference shares	—		11,901,670		11,901,670		—
Add: Unvested performance share units and restricted share units	—		—		—		393,280
Weighted average shares outstanding for diluted earnings per share(1)	115,297,945		127,153,523		127,180,867		115,619,222
Diluted earnings per share	$	(0.83)	$	(0.06)	$	(1.83)	$	0.78

(1)For the three months ended September 30, 2020, there were a total of 26,057,275 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the three months ended September 30, 2019, there were 19,537,270 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2020, there were a total of 14,155,605 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2019, there were 31,045,660 potentially dilutive securities excluded from the calculation of Diluted earnings per share.

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Investments in unconsolidated entities

9 Months Ended

Sep. 30, 2020

Investments in unconsolidated entities

Investments in unconsolidated entities

Investments in unconsolidated entitiesSirius Group's investments in unconsolidated entities are included within Other long-term investments and consist of investments in common equity securities or similar instruments, which give Sirius Group the ability to exert significant influence over the investee's operating and financial policies ("equity method eligible unconsolidated entities"). Such investments may be accounted for under either the equity method or, alternatively, Sirius Group may elect to account for them under the fair value option.

The following table presents the components of Other long-term investments as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Equity method eligible unconsolidated entities, at fair value	$	166.8	$	151.9
Other unconsolidated investments, at fair value(1)	221.2		194.9
Total Other long-term investments(2)	$	388.0	$	346.8

(1)Includes Other long-term investments that are not equity method eligible.

(2)There were no investments accounted for using the equity method as of September 30, 2020 and December 31, 2019.

Equity method eligible unconsolidated entities, at fair value

Sirius Group has elected the fair value option to account for its equity method eligible investments accounted for as part of Other long-term investments for consistency of presentation with the rest of its investment portfolio. The following table presents Sirius Group's investments in equity method eligible unconsolidated entities as of September 30, 2020 and December 31, 2019:

	Ownership interest as of
Investee	September 30, 2020		December 31, 2019		Instrument Held
BE Reinsurance Limited	24.9	%	24.9	%	Common shares
BioVentures Investors (Offshore) IV LP	73.0	%	73.0	%	Units
Camden Partners Strategic Fund V (Cayman), LP	39.4	%	39.4	%	Units
Diamond LS I LP	15.6	%	16.0	%	Units
Gateway Fund LP	22.9	%	15.0	%	Units
Monarch	12.8	%	12.8	%	Units
New Energy Capital Infrastructure Credit Fund LP	29.8	%	30.5	%	Units
New Energy Capital Infrastructure Offshore Credit Fund LP	29.8	%	30.5	%	Units
Pie Preferred Stock(1)	30.1	%	30.1	%	Preferred shares
Pie Series B Preferred Stock(1)	23.4	%	22.4	%	Preferred shares
Quintana Energy Partners	21.8	%	21.8	%	Units
Tuckerman Capital V LP	48.3	%	48.3	%	Units
Tuckerman Capital V Co-Investment I LP	48.3	%	48.1	%	Units

(1)Sirius Group holds investments in several financing instruments of Pie Insurance Holdings, Inc.

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Variable interest entities

9 Months Ended

Sep. 30, 2020

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Variable interest entities

Variable interest entitiesSirius Group consolidates the results of operations and financial position of every voting interest entity ("VOE") in which it has a controlling financial interest and VIEs in which it is considered to be the primary beneficiary. The consolidation assessment, including the determination as to whether an entity qualifies as a VOE or VIE, depends on the facts and circumstances surrounding each entity.

Sirius Group has determined that Alstead Re is a VIE for which Sirius Group is the primary beneficiary and is required to consolidate it. The following table presents Alstead Re's assets and liabilities, as classified in the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Assets:
Fixed maturity investments	$	3.8	$	3.9
Short-term investments	0.5		0.5
Cash	0.1		0.1
Total investments	4.3		4.5
Insurance and reinsurance premiums receivable	(0.5)		(0.3)
Funds held by ceding companies	2.3		3.4
Deferred acquisition costs	—		0.3
Other assets	—		—
Total assets	$	6.2	$	7.9
Liabilities
Loss and loss adjustment expense reserves	$	0.3	$	0.5
Unearned insurance and reinsurance premiums	—		0.6
Other liabilities	0.1		0.1
Total liabilities	$	0.4	$	1.2

Sirius Group is a passive investor in certain third-party-managed hedge and private equity funds, some of which are VIEs. Sirius Group is not involved in the design or establishment of these VIEs, nor does it actively participate in the management of the VIEs. The exposure to loss from these investments is limited to the carrying value of the investments at the balance sheet date.

Sirius Group calculates maximum exposure to loss to be (i) the amount invested in the debt or equity of the VIE, (ii) the notional amount of VIE assets or liabilities where Sirius Group has also provided credit protection to the VIE with the VIE as the referenced obligation, and (iii) other commitments and guarantees to the VIE. Sirius Group does not have any VIEs that it sponsors nor any VIEs where it has recourse to it or has provided a guarantee to the VIE interest holders.

The following table presents total assets of unconsolidated VIEs in which Sirius Group holds a variable interest, as well as the maximum exposure to loss associated with these VIEs:

			Maximum Exposure to Loss
(Millions)	Total VIE Assets		On-Balance Sheet		Off-Balance Sheet		Total
September 30, 2020
Other long-term investments(1)	$	254.8	$	117.1	$	7.4	$	124.5
Total at September 30, 2020	$	254.8	$	117.1	$	7.4	$	124.5
December 31, 2019
Other long-term investments(1)	$	257.8	$	102.6	$	16.3	$	118.9
Total at December 31, 2019	$	257.8	$	102.6	$	16.3	$	118.9

(1)Comprised primarily of hedge funds and private equity funds.

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Transactions with related parties

9 Months Ended

Sep. 30, 2020

Related Party Transactions [Abstract]

Transactions with related parties

Transactions with related parties

(Re)insurance contracts

In the normal course of business, Sirius Group enters into insurance and reinsurance contracts with certain of its insurance and MGU affiliates, or their subsidiaries. During the three and nine months ended September 30, 2020, these contracts resulted in gross written premiums of $16.0 million and $84.1 million, respectively. During the three and nine months ended September 30, 2019, these contracts resulted in gross written premiums of $21.7 million and $70.7 million, respectively. As of September 30, 2020 and December 31, 2019, Sirius Group had total receivables due from affiliates of $22.0 million and $16.1 million, respectively. As of both September 30, 2020 and December 31, 2019, Sirius Group had total payables due to affiliates of $0.9 million.

Transaction Matters Letter Agreement

On August 6, 2020, CM Bermuda, the Company, TPRE and CMIG International entered into a Transaction Matters Letter Agreement (the “Transaction Matters Agreement”), pursuant to which, among other things and subject to the terms and conditions thereof, the Company has agreed to pay for and reimburse CMIG International and CM Bermuda for certain legal expenses incurred by CMIG International and CM Bermuda in connection with the Transactions and the related sales process or other discussions between CMIG International, CM Bermuda and the Company occurring on or after March 6, 2020, and TPRE has agreed to assume such remaining payment obligations of the Company following the closing of the Merger. TPRE has also agreed to pay for the fees and expenses payable by CMIG International and CM Bermuda to its financial advisor, Goldman Sachs (Asia) L.L.C., relating to the Transactions. Under the terms of the Transaction Matters Agreement, the Company is not permitted to terminate or threaten to terminate the Merger Agreement following a change by the TPRE board of directors of its recommendation to TPRE’s shareholders in favor of the TPRE Share Issuance without the prior written consent of CM Bermuda and CMIG International. During the quarter ended September 30, 2020, the Company paid $2.2 million for certain legal expenses incurred by CM Bermuda and CMIG International in connection with the Transaction Matters Agreement.

Series B preference shareholders expense reimbursement agreement

On March 27, 2020, the Company entered into an expense reimbursement agreement (the “Agreement”) with each of the holders of the Series B preference shares. Pursuant to the Agreement, the Company agreed to reimburse each of the holders of the Series B preference shares for all reasonable and documented out-of-pocket expenses incurred by them in connection with pursuing a potential negotiated transaction (a “Potential Transaction”) involving the Company or one or more of its subsidiaries on or after January 8, 2020 up to $250,000 for each holder of Series B preference shares together with its affiliates and $1,000,000 in the aggregate with any reimbursement above such amounts requiring the written consent of the Company (but excluding any expenses incurred in connection with the evaluation or enforcement of any rights or obligations of the holders of the Series B preference shares or the Company relating to the preference shares in the Company held by such Series B preference shareholders). In addition, the Company agreed to reimburse the holders of the Series B preference shares for any and all reasonable and documented out-of-pocket attorneys’ fees or other fees payable to third party advisors up to $500,000 in the aggregate to the extent arising out of any litigation, dispute, arbitration or other proceeding commencing after the date of the Agreement that is not brought or commenced by a holder of the Series B preference shares and involves the Company, such Series B preference shareholder's investment in the Company or a Potential Transaction. As of the end of the third quarter 2020, no payments have been requested or made under the Agreement.

Other

Meyer "Sandy" Frucher is the Company's Chairman of the Board of Directors and was also Vice Chairman of Nasdaq, Inc. ("Nasdaq") until December 2019. On January 1, 2020, Mr. Frucher concluded his tenure as Vice Chairman of Nasdaq and assumed the role of Strategic Advisor to Nasdaq. The Company is traded on the Nasdaq Global Select Market and has business transactions that are related to its listing on the exchange under the normal course of business. (See Note 3.)

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Commitments and contingencies

9 Months Ended

Sep. 30, 2020

Commitments and Contingencies Disclosure [Abstract]

Commitments and contingencies

Commitments and contingencies

Legal Proceedings

Sirius Group, and the insurance and reinsurance industry in general, are routinely subject to claims related litigation and arbitration in the normal course of business, as well as litigation and arbitration that do not arise from, or are directly related to, claims activity. Sirius Group's estimates of the costs of settling matters routinely encountered in claims activity are reflected in the reserves for unpaid loss and LAE. (See Note 5.)

Sirius Group considers the requirements of ASC 450, Contingencies ("ASC 450"), when evaluating its exposure to non-claims related litigation and arbitration. ASC 450 requires that accruals be established for litigation and arbitration if it is probable that a loss has been incurred and it can be reasonably estimated. ASC 450 also requires that litigation and arbitration be disclosed if it is probable that a loss has been incurred or if there is a reasonable possibility that a loss may have been incurred. Management has considered all pending and/or threatened non-claims related litigation and has not identified any matters triggering disclosure under ASC 450.

Leases

Sirius Group leases office space and equipment under various noncancelable operating lease agreements. The average life of the office leases is 7 years and the equipment leases is 3 years.

During the three and nine months ended September 30, 2020, Sirius Group recognized operating lease expense of $3.0 million and $9.0 million, respectively, including property taxes and routine maintenance expense as well as rental expenses related to short term leases. During the three and nine months ended September 30, 2019, Sirius Group recognized operating lease expense of $3.4 million and $9.3 million, respectively, including property taxes and routine maintenance expense as well as rental expenses related to short term leases.

As of September 30, 2020 and December 31, 2019, Sirius Group had $27.1 million and $27.4 million of operating lease right-of-use assets, respectively, included in Other assets. As of September 30, 2020 and December 31, 2019, Sirius Group had $29.0 million and $29.3 million of operating lease liability, respectively, included in Other liabilities.

The following table presents the lease balances within the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(millions)	Balance Sheet Classification	September 30, 2020	December 31, 2019
Operating lease right-of-use assets	Other assets	$27.1	$27.4
Current lease liabilities	Other liabilities	$9.2	$8.3
Non-current lease liabilities	Other liabilities	$19.8	$21.0

The following table presents weighted average remaining lease term and weighted average discount rate as of September 30, 2020:

Weighted average lease term (years) as at September 30, 2020
Leased offices	7 years
Leased equipment	3 years
Weighted average discount rate:
Leased offices	3.3	%
Leased equipment	3.3	%

The following table presents future annual minimum rental payments required under non-cancellable leases and the present value discount to arrive at total lease liability as of September 30, 2020:

(Millions)	Future Payments
2020	$	2.4
2021	9.6
2022	9.5
2023	5.7
2024	2.3
2025 and after	1.2
Total future annual minimum rental payments as of September 30, 2020	30.7
Less: present value discount	(1.7)
Total lease liability as of September 30, 2020	$	29.0

As of September 30, 2020, the Company's future operating lease obligations that have not yet commenced are immaterial.

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Summary of significant accounting policies (Policies)

9 Months Ended

Sep. 30, 2020

Accounting Policies [Abstract]

Basis of presentation

Basis of presentation

The accompanying Unaudited Consolidated Financial Statements at September 30, 2020, have been prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP") and the rules and regulations of the U.S. Securities and Exchange Commission ("SEC") for interim financial information. The accompanying Unaudited Consolidated Financial Statements present the consolidated results of operations, financial condition, and cash flows of the Company and its subsidiaries and those entities in which the Company has control and a majority economic interest as well as those variable interest entities ("VIEs") that meet the requirements for consolidation. All significant intercompany transactions have been eliminated in consolidation.

These Unaudited Consolidated Financial Statements do not include all disclosures normally included in annual financial statements prepared in accordance with GAAP and should be read in conjunction with the Audited Consolidated Financial Statements and the related notes for the year ended December 31, 2019. The consolidated financial information as of December 31, 2019 included herein has been derived from the Audited Consolidated Financial Statements as of December 31, 2019.

Effective January 1, 2020, the Company changed its reportable segments. The change in reportable segments had no impact on the Company’s historical consolidated financial positions, results of operations or cash flows as previously reported. Where applicable, all prior periods presented have been revised to conform to this new presentation.

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities as of the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates. In the opinion of management, the accompanying Unaudited Consolidated Financial Statements reflect all adjustments (consisting of normally recurring accruals) necessary for a fair statement of results on an interim basis. Tabular dollar amounts are in millions, with the exception of share and per share amounts. All amounts are reported in U.S. dollars, except where noted otherwise.

Recently adopted changes in accounting principles

Recently adopted changes in accounting principles

Credit losses

Effective January 1, 2020, Sirius Group adopted Accounting Standards Update ("ASU") 2016-13, Measurement of Credit Losses on Financial Instruments (ASC 326), which establishes new guidance for the recognition of credit losses for financial assets measured at amortized cost ("current expected credit losses" or "CECL"). The guidance applies to financial assets that have the contractual right to receive cash, including reinsurance receivables and recoverables and requires reporting entities to estimate the credit losses expected over the life of a credit exposure using historical information, current information and reasonable and supportable forecasts that affect the collectability of the financial asset. The expected credit losses, and subsequent adjustments to such losses, are recorded through an allowance account that is deducted from the amortized cost basis of the financial asset, with the net carrying value of the financial asset presented on the consolidated balance sheet at the amount expected to be collected. Sirius Group adopted the new guidance using a modified retrospective transition method through a cumulative-effect adjustment to retained earnings.

As a result of the adoption of the new guidance, Sirius Group estimated a total CECL allowance of $14.9 million. The adoption of this guidance did not materially impact our results of operations or cash flows. Due to the adoption of the standard using the retrospective cumulative-effect adjustment method, the Company recorded a $(6.8) million cumulative-effect adjustment net of taxes to its opening retained earnings. (See Note 7.)

Fair Value Measurement Disclosures

Effective January 1, 2020, Sirius Group adopted ASU 2018-13, Fair Value Measurement (Topic 820): Disclosure Framework—Changes to the Disclosure Requirements for Fair Value Measurement, which modifies the disclosure requirements of fair value measurements. The adoption of this guidance did not have any impact on the consolidated financial statements but expanded disclosure of the ranges and weighted averages of significant unobservable inputs used in Level 3 fair values. (See Note 9.)

Simplifying the Accounting for Income Taxes

Effective January 1, 2020, Sirius Group adopted ASU 2019-12, Income Taxes (Topic 740): Simplifying the Accounting for Income Taxes, which eliminates certain exceptions, and clarifies and simplifies certain aspects of accounting for income taxes. Sirius Group has fully adopted all provisions of the guidance with consideration of the various transition methods.

Sirius Group adopted the removal of the exception to the general methodology for calculating income taxes in an interim period when a year-to-date loss exceeds the anticipated loss for the year. The removal of this exception allowed Sirius Group to record a benefit for a year-to-date loss in excess of its forecasted loss in certain jurisdictions. The removal of this exception was applied prospectively to the Income tax benefit (expense) line on the Consolidated Statements of (Loss) Income.

Sirius Group adopted all other provisions in the guidance, including the requirement for an entity to recognize a franchise tax (or similar tax) that is partially based on income as an income-based tax and account for any incremental amount incurred as a non-income-based tax through a cumulative-effect adjustment to retained earnings. These provisions did not have a material impact on the Consolidated Financial Statements or were not applicable to Sirius Group.

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Segment information (Tables)

9 Months Ended

Sep. 30, 2020

Segment Reporting [Abstract]

Summary of segment results

The following tables summarize the segment results for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	248.2		$	88.8		$	22.6		$	(3.6)	$	—	$	356.0
Net written premiums	$	192.2		$	72.2		$	20.5		$	(2.6)	$	—	$	282.3
Net earned insurance and reinsurance premiums	$	243.5		$	114.3		$	17.2		$	(2.4)	$	—	$	372.6
Loss and allocated LAE(1)	(194.5)			(84.6)			(11.1)			(1.1)		—		(291.3)
Insurance and reinsurance acquisition expenses	(51.8)			(36.6)			(4.0)			(0.8)		9.6		(83.6)
Technical (loss) profit	(2.8)			(6.9)			2.1			(4.3)		9.6		(2.3)
Unallocated LAE(2)	(7.7)			(0.5)			(0.2)			(1.0)		(4.7)		(14.1)
Other underwriting expenses	(25.3)			(5.7)			(4.3)			(1.3)		(4.7)		(41.3)
Underwriting (loss) income	(35.8)			(13.1)			(2.4)			(6.6)		0.2		(57.7)
Service fee revenue(3)	—			26.3			—			0.9		(10.7)		16.5
Managing general underwriter unallocated LAE	—			(5.8)			—			—		5.8		—
Managing general underwriter other underwriting expenses	—			(4.7)			—			—		4.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(11.0)			—			(0.9)		—		(11.9)
Underwriting (loss) income, including net service fee income	(35.8)			(8.3)			(2.4)			(6.6)		—		(53.1)
Net investment income														1.7
Net realized investment gains														(3.8)
Net unrealized investment gains														31.2
Net foreign exchange (losses)														(21.3)
Other revenue(5)														(0.7)
General and administrative expenses(6)														(22.5)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(8.1)
Pre-tax (loss)														$	(80.5)
Underwriting Ratios(7)
Loss ratio	83.0		%	74.5		%	65.7		%	NM		NM		82.0		%
Acquisition expense ratio	21.3		%	32.0		%	23.3		%	NM		NM		22.4		%
Other underwriting expense ratio	10.4		%	5.0		%	25.0		%	NM		NM		11.1		%
Combined ratio(7)	114.7		%	111.5		%	114.0		%	NM		NM		115.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	256.3		$	137.4		$	17.9		$	2.1	$	—	$	413.7
Net written premiums	$	202.6		$	104.6		$	14.3		$	0.8	$	—	$	322.3
Net earned insurance and reinsurance premiums	$	249.5		$	115.1		$	9.1		$	0.5	$	—	$	374.2
Loss and allocated LAE(1)	(261.7)			(63.6)			(8.2)			(0.9)		—		(334.4)
Insurance and reinsurance acquisition expenses	(54.3)			(32.5)			(2.0)			(0.1)		13.8		(75.1)
Technical (loss) profit	(66.5)			19.0			(1.1)			(0.5)		13.8		(35.3)
Unallocated LAE(2)	(8.4)			(2.0)			(0.1)			(0.2)		(3.5)		(14.2)
Other underwriting expenses	(20.8)			(6.8)			(2.7)			(1.4)		(3.7)		(35.4)
Underwriting (loss) income	(95.7)			10.2			(3.9)			(2.1)		6.6		(84.9)
Service fee revenue(3)	—			31.0			—			—		(14.6)		16.4
Managing general underwriter unallocated LAE	—			(4.3)			—			—		4.3		—
Managing general underwriter other underwriting expenses	—			(3.7)			—			—		3.7		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(15.1)			—			(1.2)		—		(16.3)
Underwriting (loss) income, including net service fee income	(95.7)			18.1			(3.9)			(3.3)		—		(84.8)
Net investment income														22.8
Net realized investment gains														15.3
Net unrealized investment gains														53.9
Net foreign exchange gains														4.9
Other revenue(5)														(0.1)
General and administrative expenses(6)														(11.7)
Intangible asset amortization expenses														(3.9)
Interest expense on debt														(7.7)
Pre-tax (loss)														$	(11.3)
Underwriting Ratios(7)
Loss ratio	108.3		%	57.0		%	91.2		%	NM		NM		93.2		%
Acquisition expense ratio	21.8		%	28.2		%	22.0		%	NM		NM		20.1		%
Other underwriting expense ratio	8.3		%	5.9		%	29.7		%	NM		NM		9.5		%
Combined ratio(7)	138.4		%	91.1		%	142.9		%	NM		NM		122.8		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

The following tables summarize the segment results for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	927.0		$	434.6		$	68.9		$	65.7	$	—	$	1,496.2
Net written premiums	$	758.1		$	334.9		$	59.5		$	65.7	$	—	$	1,218.2
Net earned insurance and reinsurance premiums	$	719.4		$	345.4		$	45.2		$	67.1	$	—	$	1,177.1
Loss and allocated LAE(1)	(600.2)			(234.5)			(29.2)			(61.2)		—		(925.1)
Insurance and reinsurance acquisition expenses	(156.4)			(98.9)			(10.4)			(0.9)		30.2		(236.4)
Technical (loss) profit	(37.2)			12.0			5.6			5.0		30.2		15.6
Unallocated LAE(2)	(17.9)			(2.8)			(0.4)			(11.8)		(14.8)		(47.7)
Other underwriting expenses	(67.1)			(18.0)			(12.4)			(3.7)		(14.4)		(115.6)
Underwriting (loss) income	(122.2)			(8.8)			(7.2)			(10.5)		1.0		(147.7)
Service fee revenue(3)	—			85.3			—			0.9		(33.4)		52.8
Managing general underwriter unallocated LAE	—			(18.0)			—			—		18.0		—
Managing general underwriter other underwriting expenses	—			(14.4)			—			—		14.4		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(36.2)			—			(3.8)		—		(40.0)
Underwriting (loss) income, including net service fee income	(122.2)			7.9			(7.2)			(13.4)		—		(134.9)
Net investment income														30.0
Net realized investment gains														23.6
Net unrealized investment (losses)														(3.9)
Net foreign exchange (losses)														(18.9)
Other revenue(5)														(22.5)
General and administrative expenses(6)														(50.4)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.8)
Pre-tax (loss)														$	(212.6)
Underwriting Ratios(7)
Loss ratio	85.9		%	68.7		%	65.5		%	NM		NM		82.6		%
Acquisition expense ratio	21.7		%	28.6		%	23.0		%	NM		NM		20.1		%
Other underwriting expense ratio	9.3		%	5.2		%	27.4		%	NM		NM		9.8		%
Combined ratio(7)	116.9		%	102.5		%	115.9		%	NM		NM		112.5		%
Goodwill and intangible assets(8)	$	—		$	560.7		$	—		$	8.1	$	—	$	568.8

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of losses from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance			Global A&H			U.S. Specialty			Runoff & Other		Corporate Eliminations		Total
Gross written premiums	$	1,008.4		$	459.5		$	50.5		$	4.7	$	—	$	1,523.1
Net written premiums	$	805.2		$	360.1		$	42.0		$	1.5	$	—	$	1,208.8
Net earned insurance and reinsurance premiums	$	705.7		$	330.0		$	19.9		$	1.2	$	—	$	1,056.8
Loss and allocated LAE(1)	(558.0)			(198.6)			(14.7)			(4.4)		—		(775.7)
Insurance and reinsurance acquisition expenses	(149.9)			(95.1)			(4.5)			(2.6)		36.7		(215.4)
Technical (loss) profit	(2.2)			36.3			0.7			(5.8)		36.7		65.7
Unallocated LAE(2)	(17.1)			(5.5)			(0.2)			(0.9)		(11.1)		(34.8)
Other underwriting expenses	(64.0)			(18.8)			(7.6)			(4.6)		(11.2)		(106.2)
Underwriting (loss) income	(83.3)			12.0			(7.1)			(11.3)		14.4		(75.3)
Service fee revenue(3)	—			97.6			—			—		(39.3)		58.3
Managing general underwriter unallocated LAE	—			(13.7)			—			—		13.7		—
Managing general underwriter other underwriting expenses	—			(11.2)			—			—		11.2		—
General and administrative expenses, MGU + Runoff & Other(4)	—			(46.3)			—			(3.0)		—		(49.3)
Underwriting (loss) income, including net service fee income	(83.3)			38.4			(7.1)			(14.3)		—		(66.3)
Net investment income														67.3
Net realized investment gains														39.9
Net unrealized investment gains														143.4
Net foreign exchange gains														9.4
Other revenue(5)														(7.0)
General and administrative expenses(6)														(31.3)
Intangible asset amortization expenses														(11.8)
Interest expense on debt														(23.3)
Pre-tax income														$	120.3
Underwriting Ratios(7)
Loss ratio	81.5		%	61.8		%	74.9		%	NM		NM		76.7		%
Acquisition expense ratio	21.2		%	28.8		%	22.6		%	NM		NM		20.4		%
Other underwriting expense ratio	9.1		%	5.7		%	38.2		%	NM		NM		10.0		%
Combined ratio(7)	111.8		%	96.3		%	135.7		%	NM		NM		107.1		%
Goodwill and intangible assets(8)	$	—		$	576.1		$	—		$	8.1	$	—	$	584.2

(1)Loss and allocated loss adjustment expenses ("LAE") are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(2)Unallocated LAE are part of Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income (the sum of Loss and allocated LAE and Unallocated LAE is equal to Loss and loss adjustment expenses on the Consolidated Statements of (Loss) Income).

(3)Service fee revenue is part of Other revenue on the Consolidated Statements of (Loss) Income (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(4)General and administrative expenses, MGU + Runoff & Other is part of General and administrative expenses on the Consolidated Statements of (Loss) Income (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(5)Other revenue is presented net of Service fee revenue and is comprised mainly of a change in contingent consideration (see Note 9) and gains (losses) from derivatives (see Note 12) (the sum of Service fee revenue and Other revenue is equal to Other revenue on the Consolidated Statements of (Loss) Income).

(6)General and administrative expenses are presented net of General and administrative expenses, MGU + Runoff & Other (the sum of General and administrative expenses, MGU + Runoff & Other and General and administrative expenses is equal to General and administrative expenses on the Consolidated Statements of (Loss) Income).

(7)Ratios considered not meaningful ("NM") to Runoff & Other and Corporate Eliminations.

(8)Sirius Group does not allocate its assets by segment, with the exception of goodwill and intangible assets.

Summary information regarding net premiums written by client location and underwriting location by reportable segment

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the three months ended September 30, 2020 and 2019:

	For the three months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	86.7	$	57.3	$	20.5	$	0.8	$	165.3
Europe	49.3		7.0		—		—		56.3
Canada, the Caribbean, Bermuda and Latin America	25.9		2.3		—		(3.6)		24.6
Asia and Other	30.3		5.6		—		0.2		36.1
Total net written premiums by client location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3
Total net written premiums by underwriting location:
United States	$	53.8	$	28.6	$	20.5	$	0.8	$	103.7
Europe	84.9		43.4		—		—		128.3
Canada, the Caribbean, Bermuda and Latin America	42.8		0.2		—		(3.6)		39.4
Asia and Other	10.7		—		—		0.2		10.9
Total net written premiums by underwriting location for the three months ended September 30, 2020	$	192.2	$	72.2	$	20.5	$	(2.6)	$	282.3

	For the three months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	112.8	$	87.6	$	14.3	$	0.7	$	215.4
Europe	29.7		5.8		—		(0.1)		35.4
Canada, the Caribbean, Bermuda and Latin America	24.5		3.7		—		0.1		28.3
Asia and Other	35.6		7.5		—		0.1		43.2
Total net written premiums by client location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3
Total net written premiums by underwriting location:
United States	$	20.2	$	36.9	$	—	$	0.7	$	57.8
Europe	81.9		68.1		14.3		—		164.3
Canada, the Caribbean, Bermuda and Latin America	91.3		(0.6)		—		—		90.7
Asia and Other	9.2		0.2		—		0.1		9.5
Total net written premiums by underwriting location for the three months ended September 30, 2019	$	202.6	$	104.6	$	14.3	$	0.8	$	322.3

The following tables provide summary information regarding total net written premiums by client location and underwriting location by reportable segment for the nine months ended September 30, 2020 and 2019:

	For the nine months ended September 30, 2020
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	297.9	$	288.7	$	59.5	$	68.4	$	714.5
Europe	264.8		19.4		—		0.4		284.6
Canada, the Caribbean, Bermuda and Latin America	74.2		10.1		—		(3.6)		80.7
Asia and Other	121.2		16.7		—		0.5		138.4
Total net written premiums by client location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2
Total net written premiums by underwriting location:
United States	$	162.5	$	185.7	$	59.5	$	68.4	$	476.1
Europe	376.3		149.4		—		0.4		526.1
Canada, the Caribbean, Bermuda and Latin America	174.6		(0.3)		—		(3.6)		170.7
Asia and Other	44.7		0.1		—		0.5		45.3
Total net written premiums by underwriting location for the nine months ended September 30, 2020	$	758.1	$	334.9	$	59.5	$	65.7	$	1,218.2

	For the nine months ended September 30, 2019
(Expressed in millions of U.S. dollars)	Global Reinsurance		Global A&H		U.S. Specialty		Runoff & Other		Total
Total net written premiums by client location:
United States	$	382.1	$	301.2	$	42.0	$	1.0	$	726.3
Europe	207.7		18.9		—		0.1		226.7
Canada, the Caribbean, Bermuda and Latin America	70.2		10.7		—		0.1		81.0
Asia and Other	145.2		29.3		—		0.3		174.8
Total net written premiums by client location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8
Total net written premiums by underwriting location:
United States	$	57.8	$	136.0	$	—	$	1.0	$	194.8
Europe	368.0		190.1		42.0		0.2		600.3
Canada, the Caribbean, Bermuda and Latin America	334.4		33.4		—		—		367.8
Asia and Other	45.0		0.6		—		0.3		45.9
Total net written premiums by underwriting location for the nine months ended September 30, 2019	$	805.2	$	360.1	$	42.0	$	1.5	$	1,208.8

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Reserves for unpaid losses and loss adjustment expenses (Tables)

9 Months Ended

Sep. 30, 2020

Insurance [Abstract]

Summary of the loss and LAE reserve activities

The following table summarizes the loss and LAE reserve activities of Sirius Group for the three and nine months ended September 30, 2020 and 2019:

	Three months ended September 30,				Nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross beginning balance	$	2,515.1	$	2,023.3	$	2,331.5	$	2,016.7
Less beginning reinsurance recoverable on unpaid losses	(442.2)		(357.4)		(410.3)		(350.2)
Net loss and LAE reserve balance	2,072.9		1,665.9		1,921.2		1,666.5
Losses and LAE incurred relating to:
Current year losses	305.5		342.2		967.5		723.6
Prior years losses	(0.1)		6.4		5.3		86.9
Total net incurred losses and LAE	305.4		348.6		972.8		810.5
Foreign currency translation adjustment to net loss and LAE reserves	20.8		(15.3)		12.2		(15.3)
Accretion of fair value adjustment to net loss and LAE reserves	0.1		—		0.1		0.1
Loss and LAE paid relating to:
Current year losses	81.6		97.7		149.2		254.8
Prior years losses	127.2		108.0		566.7		413.5
Total loss and LAE payments	208.8		205.7		715.9		668.3
Net ending balance	2,190.4		1,793.5		2,190.4		1,793.5
Plus ending reinsurance recoverable on unpaid losses	482.5		392.9		482.5		392.9
Gross ending balance	$	2,672.9	$	2,186.4	$	2,672.9	$	2,186.4

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Allowance for expected credit losses (Tables)

9 Months Ended

Sep. 30, 2020

Credit Loss [Abstract]

Summary of allowance for expected credit losses

As of September 30, 2020, Sirius Group's allowance for expected credit losses is as follows:

(in millions)	Gross Assets in Scope		Allowance for Expected Credit Losses
Premiums receivable & Funds held by ceding companies	$	1,033.1	$	10.6
Reinsurance recoverable on unpaid and paid loss	552.9		3.9
MGU Trade receivables(1)	17.2		0.4
Total as of September 30, 2020	$	1,603.2	$	14.9

(1) Included as part of Other assets on the Consolidated Balance Sheet

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Investment securities (Tables)

9 Months Ended

Sep. 30, 2020

Investments, Debt and Equity Securities [Abstract]

Schedule of net investment income

Net investment income for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	10.1	$	12.8	$	31.5	$	40.0
Short-term investments	0.6		4.1		5.2		12.0
Equity securities	0.8		2.7		5.5		12.5
Other long-term investments(1)(2)	(6.0)		5.2		(2.7)		12.3
Total investment income	5.5		24.8		39.5		76.8
Investment expenses	(3.8)		(2.0)		(9.5)		(9.5)
Net investment income	$	1.7	$	22.8	$	30.0	$	67.3

(1)Includes $(8.1) and $0.0 of interest on funds held for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $(7.5) and $0.6 of interest on funds held for the nine months ended September 30, 2020 and 2019, respectively.

Schedule of net realized and unrealized investment gains (losses)

Net realized and unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Gross realized gains	$	41.3	$	22.1	$	140.7	$	63.1
Gross realized (losses)	(45.1)		(6.8)		(117.1)		(23.2)
Net realized (losses) gains on investments(1)(2)	(3.8)		15.3		23.6		39.9
Net unrealized gains (losses) on investments(3)(4)	31.2		53.9		(3.9)		143.4
Net realized and unrealized gains (losses) on investments	$	27.4	$	69.2	$	19.7	$	183.3

(1)Includes $(11.2) and $14.0 of realized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(2)Includes $5.4 and $34.5 of realized gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

(3)Includes $(16.7) and $33.9 of unrealized (losses) gains due to foreign currency for the three months ended September 30, 2020 and 2019, respectively.

(4)Includes $(29.8) and $51.7 of unrealized (losses) gains due to foreign currency for the nine months ended September 30, 2020 and 2019, respectively.

Schedule of net realized investment gains (losses)

Net realized investment gains for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(0.4)	$	7.5	$	17.3	$	22.4
Equity securities	1.0		1.7		(5.0)		(0.1)
Short-term investments	(6.2)		6.5		(2.4)		9.7
Derivative instruments	1.8		(0.7)		10.3		(1.5)
Other long-term investments	—		0.3		3.4		9.4
Net realized investment (losses) gains	$	(3.8)	$	15.3	$	23.6	$	39.9

Schedule of net unrealized investment gains (losses)

Net unrealized investment gains (losses) for the three and nine months ended September 30, 2020 and 2019 consisted of the following:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	(1.0)	$	31.4	$	2.2	$	72.1
Equity securities	18.5		12.0		(33.7)		50.4
Short-term investments	(3.1)		4.6		(3.2)		6.4
Derivative instruments	(0.8)		0.9		1.4		0.2
Other long-term investments	17.6		5.0		29.4		14.3
Net unrealized investment gains (losses)	$	31.2	$	53.9	$	(3.9)	$	143.4

The following table summarizes the amount of total gains (losses) included in earnings attributable to unrealized investment gains (losses) for Level 3 investments for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions)	2020		2019		2020		2019
Fixed maturity investments	$	—	$	—	$	0.3	$	—
Other long-term investments	8.2		(0.3)		3.1		10.1
Total unrealized investment gains (losses) – Level 3 investments	$	8.2	$	(0.3)	$	3.4	$	10.1

Schedule of investment securities and other long-term investments

The cost or amortized cost, gross unrealized investment gains (losses), net foreign currency gains (losses), and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	471.4	$	10.0	$	(0.8)	$	1.3	$	481.9
Asset-backed securities	740.0		8.4		(12.4)		(4.4)		731.6
Residential mortgage-backed securities	393.8		22.2		(0.9)		1.4		416.5
U.S. government and government agency	119.2		0.8		—		(3.6)		116.4
Commercial mortgage-backed securities	120.8		3.1		(1.7)		—		122.2
Non-U.S. government and government agency	71.4		0.4		(0.1)		(0.6)		71.1
Preferred stocks	14.9		3.1		(0.1)		—		17.9
U.S. States, municipalities and political subdivision	1.2		0.1		—		—		1.3
Total fixed maturity investments	$	1,932.7	$	48.1	$	(16.0)	$	(5.9)	$	1,958.9

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains (losses)		Fair value
Corporate debt securities	$	458.6	$	5.2	$	(1.2)	$	11.5	$	474.1
Asset-backed securities	489.4		1.4		(3.9)		(0.1)		486.8
Residential mortgage-backed securities	426.2		10.5		(1.4)		3.6		438.9
U.S. government and government agency	111.5		0.7		(0.4)		(1.3)		110.5
Commercial mortgage-backed securities	88.5		0.9		(0.6)		0.2		89.0
Non-U.S. government and government agency	63.7		—		(0.7)		—		63.0
Preferred stocks	17.0		—		—		—		17.0
U.S. States, municipalities and political subdivision	1.7		—		—		—		1.7
Total fixed maturity investments	$	1,656.6	$	18.7	$	(8.2)	$	13.9	$	1,681.0

The cost or amortized cost, gross unrealized investment gains and losses, net foreign currency gains, and fair values of Sirius Group's equity securities and other long-term investments as of September 30, 2020 and December 31, 2019, were as follows:

	September 30, 2020
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	170.0	$	27.8	$	(39.7)	$	0.6	$	158.7
Other long-term investments	$	327.5	$	75.5	$	(24.4)	$	9.4	$	388.0

	December 31, 2019
(Millions)	Cost or amortized cost		Gross unrealized gains		Gross unrealized (losses)		Net foreign currency gains		Fair value
Equity securities	$	379.2	$	55.6	$	(37.3)	$	7.7	$	405.2
Other long-term investments	$	315.4	$	49.9	$	(29.3)	$	10.8	$	346.8

Equity securities at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Fixed income mutual funds	$	1.8	$	175.3
Common stocks	170.1		228.1
Other equity securities(1)	(13.2)		1.8
Total Equity securities	$	158.7	$	405.2

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

Other long-term investments at fair value consisted of the following as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Hedge funds and private equity funds	$	301.1	$	269.0
Limited liability companies and private equity securities	86.9		77.8
Total other long-term investments	$	388.0	$	346.8

Schedule of fixed maturity investment by contractual maturity

The cost or amortized cost and fair value of Sirius Group's fixed maturity investments as of September 30, 2020 and December 31, 2019 are presented below by contractual maturity. Actual maturities could differ from contractual maturities because borrowers may have the right to call or prepay certain obligations with or without call or prepayment penalties.

	September 30, 2020				December 31, 2019
(Millions)	Cost or amortized cost		Fair value		Cost or amortized cost		Fair value
Due in one year or less	$	203.2	$	212.2	$	85.0	$	88.4
Due after one year through five years	406.7		404.4		479.1		490.3
Due after five years through ten years	41.0		41.7		46.3		46.0
Due after ten years	12.3		12.4		25.1		24.6
Mortgage-backed and asset-backed securities	1,254.6		1,270.3		1,004.1		1,014.7
Preferred stocks	14.9		17.9		17.0		17.0
Total	$	1,932.7	$	1,958.9	$	1,656.6	$	1,681.0

Schedule of ratings and fair value of fixed maturity investments

The following table summarizes the ratings and fair value of fixed maturity investments held in Sirius Group's investment portfolio as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
AAA	$	807.8	$	559.8
AA	734.4		724.3
A	213.7		219.0
BBB	99.2		95.8
Other	103.8		82.1
Total fixed maturity investments(1)	$	1,958.9	$	1,681.0

(1)Credit ratings are assigned based on the following hierarchy: 1) Standard & Poor's ("S&P") and 2) Moody's Investors Service ("Moody's").

Summary of investment securities by investment objective and sector

The following table summarizes investments in hedge funds and private equity interests by investment objective and sector as of September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair value		Unfunded commitments		Fair value		Unfunded commitments
Hedge funds:
Long/short multi-sector	$	54.9	$	—	$	53.0	—
Distressed mortgage credit	66.3		—		51.6		—
Private credit	22.1		—		21.5		—
Multi-sector	5.8		—		—		—
Other	1.2		—		1.4		—
Total hedge funds	150.3		—		127.5		—
Private equity funds:
Energy infrastructure & services	56.6		30.7		53.6		34.6
Multi-sector	13.4		8.1		8.7		7.8
Healthcare	29.1		6.3		25.9		10.4
Life settlement	20.6		—		23.9		—
Manufacturing/Industrial	27.7		—		27.6		3.9
Private equity secondaries	0.6		0.8		0.6		0.8
Other	2.8		1.8		1.2		2.6
Total private equity funds	150.8		47.7		141.5		60.1
Total hedge and private equity funds included in Other long-term investments	$	301.1	$	47.7	$	269.0	$	60.1

Schedule of redemption frequency and advance notice period requirements for investments

The following summarizes the September 30, 2020 fair value of hedge funds subject to restrictions on redemption frequency and advance notice period requirements for investments in active hedge funds:

	Notice Period
Redemption Frequency (Millions)	1-29 days notice		30-59 days notice		60-89 days notice		90-119 days notice		120+ days notice		Total
Monthly	$	5.8	$	—	$	30.5	$	—	$	—	$	36.3
Quarterly	—		0.6		24.4		66.3		—		$	91.3
Semi-annual	—		—		0.3		—		—		$	0.3
Annual	—		—		—		0.3		22.1		$	22.4
Total	$	5.8	$	0.6	$	55.2	$	66.6	$	22.1	$	150.3

Schedule of investment securities by lock-up period.

As of September 30, 2020, investments in private equity funds were subject to lock-up periods as follows:

(Millions)	1 - 3 years		3 – 5 years		5 – 10 years		Total
Private Equity Funds – expected lock up period remaining	$	53.9	$	19.0	$	77.9	$	150.8

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Fair value measurements (Tables)

9 Months Ended

Sep. 30, 2020

Fair Value Disclosures [Abstract]

Summary of financial assets and liabilities measured at fair value

The following tables summarize Sirius Group's financial assets and liabilities measured at fair value as of September 30, 2020 and December 31, 2019 by level:

	September 30, 2020
(Millions)	Fair Value		Level 1 Inputs		Level 2 Inputs		Level 3 Inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	116.4	$	115.4	$	1.0	$	—
Corporate debt securities	481.9		—		481.9		—
Residential mortgage-backed securities	416.5		—		416.5		—
Asset-backed securities	731.6		—		731.6		—
Commercial mortgage-backed securities	122.2		—		122.2		—
Non-U.S. government and government agency	71.1		20.8		50.3		—
Preferred stocks	17.9		—		15.3		2.6
U.S. States, municipalities, and political subdivision	1.3		—		1.3		—
Total fixed maturity investments	1,958.9		136.2		1,820.1		2.6
Equity securities:
Fixed income mutual funds	1.8		1.8		—		—
Common stocks	170.1		170.1		—		—
Other equity securities(1)	(13.2)		(16.9)		3.7		—
Total equity securities	158.7		155.0		3.7		—
Short-term investments	1,132.6		1,068.4		64.2		—
Other long-term investments(2)	86.9		—		—		86.9
Total investments	$	3,337.1	$	1,359.6	$	1,888.0	$	89.5
Loan participation	28.5		—		—		28.5
Derivative instruments	7.7		6.6		—		1.1
Total assets measured at fair value	$	3,373.3	$	1,366.2	$	1,888.0	$	119.1
Liabilities measured at fair value
Contingent consideration liabilities	$	0.3	$	—	$	—	$	0.3
Derivative instruments	3.6		0.1		—		3.5
Total liabilities measured at fair value	$	3.9	$	0.1	$	—	$	3.8

(1)Sirius Group engaged in short selling of certain equity securities for which settlement was pending as of September 30, 2020.

(2)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

	December 31, 2019
(Millions)	Fair value		Level 1 inputs		Level 2 inputs		Level 3 inputs
Assets measured at fair value
Fixed maturity investments:
U.S. Government and government agency	$	110.5	$	109.1	$	1.4	$	—
Corporate debt securities	474.1		—		474.1		—
Asset-backed securities	486.8		—		486.8		—
Residential mortgage-backed securities	438.9		—		438.9		—
Commercial mortgage-backed securities	89.0		—		89.0		—
Non-U.S. government and government agency	63.0		31.7		31.3		—
Preferred stocks	17.0		—		—		17.0
U.S. States, municipalities, and political subdivision	1.7		—		1.7		—
Total fixed maturity investments	1,681.0		140.8		1,523.2		17.0
Equity securities:
Fixed income mutual funds	175.3		175.3		—		—
Common stocks	228.1		228.1		—		—
Other equity securities	1.8		—		1.8		—
Total equity securities	405.2		403.4		1.8		—
Short-term investments	1,085.2		1,073.7		11.5		—
Other long-term investments(1)	77.8		—		—		77.8
Total investments	$	3,249.2	$	1,617.9	$	1,536.5	$	94.8
Loan participation	20.0		—		—		20.0
Derivative instruments	11.4		1.3		—		10.1
Total assets measured at fair value	$	3,280.6	$	1,619.2	$	1,536.5	$	124.9
Liabilities measured at fair value
Contingent consideration liabilities	$	28.2	$	—	$	—	$	28.2
Derivative instruments	9.5		0.2		—		9.3
Total liabilities measured at fair value	$	37.7	$	0.2	$	—	$	37.5

(1)Excludes fair value of $269.0 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

Rollforward of Level 3 fair value measurements

The following tables present changes in Level 3 for financial instruments measured at fair value for the three months ended September 30, 2020 and September 30, 2019:

	For the three months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2020	$	2.6	$	78.2	$	27.3	$	1.5	$	(22.9)
Total realized and unrealized gains (losses)	—		8.2		—		(1.7)		(0.3)
Foreign currency gains through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		—		2.5		—		—
Sales/Settlements(2)	—		—		(1.3)		(2.2)		22.9
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $4.5 payment of contingent consideration for the 2017 purchase of Armada.

	For the three months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of June 30, 2019	$	—	$	88.0	$	—	$	(3.6)	$	(30.8)
Total realized and unrealized (losses)	—		(0.3)		—		(2.0)		(2.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.0)		—		—		—
Purchases	17.0		—		—		—		—
Sales/Settlements(2)	—		(6.0)		—		3.4		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

The following tables present changes in Level 3 for financial instruments measured at fair value for the nine months ended September 30, 2020 and September 30, 2019:

	For the nine months ended September 30, 2020
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2020	$	17.0	$	77.8	$	20.0	$	0.8	$	(28.2)
Total realized and unrealized gains (losses)	2.6		3.1		—		(20.7)		(0.5)
Foreign currency (losses) through Other Comprehensive Income	—		0.5		—		—		—
Purchases	—		5.5		9.9		—		—
Sales/Settlements(2)	(17.0)		—		(1.4)		17.5		28.4
Balance as of September 30, 2020	$	2.6	$	86.9	$	28.5	$	(2.4)	$	(0.3)

(1)Excludes fair value of $301.1 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $18.4 payment of contingent consideration for 2017 purchase of IMG and $10.0 payment of contingent consideration for the 2017 purchase of Armada.

	For the nine months ended September 30, 2019
(Millions)	Fixed Maturities		Other long-term investments(1)		Loan Participation		Derivative instruments assets & (liabilities)		Contingent consideration (liabilities)
Balance as of January 1, 2019	$	5.4	$	63.6	$	—	$	(0.5)	$	(28.8)
Total realized and unrealized gains (losses)	—		10.6		—		(7.7)		(4.1)
Foreign currency (losses) through Other Comprehensive Income	—		(1.5)		—		—		—
Purchases	17.0		15.8		—		—		—
Sales/Settlements(2)	(5.4)		(7.8)		—		6.0		6.9
Balance as of September 30, 2019	$	17.0	$	80.7	$	—	$	(2.2)	$	(26.0)

(1)Excludes fair value of $287.7 associated with hedge funds and private equity funds which fair value is measured using NAV practical expedient.

(2)Includes $6.9 payment of contingent consideration for 2017 purchase of IMG.

Schedule of significant unobservable inputs used for recurring fair value measurements for Level 3 instruments

The table below presents information about the significant unobservable inputs used for recurring fair value measurements for certain Level 3 instruments as of September 30, 2020 and December 31, 2019, and includes only those instruments for which information about the inputs is reasonably available to Sirius Group, such as data from independent third-party valuation service providers and from internal valuation models.

(Millions, except share prices)	September 30, 2020
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities (1)	Purchase price of recent transaction	$	32.5	Purchase price	40.63
Preferred stock (1)	Purchase price of recent transaction	$	27.9	Purchase price	7.74
Loan participation (1)	Purchase price of recent transaction	$	18.5	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private equity securities (1)	Multiple of GAAP book value	$	13.3	Book value multiple	Range - 0.73x-0.91x Median - 0.82x
Loan participation (1)	Purchase price of recent transaction	$	10.0	Comparable yields	Range - 4.46% - 7.82% Median - 5.74%
Private debt instrument (1)	Discounted cash flow	$	6.2	Discount yield	Range - 11.87% - 12.32% Median - 12.08%
Private equity securities (1)	Purchase price of recent transaction	$	4.7	Purchase price	7.74
Private convertible debt instrument (1)	Unit price of recent transaction	$	2.0	Purchase price	7.74
Preferred stock (1)	Purchase price of recent transaction	$	1.9	Purchase price	$	1.9
Preferred stock (1)	Purchase price of recent transaction	$	0.7	Purchase price	$	0.7
Equity warrants	Option pricing model	$	0.5	Strike price	$	0.2
Currency swaps (2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Currency forwards(2)	Third party appraisal	$	0.3	Broker quote	$	0.3
Private equity securities (1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Contingent consideration	External valuation model	$	(0.3)	Discounted future payment	$	(0.3)
Weather derivatives (2)	Third party appraisal	$	(3.5)	Broker quote	$	(3.5)

(1)As of September 30, 2020, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

(Millions, except share prices)	December 31, 2019
Description	Valuation Technique(s)	Fair value		Unobservable input
Private equity securities(1)	Share price of recent transaction	$	32.5	Purchase share price	$	40.6
Loan participation(1)	Purchase price of recent transaction	$	20.0	Purchase price	20.0
Preferred stock(1)	Share price of recent transaction	$	17.5	Purchase price	$	7.74
Private equity securities(1)	Multiple of GAAP book value	$	14.2	Book value multiple	0.9
Preferred stock(1)	Purchase price of recent transaction	$	12.2	Purchase price	$	12.2
Private debt instrument(1)	Purchase price of recent transaction	$	7.2	Purchase price	$	9.0
Weather derivatives(2)	Third party appraisal	$	7.0	Broker quote	$	7.0
Private equity securities(1)	Purchase price of recent transaction	$	5.1	Purchase price	$	7.74
Preferred stock(1)	Purchase price of recent transaction	$	4.8	Purchase price	$	4.80
Currency forwards(2)	Third party appraisal	$	2.7	Broker quote	$	2.7
Private equity securities(1)	Purchase price of recent transaction	$	1.0	Purchase price	$	10.0
Equity warrants(2)	Option pricing model	$	0.4	Strike price	$	0.2
Private equity securities(1)	Purchase price of recent transaction	$	0.3	Purchase price	$	0.3
Currency swaps(2)	Third party appraisal	$	(3.6)	Broker quote	$	(3.6)
Currency forwards(2)	Third party appraisal	$	(5.7)	Broker quote	$	(5.7)
Contingent consideration	External valuation model	$	(28.2)	Discounted future payments	$	(28.2)

(1)As of December 31, 2019, each asset type consists of one security.

(2)See Note 12 for discussion of derivative instruments.

Schedule of financial instruments disclosed, but not carried at fair value

The following table includes financial instruments for which the carrying value differs from the estimated fair values at September 30, 2020 and December 31, 2019:

	September 30, 2020				December 31, 2019
(Millions)	Fair Value(1)		Carrying Value		Fair Value(1)		Carrying Value
Liabilities, Mezzanine equity, and Non-controlling interest:
2017 SEK Subordinated Notes	$	298.8	$	301.3	$	294.5	$	291.2
2016 SIG Senior Notes	$	394.7	$	394.5	$	394.5	$	394.0
Series B preference shares	$	244.5	$	197.5	$	186.4	$	223.0

(1)Fair value estimated by internal pricing and considered a Level 3 measurement.

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Debt and standby letters of credit facilities (Tables)

9 Months Ended

Sep. 30, 2020

Debt Disclosure [Abstract]

Schedule of debt outstanding

Sirius Group's debt outstanding as of September 30, 2020 and December 31, 2019 consisted of the following:

(Millions)	September 30, 2020		Effective Rate(1)		December 31, 2019		Effective Rate(1)
2017 SEK Subordinated Notes, at face value	$	305.0	4.3	%	$	295.0	4.0	%
Unamortized issuance costs	(3.7)				(3.8)
2017 SEK Subordinated Notes, carrying value	301.3				291.2
2016 SIG Senior Notes, at face value	400.0		4.7	%	400.0		4.7	%
Unamortized discount	(2.1)				(2.3)
Unamortized issuance costs	(3.4)				(3.7)
2016 SIG Senior Notes, carrying value	394.5				394.0
Total debt	$	695.8			$	685.2

(1) Effective rate considers the effect of the debt issuance costs.

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Derivatives (Tables)

9 Months Ended

Sep. 30, 2020

Derivative Instruments and Hedging Activities Disclosure [Abstract]

Schedule of classification and amount of fair value of derivatives not designated as hedging instruments within consolidated balance sheets

The following tables summarize information on the classification and amount of the fair value of derivatives not designated as hedging instruments within the Company's Consolidated Balance Sheets as at September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020						December 31, 2019
Derivatives not designated as hedging instruments	Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)		Notional Value		Asset derivative at fair value(1)		Liability derivative at fair value(2)
Interest rate cap	$	250.0	$	—	$	—	$	250.0	$	—	$	—
Foreign currency swaps	$	40.0	$	0.3	$	—	$	90.0	$	—	$	3.6
Foreign currency forwards	$	225.2	$	0.3	$	—	$	(30.0)	$	2.7	$	5.7
Weather derivatives	$	53.6	$	—	$	3.5	$	110.7	$	7.0	$	—
Equity futures contracts	$	(1.0)	$	—	$	—	$	34.5	$	—	$	—
Foreign currency futures contracts	$	22.3	$	—	$	—	$	—	$	—	$	—
Equity call options	$	34.6	$	2.5	$	—	$	—	$	—	$	—
Equity put options	$	77.3	$	1.9	$	0.1	$	31.0	$	1.3	$	0.2
Foreign currency call options	$	50.6	$	2.2	$	—	$	—	$	—	$	—
Equity warrants	$	0.5	$	0.5	$	—	$	0.4	$	0.4	$	—

(1)Asset derivatives are classified within Other assets within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

(2)Liability derivatives are classified within Other liabilities within the Company's Consolidated Balance Sheets at September 30, 2020 and December 31, 2019.

Schedule of classification and net impact on earnings, recognized in Consolidated Statements of Income relating to derivatives

The following table summarizes information on the classification and net impact on earnings, recognized in the Company's Consolidated Statements of (Loss) Income relating to derivatives during the three and nine months ended September 30, 2020 and 2019:

(Millions)		For the three months ended September 30,				For the nine months ended September 30,
Derivatives not designated as hedging instruments	Classification of gains (losses) recognized in earnings	2020		2019		2020		2019
Interest rate cap	Other revenues	$	—	$	—	$	—	$	(0.2)
Foreign currency swaps	Net foreign exchange (losses) gains	$	(0.9)	$	3.7	$	1.8	$	6.1
Foreign currency forwards	Net foreign exchange (losses) gains	$	(0.4)	$	(7.8)	$	(0.9)	$	(10.8)
Weather derivatives	Other revenues	$	(0.4)	$	1.9	$	(21.8)	$	(3.6)
Equity futures contracts	Net realized investment (losses) gains	$	(0.2)	$	0.1	$	2.4	$	(0.7)
Equity futures contracts	Net unrealized investment gains (losses)	$	(0.1)	$	(0.5)	$	0.4	$	(0.6)
Foreign currency futures contracts	Net foreign exchange (losses) gains	$	0.8	$	—	$	0.1	$	—
Equity put options	Net realized investment (losses) gains	$	1.9	$	(0.8)	$	7.8	$	(0.8)
Equity put options	Net unrealized investment gains (losses)	$	(0.6)	$	0.7	$	0.8	$	0.2
Foreign currency call options	Net foreign exchange (losses) gains	$	1.0	$	—	$	0.8	$	—
Equity warrants	Net unrealized investment gains (losses)	$	(0.1)	$	0.3	$	0.1	$	0.7

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Share-based compensation (Tables)

9 Months Ended

Sep. 30, 2020

Share-based Payment Arrangement [Abstract]

Summary of unrecognized compensation cost associated with unvested awards and weighted average period over which it is expected to be recognized

The following tables present unrecognized compensation cost associated with unvested awards and weighted average period over which it is expected to be recognized:

(Millions)	September 30, 2020
	RSUs		Stock Options
Unrecognized compensation cost related to unvested awards	$	6.4	$	1.3
Weighted average recognition period (years)	1.3 years		1.5 years

Summary of outstanding share-settled awards

The following table summarizes outstanding and changes in share-settled awards for the three and nine months ended September 30, 2020:

	Number of Shares
Three months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,274,752	1,374,945
Granted	—	—
Vested	—	—
Forfeited	1,060	—
Unvested, end of period	1,273,692	1,374,945

	Number of Shares
Nine months ended September 30, 2020	RSUs	Stock Options
Unvested, beginning of period	1,353,852	1,374,945
Granted	—	—
Vested	—	—
Forfeited	80,160	—
Unvested, end of period	1,273,692	1,374,945

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Common shareholder's equity, mezzanine equity, and non-controlling interests (Tables)

9 Months Ended

Sep. 30, 2020

Equity [Abstract]

Schedule of changes in the company's issued and outstanding common shares

The following table presents changes in the Company's issued and outstanding Common shares for the three and nine months ended September 30, 2020 and 2019, respectively:

	Three months ended September 30,		Nine months ended September 30,
	2020	2019	2020	2019
Common shares:
Shares issued and outstanding, beginning of period	115,299,341	115,296,918	115,299,341	115,151,251
Issuance of shares to directors and employees	—	2,424	—	148,091
Shares issued and outstanding, end of period	115,299,341	115,299,342	115,299,341	115,299,342

Schedule of change in non-controlling interest

The following tables show the change in non-controlling interest for the three and nine months ended September 30, 2020 and 2019:

(Millions)	For the three months ended September 30, 2020		For the three months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.5	$	3.0
Net income attributable to non-controlling interests	0.2		0.4
Dividends paid	(1.0)		—
Other, net	0.1		—
Non-controlling interests, end of the period	$	1.8	$	3.4

(Millions)	For the nine months ended September 30, 2020		For the nine months ended September 30, 2019
Non-controlling interests, beginning of the period	$	2.4	$	1.7
Net income attributable to non-controlling interests	0.2		1.6
Dividends paid	(1.0)		—
Other, net	0.2		0.1
Non-controlling interests, end of the period	$	1.8	$	3.4

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Earnings per share (Tables)

9 Months Ended

Sep. 30, 2020

Earnings Per Share [Abstract]

Schedule of computation of basic and diluted earnings per common share

The following table sets forth the computation of basic and diluted earnings per common share for the three and nine months ended September 30, 2020 and 2019:

	For the three months ended September 30,				For the nine months ended September 30,
(Millions, except share and per share information)	2020		2019		2020		2019
Basic earnings per share
Numerator:
Net income	$	(104.0)	$	(7.6)	$	(232.5)	$	104.7
Less: Income attributable to non-controlling interests	(0.2)		(0.4)		(0.2)		(1.6)
Less: Change in carrying value of Series B preference shares	8.7		5.3		25.5		(3.9)
Net income available for dividends out of undistributed earnings	$	(95.5)	$	(2.7)	$	(207.2)	$	99.2
Less: Earnings attributable to Series B preference shares	—		—		—		(9.3)
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Basic earnings per share	$	(0.83)	$	(0.02)	$	(1.80)	$	0.78
Diluted earnings per share
Numerator:
Net income available to Sirius Group common shareholders	$	(95.5)	$	(2.7)	$	(207.2)	$	89.9
Add: Change in carrying value of Series B preference shares	—		(5.3)		(25.5)		—
Net income available to Sirius Group common shareholders on a diluted basis	$	(95.5)	$	(8.0)	$	(232.7)	$	89.9
Denominator:
Weighted average shares outstanding for basic earnings per share	115,297,945		115,251,853		115,279,197		115,225,942
Add: Series B preference shares	—		11,901,670		11,901,670		—
Add: Unvested performance share units and restricted share units	—		—		—		393,280
Weighted average shares outstanding for diluted earnings per share(1)	115,297,945		127,153,523		127,180,867		115,619,222
Diluted earnings per share	$	(0.83)	$	(0.06)	$	(1.83)	$	0.78

(1)For the three months ended September 30, 2020, there were a total of 26,057,275 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the three months ended September 30, 2019, there were 19,537,270 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2020, there were a total of 14,155,605 potentially dilutive securities excluded from the calculation of Diluted earnings per share. For the nine months ended September 30, 2019, there were 31,045,660 potentially dilutive securities excluded from the calculation of Diluted earnings per share.

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Investments in unconsolidated entities (Tables)

9 Months Ended

Sep. 30, 2020

Investments in unconsolidated entities

Schedule of components of other long-term investments

The following table presents the components of Other long-term investments as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Equity method eligible unconsolidated entities, at fair value	$	166.8	$	151.9
Other unconsolidated investments, at fair value(1)	221.2		194.9
Total Other long-term investments(2)	$	388.0	$	346.8

(1)Includes Other long-term investments that are not equity method eligible.

(2)There were no investments accounted for using the equity method as of September 30, 2020 and December 31, 2019.

Schedule of investments in equity method eligible unconsolidated entities

The following table presents Sirius Group's investments in equity method eligible unconsolidated entities as of September 30, 2020 and December 31, 2019:

	Ownership interest as of
Investee	September 30, 2020		December 31, 2019		Instrument Held
BE Reinsurance Limited	24.9	%	24.9	%	Common shares
BioVentures Investors (Offshore) IV LP	73.0	%	73.0	%	Units
Camden Partners Strategic Fund V (Cayman), LP	39.4	%	39.4	%	Units
Diamond LS I LP	15.6	%	16.0	%	Units
Gateway Fund LP	22.9	%	15.0	%	Units
Monarch	12.8	%	12.8	%	Units
New Energy Capital Infrastructure Credit Fund LP	29.8	%	30.5	%	Units
New Energy Capital Infrastructure Offshore Credit Fund LP	29.8	%	30.5	%	Units
Pie Preferred Stock(1)	30.1	%	30.1	%	Preferred shares
Pie Series B Preferred Stock(1)	23.4	%	22.4	%	Preferred shares
Quintana Energy Partners	21.8	%	21.8	%	Units
Tuckerman Capital V LP	48.3	%	48.3	%	Units
Tuckerman Capital V Co-Investment I LP	48.3	%	48.1	%	Units

(1)Sirius Group holds investments in several financing instruments of Pie Insurance Holdings, Inc.

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Variable interest entities (Tables)

9 Months Ended

Sep. 30, 2020

Organization, Consolidation and Presentation of Financial Statements [Abstract]

Schedule of assets and liabilities related to the consolidated VIEs

The following table presents Alstead Re's assets and liabilities, as classified in the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(Millions)	September 30, 2020		December 31, 2019
Assets:
Fixed maturity investments	$	3.8	$	3.9
Short-term investments	0.5		0.5
Cash	0.1		0.1
Total investments	4.3		4.5
Insurance and reinsurance premiums receivable	(0.5)		(0.3)
Funds held by ceding companies	2.3		3.4
Deferred acquisition costs	—		0.3
Other assets	—		—
Total assets	$	6.2	$	7.9
Liabilities
Loss and loss adjustment expense reserves	$	0.3	$	0.5
Unearned insurance and reinsurance premiums	—		0.6
Other liabilities	0.1		0.1
Total liabilities	$	0.4	$	1.2

Schedule of total assets of unconsolidated VIEs

The following table presents total assets of unconsolidated VIEs in which Sirius Group holds a variable interest, as well as the maximum exposure to loss associated with these VIEs:

			Maximum Exposure to Loss
(Millions)	Total VIE Assets		On-Balance Sheet		Off-Balance Sheet		Total
September 30, 2020
Other long-term investments(1)	$	254.8	$	117.1	$	7.4	$	124.5
Total at September 30, 2020	$	254.8	$	117.1	$	7.4	$	124.5
December 31, 2019
Other long-term investments(1)	$	257.8	$	102.6	$	16.3	$	118.9
Total at December 31, 2019	$	257.8	$	102.6	$	16.3	$	118.9

(1)Comprised primarily of hedge funds and private equity funds.

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Commitments and contingencies (Tables)

9 Months Ended

Sep. 30, 2020

Commitments and Contingencies Disclosure [Abstract]

Schedule of lease balances within the consolidated balance sheets

The following table presents the lease balances within the Consolidated Balance Sheets as of September 30, 2020 and December 31, 2019:

(millions)	Balance Sheet Classification	September 30, 2020	December 31, 2019
Operating lease right-of-use assets	Other assets	$27.1	$27.4
Current lease liabilities	Other liabilities	$9.2	$8.3
Non-current lease liabilities	Other liabilities	$19.8	$21.0

Schedule of weighted average remaining lease term and weighted average discount rate

The following table presents weighted average remaining lease term and weighted average discount rate as of September 30, 2020:

Weighted average lease term (years) as at September 30, 2020
Leased offices	7 years
Leased equipment	3 years
Weighted average discount rate:
Leased offices	3.3	%
Leased equipment	3.3	%

Schedule of future annual minimum rental payments required under non cancellable leases for office space

The following table presents future annual minimum rental payments required under non-cancellable leases and the present value discount to arrive at total lease liability as of September 30, 2020:

(Millions)	Future Payments
2020	$	2.4
2021	9.6
2022	9.5
2023	5.7
2024	2.3
2025 and after	1.2
Total future annual minimum rental payments as of September 30, 2020	30.7
Less: present value discount	(1.7)
Total lease liability as of September 30, 2020	$	29.0

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Summary of significant accounting policies - Recent adopted changes in accounting principle and Recent accounting pronouncements (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2019	Sep. 30, 2020	Jun. 30, 2020	Jan. 01, 2020	Sep. 30, 2019	Jun. 30, 2019	Dec. 31, 2018
Summary of significant accounting policies
Allowance for credit loss		$ 0.4
Cumulative effect of an accounting change	$ 1,642.8	1,461.0			$ 1,746.0
Accounting Standards Update [Extensible List]	us-gaap:AccountingStandardsUpdate201613Member
Accounting Standards Update 2016-13
Summary of significant accounting policies
Allowance for credit loss				$ 14.9
Retained earnings
Summary of significant accounting policies
Cumulative effect of an accounting change	$ 778.5	$ 564.5	$ 660.0		$ 915.8	$ 918.5	$ 816.6
Cumulative effect, period of adoption | Retained earnings
Summary of significant accounting policies
Cumulative effect of an accounting change	$ (6.8)

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Significant transactions (Details) $ / shares in Units, $ in Millions	3 Months Ended	9 Months Ended
	Sep. 30, 2020 USD ($) $ / shares	Sep. 30, 2020 USD ($) $ / shares	Aug. 06, 2020 contingent_value_right $ / shares shares
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Common shares par value (in dollars per share)	$ 0.01	$ 0.01
Payments for litigation | $		$ 2.2
TPRE shares
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Right to receive in cash (in dollars per share)			$ 0.905
Warrants issued (in shares) | shares			0.190
Value of warrants (in dollars per share)			$ 0.905
Merger agreement
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Right to receive in cash (in dollars per share)			9.50
Other costs | $	$ 10.0	$ 10.0
Merger agreement | TPRE shares
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Common shares par value (in dollars per share)			$ 0.10
Right to receive common stock (in shares) | shares			0.743
Number of CVRs | contingent_value_right			1
Right to receive cash and equity (in dollars per share)			$ 13.73

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Significant transactions - Loss Portfolio Transfer (Details) - USD ($) $ in Millions			9 Months Ended
	Jul. 07, 2020	Jan. 23, 2020	Sep. 30, 2020	Sep. 30, 2019
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposition of business			$ 0.9	$ 0.0
Cash received in loss portfolio transfer agreement		$ 69.7
Cash paid in loss portfolio transfer agreement		$ 0.4
Empire Insurance Company | Runoff & Other
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Percentage of stock disposed of	100.00%
Proceeds from fees received	$ 11.4
Gain (loss) on disposition of business	$ 0.9

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Segment information - Segment results (Details) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020 USD ($)	Sep. 30, 2019 USD ($)	Sep. 30, 2020 USD ($) product segment	Sep. 30, 2019 USD ($)
Segment information
Number of reportable segments | segment			4
Gross written premiums	$ 356.0	$ 413.7	$ 1,496.2	$ 1,523.1
Net written premiums	282.3	322.3	1,218.2	1,208.8
Net earned insurance and reinsurance premiums	372.6	374.2	1,177.1	1,056.8
Loss and allocated LAE	(291.3)	(334.4)	(925.1)	(775.7)
Insurance and reinsurance acquisition expenses	(83.6)	(75.1)	(236.4)	(215.4)
Technical (loss) profit	(2.3)	(35.3)	15.6	65.7
Unallocated LAE	(14.1)	(14.2)	(47.7)	(34.8)
Other underwriting expenses	(41.3)	(35.4)	(115.6)	(106.2)
Underwriting (loss) income	(57.7)	(84.9)	(147.7)	(75.3)
Service fee revenue	16.5	16.4	52.8	58.3
General and administrative expenses, MGU plus Runoff & Other	(34.4)	(28.0)	(90.4)	(80.6)
Underwriting (loss) income, including net service fee income	(53.1)	(84.8)	(134.9)	(66.3)
Net investment income	1.7	22.8	30.0	67.3
Net realized investment gains	(3.8)	15.3	23.6	39.9
Net unrealized investment gains	31.2	53.9	(3.9)	143.4
Net foreign exchange (losses)	(21.3)	4.9	(18.9)	9.4
Other revenue	(0.7)	(0.1)	(22.5)	(7.0)
General and administrative expenses	(22.5)	(11.7)	(50.4)	(31.3)
Intangible asset amortization expenses	(3.9)	(3.9)	(11.8)	(11.8)
Interest expense on debt	(8.1)	(7.7)	(23.8)	(23.3)
Pre-tax income (loss)	$ (80.5)	$ (11.3)	$ (212.6)	$ 120.3
Underwriting Ratios
Loss ratio	82.00%	93.20%	82.60%	76.70%
Acquisition expense ratio	22.40%	20.10%	20.10%	20.40%
Other underwriting expense ratio	11.10%	9.50%	9.80%	10.00%
Combined ratio	115.50%	122.80%	112.50%	107.10%
Goodwill and intangible assets	$ 568.8	$ 584.2	$ 568.8	$ 584.2
Managing general underwriters
Segment information
General and administrative expenses, MGU plus Runoff & Other	(11.9)	(16.3)	(40.0)	(49.3)
Corporate Eliminations
Segment information
Insurance and reinsurance acquisition expenses	9.6	13.8	30.2	36.7
Technical (loss) profit	9.6	13.8	30.2	36.7
Unallocated LAE	(4.7)	(3.5)	(14.8)	(11.1)
Other underwriting expenses	(4.7)	(3.7)	(14.4)	(11.2)
Underwriting (loss) income	0.2	6.6	1.0	14.4
Service fee revenue	(10.7)	(14.6)	(33.4)	(39.3)
Corporate Eliminations | Managing general underwriters
Segment information
Unallocated LAE	5.8	4.3	18.0	13.7
Other underwriting expenses	4.7	3.7	14.4	11.2
Global Reinsurance
Segment information
Net written premiums	192.2	202.6	758.1	805.2
Global Reinsurance | Reportable segments
Segment information
Gross written premiums	248.2	256.3	927.0	1,008.4
Net written premiums	192.2	202.6	758.1	805.2
Net earned insurance and reinsurance premiums	243.5	249.5	719.4	705.7
Loss and allocated LAE	(194.5)	(261.7)	(600.2)	(558.0)
Insurance and reinsurance acquisition expenses	(51.8)	(54.3)	(156.4)	(149.9)
Technical (loss) profit	(2.8)	(66.5)	(37.2)	(2.2)
Unallocated LAE	(7.7)	(8.4)	(17.9)	(17.1)
Other underwriting expenses	(25.3)	(20.8)	(67.1)	(64.0)
Underwriting (loss) income	(35.8)	(95.7)	(122.2)	(83.3)
Underwriting (loss) income, including net service fee income	$ (35.8)	$ (95.7)	$ (122.2)	$ (83.3)
Underwriting Ratios
Loss ratio	83.00%	108.30%	85.90%	81.50%
Acquisition expense ratio	21.30%	21.80%	21.70%	21.20%
Other underwriting expense ratio	10.40%	8.30%	9.30%	9.10%
Combined ratio	114.70%	138.40%	116.90%	111.80%
Global A&H
Segment information
Net written premiums	$ 72.2	$ 104.6	$ 334.9	$ 360.1
Global A&H | Reportable segments
Segment information
Gross written premiums	88.8	137.4	434.6	459.5
Net written premiums	72.2	104.6	334.9	360.1
Net earned insurance and reinsurance premiums	114.3	115.1	345.4	330.0
Loss and allocated LAE	(84.6)	(63.6)	(234.5)	(198.6)
Insurance and reinsurance acquisition expenses	(36.6)	(32.5)	(98.9)	(95.1)
Technical (loss) profit	(6.9)	19.0	12.0	36.3
Unallocated LAE	(0.5)	(2.0)	(2.8)	(5.5)
Other underwriting expenses	(5.7)	(6.8)	(18.0)	(18.8)
Underwriting (loss) income	(13.1)	10.2	(8.8)	12.0
Service fee revenue	26.3	31.0	85.3	97.6
Underwriting (loss) income, including net service fee income	$ (8.3)	$ 18.1	$ 7.9	$ 38.4
Underwriting Ratios
Loss ratio	74.50%	57.00%	68.70%	61.80%
Acquisition expense ratio	32.00%	28.20%	28.60%	28.80%
Other underwriting expense ratio	5.00%	5.90%	5.20%	5.70%
Combined ratio	111.50%	91.10%	102.50%	96.30%
Goodwill and intangible assets	$ 560.7	$ 576.1	$ 560.7	$ 576.1
Global A&H | Reportable segments | Managing general underwriters
Segment information
Unallocated LAE	(5.8)	(4.3)	(18.0)	(13.7)
Other underwriting expenses	(4.7)	(3.7)	(14.4)	(11.2)
General and administrative expenses, MGU plus Runoff & Other	(11.0)	(15.1)	$ (36.2)	(46.3)
U.S. Specialty
Segment information
Number of core products | product			4
Net written premiums	20.5	14.3	$ 59.5	42.0
U.S. Specialty | Reportable segments
Segment information
Gross written premiums	22.6	17.9	68.9	50.5
Net written premiums	20.5	14.3	59.5	42.0
Net earned insurance and reinsurance premiums	17.2	9.1	45.2	19.9
Loss and allocated LAE	(11.1)	(8.2)	(29.2)	(14.7)
Insurance and reinsurance acquisition expenses	(4.0)	(2.0)	(10.4)	(4.5)
Technical (loss) profit	2.1	(1.1)	5.6	0.7
Unallocated LAE	(0.2)	(0.1)	(0.4)	(0.2)
Other underwriting expenses	(4.3)	(2.7)	(12.4)	(7.6)
Underwriting (loss) income	(2.4)	(3.9)	(7.2)	(7.1)
Underwriting (loss) income, including net service fee income	$ (2.4)	$ (3.9)	$ (7.2)	$ (7.1)
Underwriting Ratios
Loss ratio	65.70%	91.20%	65.50%	74.90%
Acquisition expense ratio	23.30%	22.00%	23.00%	22.60%
Other underwriting expense ratio	25.00%	29.70%	27.40%	38.20%
Combined ratio	114.00%	142.90%	115.90%	135.70%
U.S. Specialty | Reportable segments | Minimum
Segment information
Pre-agreed domestic and export sales of goods and services coverage period			60 days
U.S. Specialty | Reportable segments | Maximum
Segment information
Pre-agreed domestic and export sales of goods and services coverage period			120 days
Runoff & Other
Segment information
Net written premiums	$ (2.6)	$ 0.8	$ 65.7	$ 1.5
Runoff & Other | Reportable segments
Segment information
Gross written premiums	(3.6)	2.1	65.7	4.7
Net written premiums	(2.6)	0.8	65.7	1.5
Net earned insurance and reinsurance premiums	(2.4)	0.5	67.1	1.2
Loss and allocated LAE	(1.1)	(0.9)	(61.2)	(4.4)
Insurance and reinsurance acquisition expenses	(0.8)	(0.1)	(0.9)	(2.6)
Technical (loss) profit	(4.3)	(0.5)	5.0	(5.8)
Unallocated LAE	(1.0)	(0.2)	(11.8)	(0.9)
Other underwriting expenses	(1.3)	(1.4)	(3.7)	(4.6)
Underwriting (loss) income	(6.6)	(2.1)	(10.5)	(11.3)
Service fee revenue	0.9		0.9
Underwriting (loss) income, including net service fee income	(6.6)	(3.3)	(13.4)	(14.3)
Underwriting Ratios
Goodwill and intangible assets	8.1	8.1	8.1	8.1
Runoff & Other | Reportable segments | Managing general underwriters
Segment information
General and administrative expenses, MGU plus Runoff & Other	$ (0.9)	$ (1.2)	$ (3.8)	$ (3.0)

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Segment information - Net premiums written by client location and underwriting location by reportable segment (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	$ 282.3	$ 322.3	$ 1,218.2	$ 1,208.8
Client location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	165.3	215.4	714.5	726.3
Client location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	56.3	35.4	284.6	226.7
Client location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	24.6	28.3	80.7	81.0
Client location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	36.1	43.2	138.4	174.8
Underwriting location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	103.7	57.8	476.1	194.8
Underwriting location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	128.3	164.3	526.1	600.3
Underwriting location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	39.4	90.7	170.7	367.8
Underwriting location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	10.9	9.5	45.3	45.9
Global Reinsurance
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	192.2	202.6	758.1	805.2
Global Reinsurance | Client location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	86.7	112.8	297.9	382.1
Global Reinsurance | Client location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	49.3	29.7	264.8	207.7
Global Reinsurance | Client location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	25.9	24.5	74.2	70.2
Global Reinsurance | Client location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	30.3	35.6	121.2	145.2
Global Reinsurance | Underwriting location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	53.8	20.2	162.5	57.8
Global Reinsurance | Underwriting location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	84.9	81.9	376.3	368.0
Global Reinsurance | Underwriting location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	42.8	91.3	174.6	334.4
Global Reinsurance | Underwriting location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	10.7	9.2	44.7	45.0
Global A&H
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	72.2	104.6	334.9	360.1
Global A&H | Client location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	57.3	87.6	288.7	301.2
Global A&H | Client location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	7.0	5.8	19.4	18.9
Global A&H | Client location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	2.3	3.7	10.1	10.7
Global A&H | Client location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	5.6	7.5	16.7	29.3
Global A&H | Underwriting location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	28.6	36.9	185.7	136.0
Global A&H | Underwriting location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	43.4	68.1	149.4	190.1
Global A&H | Underwriting location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.2	(0.6)	(0.3)	33.4
Global A&H | Underwriting location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.2	0.1	0.6
U.S. Specialty
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	20.5	14.3	59.5	42.0
U.S. Specialty | Client location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	20.5	14.3	59.5	42.0
U.S. Specialty | Client location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.0	0.0
U.S. Specialty | Client location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.0	0.0
U.S. Specialty | Client location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.0	0.0
U.S. Specialty | Underwriting location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	20.5	0.0	59.5	0.0
U.S. Specialty | Underwriting location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	14.3	0.0	42.0
U.S. Specialty | Underwriting location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.0	0.0
U.S. Specialty | Underwriting location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.0	0.0
Runoff & Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	(2.6)	0.8	65.7	1.5
Runoff & Other | Client location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.8	0.7	68.4	1.0
Runoff & Other | Client location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	(0.1)	0.4	0.1
Runoff & Other | Client location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	(3.6)	0.1	(3.6)	0.1
Runoff & Other | Client location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.2	0.1	0.5	0.3
Runoff & Other | Underwriting location: United States
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.8	0.7	68.4	1.0
Runoff & Other | Underwriting location: Europe
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	0.0	0.0	0.4	0.2
Runoff & Other | Underwriting location: Canada, the Caribbean, Bermuda and Latin America
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	(3.6)	0.0	(3.6)	0.0
Runoff & Other | Underwriting location: Asia and Other
Net premiums written by client location and underwriting location by reportable segment
Net written premiums	$ 0.2	$ 0.1	$ 0.5	$ 0.3

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Reserves for unpaid losses and loss adjustment expenses (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Summary of the loss and LAE reserve activities
Gross beginning balance	$ 2,515.1	$ 2,023.3	$ 2,331.5	$ 2,016.7
Less beginning reinsurance recoverable on unpaid losses	(442.2)	(357.4)	(410.3)	(350.2)
Net loss and LAE reserve balance	2,072.9	1,665.9	1,921.2	1,666.5
Losses and LAE incurred relating to:
Current year losses	305.5	342.2	967.5	723.6
Prior years losses	(0.1)	6.4	5.3	86.9
Total net incurred losses and LAE	305.4	348.6	972.8	810.5
Foreign currency translation adjustment to net loss and LAE reserves	20.8	(15.3)	12.2	(15.3)
Accretion of fair value adjustment to net loss and LAE reserves	0.1	0.0	0.1	0.1
Loss and LAE paid relating to:
Current year losses	81.6	97.7	149.2	254.8
Prior years losses	127.2	108.0	566.7	413.5
Total loss and LAE payments	208.8	205.7	715.9	668.3
Net ending balance	2,190.4	1,793.5	2,190.4	1,793.5
Plus ending reinsurance recoverable on unpaid losses	482.5	392.9	482.5	392.9
Gross ending balance	$ 2,672.9	$ 2,186.4	$ 2,672.9	$ 2,186.4

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Reserves for unpaid losses and loss adjustment expenses - By segment (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Reserves for unpaid losses and loss adjustment expenses
Prior years losses	$ (0.1)	$ 6.4	$ 5.3	$ 86.9
Natural catastrophes
Reserves for unpaid losses and loss adjustment expenses
Prior years losses			22.5
Other property
Reserves for unpaid losses and loss adjustment expenses
Prior years losses			21.6
U S Specialty
Reserves for unpaid losses and loss adjustment expenses
Prior years losses	0.8		(2.0)
Runoff & Other
Reserves for unpaid losses and loss adjustment expenses
Prior years losses	0.4			5.4
Global Reinsurance
Reserves for unpaid losses and loss adjustment expenses
Prior years losses	$ 1.3	10.9	14.9	$ 82.7
Global A&H
Reserves for unpaid losses and loss adjustment expenses
Prior years losses		$ 5.8	(7.6)
Casualty Reinsurance
Reserves for unpaid losses and loss adjustment expenses
Prior years losses			9.2
Aviation and Space
Reserves for unpaid losses and loss adjustment expenses
Prior years losses			$ 10.1

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Third party reinsurance (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Insurance [Abstract]
Reinsurance recoverable on paid losses	$ 70.4	$ 73.9
Reinsurance recoverable on unpaid losses	$ 482.5	$ 410.3

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Allowance for expected credit losses (Details) $ in Millions	Sep. 30, 2020 USD ($)
Ceded Credit Risk [Line Items]
Premiums receivable & Funds held by ceding companies	$ 1,033.1
Reinsurance recoverable on unpaid and paid loss	552.9
MGU Trade receivables	17.2
Total as of June 30, 2020	1,603.2
Premiums receivable & Funds held by ceding companies, allowance for credit losses	10.6
Reinsurance recoverable on unpaid and paid loss, allowance for credit losses	3.9
MGU trade receivable, allowance for credit losses	0.4
Total allowance for credit losses	$ 14.9
Standard & Poor's, A- Rating
Ceded Credit Risk [Line Items]
Percent of the total reinsurance recoverables rated by either A.M. Best or S&P	0.63
AM Best, A- Rating
Ceded Credit Risk [Line Items]
Percent of the total reinsurance recoverables rated by either A.M. Best or S&P	0.67

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Investment securities - Net investment income (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Net Investment Income
Total investment income	$ 5.5	$ 24.8	$ 39.5	$ 76.8
Investment expenses	(3.8)	(2.0)	(9.5)	(9.5)
Net investment income	1.7	22.8	30.0	67.3
Interest on funds held	(8.1)	0.0	(7.5)	0.6
Fixed maturity investments
Net Investment Income
Total investment income	10.1	12.8	31.5	40.0
Short-term investments
Net Investment Income
Total investment income	0.6	4.1	5.2	12.0
Equity securities
Net Investment Income
Total investment income	0.8	2.7	5.5	12.5
Other Long-term Investments
Net Investment Income
Total investment income	$ (6.0)	$ 5.2	$ (2.7)	$ 12.3

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Investment securities - Net realized and unrealized investment gains (losses) (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Net realized and unrealized investment gains (losses)
Gross realized gains	$ 41.3	$ 22.1	$ 140.7	$ 63.1
Gross realized (losses)	(45.1)	(6.8)	(117.1)	(23.2)
Net realized (losses) gains on investments	(3.8)	15.3	23.6	39.9
Net unrealized investment gains (losses)	31.2	53.9	(3.9)	143.4
Net realized and unrealized gains (losses) on investments	27.4	69.2	19.7	183.3
Realized gains due to foreign currency	(11.2)	14.0	5.4	34.5
Unrealized (losses) gains due to foreign currency	(16.7)	33.9	(29.8)	51.7
Total unrealized investment gains (losses) – Level 3 investments	8.2	(0.3)	3.4	10.1
Fixed maturity investments
Net realized and unrealized investment gains (losses)
Net realized (losses) gains on investments	(0.4)	7.5	17.3	22.4
Net unrealized investment gains (losses)	(1.0)	31.4	2.2	72.1
Total unrealized investment gains (losses) – Level 3 investments	0.0	0.0	0.3	0.0
Equity securities
Net realized and unrealized investment gains (losses)
Net realized (losses) gains on investments	1.0	1.7	(5.0)	(0.1)
Net unrealized investment gains (losses)	18.5	12.0	(33.7)	50.4
Short-term investments
Net realized and unrealized investment gains (losses)
Net realized (losses) gains on investments	(6.2)	6.5	(2.4)	9.7
Net unrealized investment gains (losses)	(3.1)	4.6	(3.2)	6.4
Derivative instruments
Net realized and unrealized investment gains (losses)
Net realized (losses) gains on investments	1.8	(0.7)	10.3	(1.5)
Net unrealized investment gains (losses)	(0.8)	0.9	1.4	0.2
Other Long-term Investments
Net realized and unrealized investment gains (losses)
Net realized (losses) gains on investments	0.0	0.3	3.4	9.4
Net unrealized investment gains (losses)	17.6	5.0	29.4	14.3
Total unrealized investment gains (losses) – Level 3 investments	$ 8.2	$ (0.3)	$ 3.1	$ 10.1

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Investment securities - Fixed maturity investments (Details) - USD ($) $ in Millions	9 Months Ended
	Sep. 30, 2020	Dec. 31, 2019
Fixed maturity investments
Cost or amortized cost	$ 1,932.7	$ 1,656.6
Gross unrealized gains	48.1	18.7
Gross unrealized (losses)	(16.0)	(8.2)
Net foreign currency gains (losses)	(5.9)	13.9
Fair value	$ 1,958.9	1,681.0
Weighted average duration of fixed income portfolio including short-term investments	1 year 1 month 6 days
Weighted average duration of fixed income portfolio excluding short-term investments	1 year 7 months 6 days
Cost or amortized cost
Due in one year or less	$ 203.2	85.0
Due after one year through five years	406.7	479.1
Due after five years through ten years	41.0	46.3
Due after ten years	12.3	25.1
Fair value
Due in one year or less	212.2	88.4
Due after one year through five years	404.4	490.3
Due after five years through ten years	41.7	46.0
Due after ten years	12.4	24.6
Fixed maturity investments
Fixed maturity investments
Fair value	1,958.9	1,681.0
Fixed maturity investments | AAA
Fixed maturity investments
Fair value	807.8	559.8
Fixed maturity investments | AA
Fixed maturity investments
Fair value	734.4	724.3
Fixed maturity investments | A
Fixed maturity investments
Fair value	213.7	219.0
Fixed maturity investments | BBB
Fixed maturity investments
Fair value	99.2	95.8
Fixed maturity investments | Other
Fixed maturity investments
Fair value	103.8	82.1
Corporate debt securities
Fixed maturity investments
Cost or amortized cost	471.4	458.6
Gross unrealized gains	10.0	5.2
Gross unrealized (losses)	(0.8)	(1.2)
Net foreign currency gains (losses)	1.3	11.5
Fair value	481.9	474.1
Asset-backed securities
Fixed maturity investments
Cost or amortized cost	740.0	489.4
Gross unrealized gains	8.4	1.4
Gross unrealized (losses)	(12.4)	(3.9)
Net foreign currency gains (losses)	(4.4)	(0.1)
Fair value	731.6	486.8
Residential mortgage-backed securities
Fixed maturity investments
Cost or amortized cost	393.8	426.2
Gross unrealized gains	22.2	10.5
Gross unrealized (losses)	(0.9)	(1.4)
Net foreign currency gains (losses)	1.4	3.6
Fair value	416.5	438.9
U.S. Government and government agency
Fixed maturity investments
Cost or amortized cost	119.2	111.5
Gross unrealized gains	0.8	0.7
Gross unrealized (losses)	0.0	(0.4)
Net foreign currency gains (losses)	(3.6)	(1.3)
Fair value	116.4	110.5
Commercial mortgage-backed securities
Fixed maturity investments
Cost or amortized cost	120.8	88.5
Gross unrealized gains	3.1	0.9
Gross unrealized (losses)	(1.7)	(0.6)
Net foreign currency gains (losses)	0.0	0.2
Fair value	122.2	89.0
Non-U.S. government and government agency
Fixed maturity investments
Cost or amortized cost	71.4	63.7
Gross unrealized gains	0.4	0.0
Gross unrealized (losses)	(0.1)	(0.7)
Net foreign currency gains (losses)	(0.6)	0.0
Fair value	71.1	63.0
Preferred stocks
Fixed maturity investments
Cost or amortized cost	14.9	17.0
Gross unrealized gains	3.1	0.0
Gross unrealized (losses)	(0.1)	0.0
Net foreign currency gains (losses)	0.0	0.0
Fair value	17.9	17.0
Cost or amortized cost
Cost or amortized cost without single maturity date	14.9	17.0
Fair value
Fair value without single maturity date	17.9	17.0
U.S. States, municipalities and political subdivision
Fixed maturity investments
Cost or amortized cost	1.2	1.7
Gross unrealized gains	0.1	0.0
Gross unrealized (losses)	0.0	0.0
Net foreign currency gains (losses)	0.0	0.0
Fair value	1.3	1.7
Mortgage-backed and asset-backed securities
Cost or amortized cost
Cost or amortized cost without single maturity date	1,254.6	1,004.1
Fair value
Fair value without single maturity date	1,270.3	1,014.7
Subprime | Fixed maturity investments
Fixed maturity investments
Fair value	43.8	43.3
Subprime | Fixed maturity investments | AAA
Fixed maturity investments
Fair value	21.5	21.7
Subprime | Fixed maturity investments | AA
Fixed maturity investments
Fair value	18.7	18.4
Subprime | Fixed maturity investments | A
Fixed maturity investments
Fair value	3.5	3.1
Subprime | Fixed maturity investments | Other
Fixed maturity investments
Fair value	$ 0.1	$ 0.1

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Investment securities - Equity securities and Other long-term investments (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Equity securities
Equity securities and Other long-term investments
Cost or amortized cost	$ 170.0	$ 379.2
Gross unrealized gains	27.8	55.6
Gross unrealized (losses)	(39.7)	(37.3)
Net foreign currency gains	0.6	7.7
Fair value	158.7	405.2
Other Long-term Investments
Equity securities and Other long-term investments
Cost or amortized cost	327.5	315.4
Gross unrealized gains	75.5	49.9
Gross unrealized (losses)	(24.4)	(29.3)
Net foreign currency gains	9.4	10.8
Fair value	388.0	346.8
Other Long-term Investments | Hedge funds and private equity funds
Equity securities and Other long-term investments
Fair value	301.1	269.0
Other Long-term Investments | Limited liability companies and private equity securities
Equity securities and Other long-term investments
Fair value	86.9	77.8
Fixed income mutual funds
Equity securities and Other long-term investments
Fair value	1.8	175.3
Common shares
Equity securities and Other long-term investments
Fair value	170.1	228.1
Other equity securities
Equity securities and Other long-term investments
Fair value	$ (13.2)	$ 1.8

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Investment securities - Hedge funds and Private equity funds (Details) - Other Long-term Investments $ in Millions	9 Months Ended
	Sep. 30, 2020 USD ($) fund	Dec. 31, 2019 USD ($)
Equity securities and Other long-term investments
Fair value	$ 388.0	$ 346.8
Long/short multi-sector
Equity securities and Other long-term investments
Fair value	54.9	53.0
Unfunded commitments	0.0	0.0
Distressed mortgage credit
Equity securities and Other long-term investments
Fair value	66.3	51.6
Unfunded commitments	0.0	0.0
Private credit
Equity securities and Other long-term investments
Fair value	22.1	21.5
Unfunded commitments	0.0	0.0
Multi-sector
Equity securities and Other long-term investments
Fair value	5.8	0.0
Unfunded commitments	0.0	0.0
Other
Equity securities and Other long-term investments
Fair value	1.2	1.4
Unfunded commitments	$ 0.0	0.0
Hedge funds
Equity securities and Other long-term investments
Number of investment funds in which the investments are held | fund	10
Fair value	$ 150.3	127.5
Unfunded commitments	0.0	0.0
Energy infrastructure & services
Equity securities and Other long-term investments
Fair value	56.6	53.6
Unfunded commitments	30.7	34.6
Multi-sector
Equity securities and Other long-term investments
Fair value	13.4	8.7
Unfunded commitments	8.1	7.8
Healthcare
Equity securities and Other long-term investments
Fair value	29.1	25.9
Unfunded commitments	6.3	10.4
Life settlement
Equity securities and Other long-term investments
Fair value	20.6	23.9
Unfunded commitments	0.0	0.0
Manufacturing/Industrial
Equity securities and Other long-term investments
Fair value	27.7	27.6
Unfunded commitments	0.0	3.9
Private equity secondaries
Equity securities and Other long-term investments
Fair value	0.6	0.6
Unfunded commitments	0.8	0.8
Other
Equity securities and Other long-term investments
Fair value	2.8	1.2
Unfunded commitments	$ 1.8	2.6
Private equity funds
Equity securities and Other long-term investments
Number of investment funds in which the investments are held | fund	32
Fair value	$ 150.8	141.5
Unfunded commitments	47.7	60.1
Hedge funds and private equity funds
Equity securities and Other long-term investments
Fair value	301.1	269.0
Unfunded commitments	$ 47.7	$ 60.1

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Investment securities - Hedge Funds redemption frequency and Private Equity Fund lock-up period (Details) - Other Long-term Investments - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Equity securities and Other long-term investments
Fair value	$ 388.0	$ 346.8
Hedge funds
Equity securities and Other long-term investments
Fair value	150.3	127.5
Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	36.3
Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	91.3
Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.3
Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	22.4
Private equity funds
Equity securities and Other long-term investments
Fair value	150.8	$ 141.5
Private equity funds | Lock up period of 1 - 3 years
Equity securities and Other long-term investments
Fair value	53.9
Private equity funds | Lock up period of 3 - 5 years
Equity securities and Other long-term investments
Fair value	19.0
Private equity funds | Lock up period of 5 - 10 years
Equity securities and Other long-term investments
Fair value	77.9
1-29 days notice | Hedge funds
Equity securities and Other long-term investments
Fair value	5.8
1-29 days notice | Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	5.8
1-29 days notice | Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
1-29 days notice | Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
1-29 days notice | Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
30-59 days notice | Hedge funds
Equity securities and Other long-term investments
Fair value	0.6
30-59 days notice | Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
30-59 days notice | Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.6
30-59 days notice | Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
30-59 days notice | Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
60-89 days notice | Hedge funds
Equity securities and Other long-term investments
Fair value	55.2
60-89 days notice | Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	30.5
60-89 days notice | Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	24.4
60-89 days notice | Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.3
60-89 days notice | Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
90-119 days notice | Hedge funds
Equity securities and Other long-term investments
Fair value	66.6
90-119 days notice | Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
90-119 days notice | Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	66.3
90-119 days notice | Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
90-119 days notice | Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.3
120+ days notice | Hedge funds
Equity securities and Other long-term investments
Fair value	22.1
120+ days notice | Hedge funds | Monthly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
120+ days notice | Hedge funds | Quarterly Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
120+ days notice | Hedge funds | Semi-annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	0.0
120+ days notice | Hedge funds | Annual Redemption Frequency
Equity securities and Other long-term investments
Fair value	$ 22.1

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Investment securities - Investments held on deposit or as collateral and Unsettled investment purchases and sales (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Marketable securities
Investments held in trusts	$ 1,202.9	$ 1,309.5
Investments held in trusts - fair value	1,217.9	1,315.5
Accounts payable
Marketable securities
Unsettled investment purchases	29.9	2.3
Accounts receivable
Marketable securities
Unsettled investment sales	19.2	6.7
Interest rate cap | Derivatives not designated as hedging instruments
Marketable securities
Collateral balances held	$ 0.1	$ 0.2

XML

Fair value measurements - Fair value measurements by level (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019	Sep. 30, 2019
Assets measured at fair value
Fixed maturity investments	$ 1,958.9	$ 1,681.0
Equity securities	158.7	405.2
Short-term investments	1,132.6	1,085.2
Other long term investments	86.9	77.8
Total investments	3,337.1	3,249.2
Derivative instruments	7.7	11.4
Total assets measured at fair value	3,373.3	3,280.6
Liabilities measured at fair value
Contingent consideration liabilities	0.3	28.2
Derivative instruments	3.6	9.5
Total liabilities measured at fair value	3.9	37.7
U.S. Government and government agency
Assets measured at fair value
Fixed maturity investments	116.4	110.5
Corporate debt securities
Assets measured at fair value
Fixed maturity investments	481.9	474.1
Residential mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	416.5	438.9
Asset-backed securities
Assets measured at fair value
Fixed maturity investments	731.6	486.8
Commercial mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	122.2	89.0
Non-U.S. government and government agency
Assets measured at fair value
Fixed maturity investments	71.1	63.0
Preferred stocks
Assets measured at fair value
Fixed maturity investments	17.9	17.0
U.S. States, municipalities, and political subdivision
Assets measured at fair value
Fixed maturity investments	1.3	1.7
Fixed income mutual funds
Assets measured at fair value
Equity securities	1.8	175.3
Common shares
Assets measured at fair value
Equity securities	170.1	228.1
Other equity securities
Assets measured at fair value
Equity securities	(13.2)	1.8
Hedge funds and private equity funds
Liabilities measured at fair value
Fair value of hedges	301.1	269.0	$ 287.7
Level 1 Inputs
Assets measured at fair value
Fixed maturity investments	136.2	140.8
Equity securities	155.0	403.4
Short-term investments	1,068.4	1,073.7
Other long term investments	0.0	0.0
Total investments	1,359.6	1,617.9
Derivative instruments	6.6	1.3
Total assets measured at fair value	1,366.2	1,619.2
Liabilities measured at fair value
Contingent consideration liabilities	0.0	0.0
Derivative instruments	0.1	0.2
Total liabilities measured at fair value	0.1	0.2
Level 1 Inputs | U.S. Government and government agency
Assets measured at fair value
Fixed maturity investments	115.4	109.1
Level 1 Inputs | Corporate debt securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | Residential mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | Asset-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | Commercial mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | Non-U.S. government and government agency
Assets measured at fair value
Fixed maturity investments	20.8	31.7
Level 1 Inputs | Preferred stocks
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | U.S. States, municipalities, and political subdivision
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 1 Inputs | Fixed income mutual funds
Assets measured at fair value
Equity securities	1.8	175.3
Level 1 Inputs | Common shares
Assets measured at fair value
Equity securities	170.1	228.1
Level 1 Inputs | Other equity securities
Assets measured at fair value
Equity securities	(16.9)	0.0
Level 2 Inputs
Assets measured at fair value
Fixed maturity investments	1,820.1	1,523.2
Equity securities	3.7	1.8
Short-term investments	64.2	11.5
Other long term investments	0.0	0.0
Total investments	1,888.0	1,536.5
Derivative instruments	0.0	0.0
Total assets measured at fair value	1,888.0	1,536.5
Liabilities measured at fair value
Contingent consideration liabilities	0.0	0.0
Derivative instruments	0.0	0.0
Total liabilities measured at fair value	0.0	0.0
Level 2 Inputs | U.S. Government and government agency
Assets measured at fair value
Fixed maturity investments	1.0	1.4
Level 2 Inputs | Corporate debt securities
Assets measured at fair value
Fixed maturity investments	481.9	474.1
Level 2 Inputs | Residential mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	416.5	438.9
Level 2 Inputs | Asset-backed securities
Assets measured at fair value
Fixed maturity investments	731.6	486.8
Level 2 Inputs | Commercial mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	122.2	89.0
Level 2 Inputs | Non-U.S. government and government agency
Assets measured at fair value
Fixed maturity investments	50.3	31.3
Level 2 Inputs | Preferred stocks
Assets measured at fair value
Fixed maturity investments	15.3	0.0
Level 2 Inputs | U.S. States, municipalities, and political subdivision
Assets measured at fair value
Fixed maturity investments	1.3	1.7
Level 2 Inputs | Fixed income mutual funds
Assets measured at fair value
Equity securities	0.0	0.0
Level 2 Inputs | Common shares
Assets measured at fair value
Equity securities	0.0	0.0
Level 2 Inputs | Other equity securities
Assets measured at fair value
Equity securities	3.7	1.8
Level 3 Inputs
Assets measured at fair value
Fixed maturity investments	2.6	17.0
Equity securities	0.0	0.0
Short-term investments	0.0	0.0
Other long term investments	86.9	77.8
Total investments	89.5	94.8
Derivative instruments	1.1	10.1
Total assets measured at fair value	119.1	124.9
Liabilities measured at fair value
Contingent consideration liabilities	0.3	28.2
Derivative instruments	3.5	9.3
Total liabilities measured at fair value	3.8	37.5
Level 3 Inputs | U.S. Government and government agency
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Corporate debt securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Residential mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Asset-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Commercial mortgage-backed securities
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Non-U.S. government and government agency
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Preferred stocks
Assets measured at fair value
Fixed maturity investments	2.6	17.0
Level 3 Inputs | U.S. States, municipalities, and political subdivision
Assets measured at fair value
Fixed maturity investments	0.0	0.0
Level 3 Inputs | Fixed income mutual funds
Assets measured at fair value
Equity securities	0.0	0.0
Level 3 Inputs | Common shares
Assets measured at fair value
Equity securities	0.0	0.0
Level 3 Inputs | Other equity securities
Assets measured at fair value
Equity securities	0.0	0.0
Loan participation
Assets measured at fair value
Loan participation	28.5	20.0
Loan participation | Level 1 Inputs
Assets measured at fair value
Loan participation	0.0	0.0
Loan participation | Level 2 Inputs
Assets measured at fair value
Loan participation	0.0	0.0
Loan participation | Level 3 Inputs
Assets measured at fair value
Loan participation	$ 28.5	$ 20.0

XML

Fair value measurements - Rollforward of level 3 fair value measurements (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Rollforward of Level 3, Derivative instruments assets & (liabilities)
Balance at beginning of the period	$ 1.5	$ (3.6)	$ 0.8	$ (0.5)
Total realized and unrealized gains (losses)	(1.7)	(2.0)	(20.7)	(7.7)
Purchases	0.0	0.0	0.0	0.0
Sales/Settlements(2)	(2.2)	3.4	17.5	6.0
Balance at end of the period	(2.4)	(2.2)	(2.4)	(2.2)
Rollforward of Level 3, (liabilities)
Payment of contingent consideration			28.4	0.0
IMG
Rollforward of Level 3, (liabilities)
Payment of contingent consideration	18.4	6.9	18.4	6.9
Armada
Rollforward of Level 3, (liabilities)
Payment of contingent consideration	4.5		10.0
Hedge funds and private equity funds
Rollforward of Level 3, (liabilities)
Fair value of hedges	301.1	287.7	301.1	287.7	$ 269.0
Fixed maturity investments
Rollforward of Level 3 Fair Value Measurements
Balance at beginning of the period	2.6	0.0	17.0	5.4
Total realized and unrealized gains (losses)	0.0	0.0	2.6	0.0
Purchases	0.0	17.0	0.0	17.0
Sales/Settlements(2)	0.0	0.0	(17.0)	(5.4)
Balance at end of the period	2.6	17.0	2.6	17.0
Other Long-term Investments
Rollforward of Level 3 Fair Value Measurements
Balance at beginning of the period	78.2	88.0	77.8	63.6
Total realized and unrealized gains (losses)	8.2	(0.3)	3.1	10.6
Purchases	0.0	0.0	5.5	15.8
Sales/Settlements(2)	0.0	(6.0)	0.0	(7.8)
Balance at end of the period	86.9	80.7	86.9	80.7
Loan participation
Rollforward of Level 3 Fair Value Measurements
Balance at beginning of the period	27.3	0.0	20.0	0.0
Total realized and unrealized gains (losses)	0.0	0.0	0.0	0.0
Purchases	2.5	0.0	9.9	0.0
Sales/Settlements(2)	(1.3)	0.0	(1.4)	0.0
Balance at end of the period	28.5	0.0	28.5	0.0
Contingent consideration (liabilities)
Rollforward of Level 3, (liabilities)
Balance at beginning of the period	(22.9)	(30.8)	(28.2)	(28.8)
Total realized and unrealized gains (losses)	(0.3)	(2.1)	(0.5)	(4.1)
Foreign currency gains (losses) through Other Comprehensive Income	0.0	0.0	0.0	0.0
Purchases	0.0	0.0	0.0	0.0
Sales/Settlements	22.9	6.9	28.4	6.9
Balance at end of the period	(0.3)	(26.0)	(0.3)	(26.0)
Foreign currency gains through Other Comprehensive Income
Rollforward of Level 3, Derivative instruments assets & (liabilities)
Foreign currency gains through Other Comprehensive Income	0.0	0.0	0.0	0.0
Foreign currency gains through Other Comprehensive Income | Fixed maturity investments
Rollforward of Level 3 Fair Value Measurements
Foreign currency gains through Other Comprehensive Income	0.0	0.0	0.0	0.0
Foreign currency gains through Other Comprehensive Income | Other Long-term Investments
Rollforward of Level 3 Fair Value Measurements
Foreign currency gains through Other Comprehensive Income	0.5	(1.0)	0.5	(1.5)
Foreign currency gains through Other Comprehensive Income | Loan participation
Rollforward of Level 3 Fair Value Measurements
Foreign currency gains through Other Comprehensive Income	$ 0.0	$ 0.0	$ 0.0	$ 0.0

XML

Fair value measurements - Transfers between levels (Details) - USD ($)	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Fair Value Disclosures [Abstract]
Transfers between level 3 and level 2	$ 0	$ 0	$ 0	$ 0

XML

Fair value measurements - Significant unobservable inputs (Details)	Sep. 30, 2020 USD ($) $ / shares	Dec. 31, 2019 USD ($) $ / shares
Significant Unobservable Inputs
Equity securities	$ 158,700,000	$ 405,200,000
Derivative assets	7,700,000	11,400,000
Derivative liabilities	(3,600,000)	(9,500,000)
Contingent consideration	(300,000)	(28,200,000)
Level 3 Inputs
Significant Unobservable Inputs
Equity securities	0	0
Derivative assets	1,100,000	10,100,000
Derivative liabilities	(3,500,000)	(9,300,000)
Contingent consideration	(300,000)	(28,200,000)
Level 3 Inputs | Private debt instrument
Significant Unobservable Inputs
Debt securities, trading	6,200,000
Level 3 Inputs | Share price of recent transaction | Private equity securities
Significant Unobservable Inputs
Equity securities		32,500,000
Level 3 Inputs | Share price of recent transaction | Preferred stock
Significant Unobservable Inputs
Equity securities		$ 17,500,000
Level 3 Inputs | Share price of recent transaction | Private equity securities
Significant Unobservable Inputs
Equity securities	$ 4,700,000
Level 3 Inputs | Share price of recent transaction | Purchase price | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		40.6
Level 3 Inputs | Share price of recent transaction | Purchase price | Preferred stock
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		7.74
Level 3 Inputs | Share price of recent transaction | Purchase price | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares	7.74
Level 3 Inputs | Purchase price of recent transaction | Private equity securities
Significant Unobservable Inputs
Equity securities	$ 32,500,000
Level 3 Inputs | Purchase price of recent transaction | Preferred stock
Significant Unobservable Inputs
Equity securities	27,900,000
Level 3 Inputs | Purchase price of recent transaction | Loan participation
Significant Unobservable Inputs
Equity securities	18,500,000	$ 20,000,000.0
Level 3 Inputs | Purchase price of recent transaction | Loan participation
Significant Unobservable Inputs
Equity securities	10,000,000.0
Level 3 Inputs | Purchase price of recent transaction | Private debt instrument
Significant Unobservable Inputs
Debt securities, trading		7,200,000
Level 3 Inputs | Purchase price of recent transaction | Private equity securities
Significant Unobservable Inputs
Equity securities		1,000,000.0
Level 3 Inputs | Purchase price of recent transaction | private equity securities
Significant Unobservable Inputs
Equity securities		300,000
Level 3 Inputs | Purchase price of recent transaction | Preferred stock
Significant Unobservable Inputs
Equity securities		12,200,000
Derivative assets	1,900,000
Level 3 Inputs | Purchase price of recent transaction | Preferred stock
Significant Unobservable Inputs
Equity securities	700,000	4,800,000
Level 3 Inputs | Purchase price of recent transaction | Private equity funds
Significant Unobservable Inputs
Equity securities	$ 300,000	$ 5,100,000
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares	40.63
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Preferred stock
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares	7.74
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		20,000,000.0
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Private debt instrument
Significant Unobservable Inputs
Private debt instrument, measurement input, value		$ 9,000,000.0
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		10.0
Level 3 Inputs | Purchase price of recent transaction | Purchase price | private equity securities
Significant Unobservable Inputs
Equity securities, measurement input, value		$ 300,000
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Preferred stock
Significant Unobservable Inputs
Derivative assets, measurement input, value	$ 1,900,000
Equity securities, measurement input, value		12,200,000
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Preferred stock
Significant Unobservable Inputs
Equity securities, measurement input, value	700,000	$ 4,800,000
Level 3 Inputs | Purchase price of recent transaction | Purchase price | Private equity funds
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		7.74
Equity securities, measurement input, value	300,000
Level 3 Inputs | Multiple of GAAP book value | Private equity securities
Significant Unobservable Inputs
Equity securities	13,300,000	$ 14,200,000
Level 3 Inputs | Multiple of GAAP book value | Book value multiple | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share) | $ / shares		0.9
Level 3 Inputs | Unit price of recent transaction | Private convertible debt instrument
Significant Unobservable Inputs
Equity securities	2,000,000.0
Level 3 Inputs | Unit price of recent transaction | Purchase price | Private convertible debt instrument
Significant Unobservable Inputs
Equity securities, measurement input, value	7.74
Level 3 Inputs | Option pricing model | Equity warrants
Significant Unobservable Inputs
Equity securities		$ 400,000
Derivative assets	500,000
Level 3 Inputs | Option pricing model | Strike price | Equity warrants
Significant Unobservable Inputs
Derivative assets, measurement input, value	200,000
Equity securities, measurement input, value		200,000
Level 3 Inputs | Third party appraisal | Foreign currency swaps
Significant Unobservable Inputs
Derivative liabilities		(3,600,000)
Level 3 Inputs | Third party appraisal | Foreign currency swaps | Foreign currency swaps
Significant Unobservable Inputs
Equity securities	300,000
Level 3 Inputs | Third party appraisal | Foreign currency forwards
Significant Unobservable Inputs
Derivative assets		2,700,000
Level 3 Inputs | Third party appraisal | Weather derivatives
Significant Unobservable Inputs
Derivative assets		7,000,000.0
Contingent consideration	(3,500,000)
Level 3 Inputs | Third party appraisal | Currency forwards
Significant Unobservable Inputs
Derivative liabilities		(5,700,000)
Level 3 Inputs | Third party appraisal | Currency forwards | Foreign currency forwards
Significant Unobservable Inputs
Equity securities	300,000
Level 3 Inputs | Third party appraisal | Broker quote | Foreign currency swaps
Significant Unobservable Inputs
Derivative liabilities, measurement input, value		(3,600,000)
Level 3 Inputs | Third party appraisal | Broker quote | Foreign currency swaps | Foreign currency swaps
Significant Unobservable Inputs
Equity securities, measurement input, value	300,000
Level 3 Inputs | Third party appraisal | Broker quote | Foreign currency forwards
Significant Unobservable Inputs
Derivative assets, measurement input, value		2,700,000
Level 3 Inputs | Third party appraisal | Broker quote | Weather derivatives
Significant Unobservable Inputs
Derivative assets, measurement input, value		7,000,000.0
Contingent consideration, measurement input, value	(3,500,000)
Level 3 Inputs | Third party appraisal | Broker quote | Currency forwards
Significant Unobservable Inputs
Derivative liabilities, measurement input, value		(5,700,000)
Level 3 Inputs | Third party appraisal | Broker quote | Currency forwards | Foreign currency forwards
Significant Unobservable Inputs
Equity securities, measurement input, value	300,000
Level 3 Inputs | External valuation model
Significant Unobservable Inputs
Derivative liabilities	(300,000)
Level 3 Inputs | External valuation model | Contingent consideration
Significant Unobservable Inputs
Contingent consideration		(28,200,000)
Level 3 Inputs | External valuation model | Discounted future payment
Significant Unobservable Inputs
Derivative liabilities, measurement input, value	$ (300,000)
Level 3 Inputs | External valuation model | Discounted future payment | Contingent consideration
Significant Unobservable Inputs
Contingent consideration, measurement input, value		$ (28,200,000)
Minimum | Level 3 Inputs | Discount yield | Private debt instrument
Significant Unobservable Inputs
Debt securities, trading, measurement input	0.1187
Minimum | Level 3 Inputs | Purchase price of recent transaction | Comparability yields | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0446
Minimum | Level 3 Inputs | Purchase price of recent transaction | Purchase price | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0446
Minimum | Level 3 Inputs | Multiple of GAAP book value | Book value multiple | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.73
Maximum | Level 3 Inputs | Discount yield | Private debt instrument
Significant Unobservable Inputs
Debt securities, trading, measurement input	0.1232
Maximum | Level 3 Inputs | Purchase price of recent transaction | Comparability yields | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0782
Maximum | Level 3 Inputs | Purchase price of recent transaction | Purchase price | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0782
Maximum | Level 3 Inputs | Multiple of GAAP book value | Book value multiple | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.91
Median | Level 3 Inputs | Discount yield | Private debt instrument
Significant Unobservable Inputs
Debt securities, trading, measurement input	0.1208
Median | Level 3 Inputs | Purchase price of recent transaction | Comparability yields | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0574
Median | Level 3 Inputs | Purchase price of recent transaction | Purchase price | Loan participation
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.0574
Median | Level 3 Inputs | Multiple of GAAP book value | Book value multiple | Private equity securities
Significant Unobservable Inputs
Equity securities, measurement input (in dollars per share)	0.82

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Fair value measurements - Financial instruments disclosed, but not carried at fair value (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Financial instruments not carried at fair value
Debt	$ 695.8	$ 685.2
Carrying Value | Series B preference shares
Financial instruments not carried at fair value
Redeemable preference shares	197.5	223.0
2017 SEK Subordinated Notes
Financial instruments not carried at fair value
Debt	301.3	291.2
2017 SEK Subordinated Notes | Carrying Value
Financial instruments not carried at fair value
Debt	301.3	291.2
2016 SIG Senior Notes
Financial instruments not carried at fair value
Debt	394.5	394.0
2016 SIG Senior Notes | Carrying Value
Financial instruments not carried at fair value
Debt	394.5	394.0
Level 3 Inputs | Fair Value | Series B preference shares
Financial instruments not carried at fair value
Redeemable preference shares	244.5	186.4
Level 3 Inputs | 2017 SEK Subordinated Notes | Fair Value
Financial instruments not carried at fair value
Debt	298.8	294.5
Level 3 Inputs | 2016 SIG Senior Notes | Fair Value
Financial instruments not carried at fair value
Debt	$ 394.7	$ 394.5

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Debt and standby letters of credit facilities (Details)	Sep. 30, 2020 USD ($)	Dec. 31, 2019 USD ($)	Sep. 22, 2017 USD ($)	Sep. 22, 2017 SEK (kr)	Nov. 01, 2016 USD ($)
Debt and standby letters of credit facilities
Long-term debt, total	$ 695,800,000	$ 685,200,000
2017 SEK Subordinated Notes
Debt and standby letters of credit facilities
Debt, at face value	305,000,000.0	295,000,000.0	$ 346,100,000	kr 2,750,000,000.0
Unamortized issuance costs	(3,700,000)	(3,800,000)
Long-term debt, total	$ 301,300,000	$ 291,200,000
Effective rate	4.30%	4.00%
2016 SIG Senior Notes
Debt and standby letters of credit facilities
Debt, at face value	$ 400,000,000.0	$ 400,000,000.0			$ 400,000,000.0
Unamortized issuance costs	(3,400,000)	(3,700,000)
Unamortized discount	(2,100,000)	(2,300,000)
Long-term debt, total	$ 394,500,000	$ 394,000,000.0
Effective rate	4.70%	4.70%

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Debt and standby letters of credit facilities - 2017 SEK Subordinated Notes and 2016 SIG Senior Notes (Details)				3 Months Ended		9 Months Ended
	Sep. 22, 2017 USD ($)	Sep. 22, 2017 SEK (kr)	Nov. 01, 2016 USD ($)	Sep. 30, 2020 USD ($)	Sep. 30, 2019 USD ($)	Sep. 30, 2020 USD ($)	Sep. 30, 2019 USD ($)	Dec. 31, 2019 USD ($)	Sep. 22, 2017 SEK (kr)
Debt and standby letters of credit facilities
Interest expense on debt				$ 8,100,000	$ 7,700,000	$ 23,800,000	$ 23,300,000
2017 SEK Subordinated Notes
Debt and standby letters of credit facilities
Debt notes issued	$ 346,100,000			305,000,000.0		305,000,000.0		$ 295,000,000.0	kr 2,750,000,000.0
Issue price (as a percent)	100.00%	100.00%
Term of redemption following occurrence of Specified Event (in days)	90 days	90 days
Debt issuance costs	$ 4,600,000
Underwriting fees	$ 3,500,000	kr 27,500,000
Foreign currency exchange (losses) gains on remeasurement of debt				$ (10,700,000)	$ 15,900,000	$ (9,900,000)	$ 27,200,000
Effective rate				4.30%	4.10%	4.30%	4.00%
Interest expense on debt				$ 3,300,000	$ 3,000,000.0	$ 9,400,000	$ 8,900,000
Effective rate				4.30%		4.30%		4.00%
2016 SIG Senior Notes
Debt and standby letters of credit facilities
Debt notes issued			$ 400,000,000.0	$ 400,000,000.0		$ 400,000,000.0		$ 400,000,000.0
Issue price (as a percent)			99.209%
Debt issuance costs			$ 5,100,000
Underwriting fees			3,400,000
Interest expense on debt				$ 4,800,000	$ 4,800,000	$ 14,400,000	$ 14,400,000
Net proceeds			$ 392,400,000
Annual interest rate (as a percent)			4.60%
Effective rate				4.70%		4.70%		4.70%

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Debt and standby letters of credit facilities - Standby Letter of Credit Facilities (Details) kr in Billions	Sep. 30, 2020 USD ($)	Sep. 30, 2020 SEK (kr)	Dec. 31, 2019 USD ($)	Dec. 31, 2019 SEK (kr)	Nov. 09, 2019 USD ($) letter_of_credit
Standby Letter of Credit Facilities
Number of standby letter of credit agreements renewed | letter_of_credit					2
Other secured letter of credit and trust arrangement | Sirius america insurance company
Standby Letter of Credit Facilities
Secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust	$ 47,900,000		$ 57,700,000
Other secured letter of credit and trust arrangement | Sirius bermuda insurance company ltd.
Standby Letter of Credit Facilities
Secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust	519,900,000		784,000,000.0
Sirius International | Nordea bank finland abp
Standby Letter of Credit Facilities
Borrowing capacity					$ 90,000,000
Sirius International | DNB bank ASA london branch
Standby Letter of Credit Facilities
Borrowing capacity					35,000,000
Sirius International | Standby letters of credit
Standby Letter of Credit Facilities
Borrowing capacity					125,000,000
Sirius International | Unsecured standby letters of credit | DNB bank ASA london branch
Standby Letter of Credit Facilities
Borrowing capacity					$ 25,000,000
Sirius International | Other secured letter of credit and trust arrangement
Standby Letter of Credit Facilities
Secured letter of credit and trust arrangements were collateralized by pledged assets and assets in trust	$ 488,300,000	kr 4.4	$ 363,300,000	kr 3.4

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Debt and standby letters of credit facilities - Revolving Credit Facility (Details) - USD ($)	1 Months Ended
	Feb. 28, 2018	Sep. 30, 2020
Line of Credit Facility [Line Items]
Outstanding amount		$ 0
Revolving credit facility
Line of Credit Facility [Line Items]
Debt instrument, term	3 years
Borrowing capacity	$ 300,000,000

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Debt and standby letters of credit facilities - Interest (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Debt Disclosure [Abstract]
Interest expense on debt	$ 8.1	$ 7.7	$ 23.8	$ 23.3
Total interest paid	$ 3.3	$ 2.8	$ 18.5	$ 17.7

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Income taxes (Details) - USD ($)	3 Months Ended		9 Months Ended		12 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Income Tax Disclosure [Abstract]
Income tax expense (benefit)	$ 23,500,000	$ (3,700,000)	$ 19,900,000	$ 15,600,000
Pre-tax income (loss)	$ (80,500,000)	$ (11,300,000)	(212,600,000)	$ 120,300,000
Provision for income taxes related to BEAT			0		$ 0
Provision for income taxes related to GILTI			$ 0		$ 0

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Income taxes - Deferred tax asset, net of valuation allowance and Uncertain tax positions (Details) $ in Millions	Sep. 30, 2020 USD ($)
Income taxes
Net deferred tax liability, net of valuation allowance	$ 55.1
Other net deferred tax liabilities	7.6
Uncertain tax positions
Total reserve for unrecognized tax benefits	47.5
Reversal of reserves for unrecognized tax benefits on permanent differences and interest and penalties	47.3
Reversal of reserves for unrecognized tax benefits on temporary differences	0.2
U.S. subsidiaries
Income taxes
Net deferred tax assets	25.0
Luxembourg subsidiaries
Income taxes
Net deferred tax assets	141.3
Sweden subsidiaries
Income taxes
Net deferred tax assets	213.8
Sweden subsidiaries | Swedish tax authority
Uncertain tax positions
Reserve attributable to uncertain tax positions	$ 46.6

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Derivatives - Interest rate cap (Details) - Interest rate cap $ in Millions	9 Months Ended
	Sep. 30, 2020 USD ($) financial_institution	Dec. 31, 2019 USD ($)
Derivatives
Number of financial institutions entered into derivative contracts | financial_institution	2
Derivatives not designated as hedging instruments
Derivatives
Collateral balances held | $	$ 0.1	$ 0.2

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Derivatives - Classification and fair value of derivatives in consolidated balance sheets (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Derivatives
Derivative assets	$ 7.7	$ 11.4
Derivative liabilities	3.6	9.5
Interest rate cap | Derivatives not designated as hedging instruments
Derivatives
Notional Value	250.0	250.0
Interest rate cap | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.0	0.0
Interest rate cap | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	0.0
Foreign currency swaps | Derivatives not designated as hedging instruments
Derivatives
Notional Value	40.0	90.0
Foreign currency swaps | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.3	0.0
Foreign currency swaps | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	3.6
Foreign currency forwards | Derivatives not designated as hedging instruments
Derivatives
Notional Value	225.2	30.0
Foreign currency forwards | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.3	2.7
Foreign currency forwards | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	5.7
Weather derivatives | Derivatives not designated as hedging instruments
Derivatives
Notional Value	53.6	110.7
Weather derivatives | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.0	7.0
Weather derivatives | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	3.5	0.0
Equity futures contracts | Derivatives not designated as hedging instruments
Derivatives
Notional Value	1.0	34.5
Equity futures contracts | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.0	0.0
Equity futures contracts | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	0.0
Foreign currency futures contracts | Derivatives not designated as hedging instruments
Derivatives
Notional Value	22.3	0.0
Foreign currency futures contracts | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.0	0.0
Foreign currency futures contracts | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	0.0
Equity call options | Derivatives not designated as hedging instruments
Derivatives
Notional Value	34.6	0.0
Equity call options | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	2.5	0.0
Equity call options | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	0.0
Equity put options | Derivatives not designated as hedging instruments
Derivatives
Notional Value	77.3	31.0
Equity put options | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	1.9	1.3
Equity put options | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.1	0.2
Foreign currency call options | Derivatives not designated as hedging instruments
Derivatives
Notional Value	50.6	0.0
Foreign currency call options | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	2.2	0.0
Foreign currency call options | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	0.0	0.0
Equity warrants | Derivatives not designated as hedging instruments
Derivatives
Notional Value	0.5	0.4
Equity warrants | Derivatives not designated as hedging instruments | Other assets
Derivatives
Derivative assets	0.5	0.4
Equity warrants | Derivatives not designated as hedging instruments | Other liabilities
Derivatives
Derivative liabilities	$ 0.0	$ 0.0

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Derivatives - Classification and fair value of derivatives in consolidated of (loss) income statements (Details) - Derivatives not designated as hedging instruments - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Interest rate cap | Other revenues
Derivatives
Gains (losses) recognized in earnings	$ 0.0	$ 0.0	$ 0.0	$ (0.2)
Foreign currency swaps | Net foreign exchange (losses) gains
Derivatives
Gains (losses) recognized in earnings	(0.9)	3.7	1.8	6.1
Foreign currency forwards | Net foreign exchange (losses) gains
Derivatives
Gains (losses) recognized in earnings	(0.4)	(7.8)	(0.9)	(10.8)
Weather derivatives | Other revenues
Derivatives
Gains (losses) recognized in earnings	(0.4)	1.9	(21.8)	(3.6)
Equity futures contracts | Net realized investment (losses) gains
Derivatives
Gains (losses) recognized in earnings	(0.2)	0.1	2.4	(0.7)
Equity futures contracts | Net unrealized investment gains (losses)
Derivatives
Gains (losses) recognized in earnings	(0.1)	(0.5)	0.4	(0.6)
Foreign currency futures contracts | Net foreign exchange (losses) gains
Derivatives
Gains (losses) recognized in earnings	0.8	0.0	0.1	0.0
Equity put options | Net realized investment (losses) gains
Derivatives
Gains (losses) recognized in earnings	1.9	(0.8)	7.8	(0.8)
Equity put options | Net unrealized investment gains (losses)
Derivatives
Gains (losses) recognized in earnings	(0.6)	0.7	0.8	0.2
Foreign currency call options | Net foreign exchange (losses) gains
Derivatives
Gains (losses) recognized in earnings	1.0	0.0	0.8	0.0
Equity warrants | Net unrealized investment gains (losses)
Derivatives
Gains (losses) recognized in earnings	$ (0.1)	$ 0.3	$ 0.1	$ 0.7

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Share-based compensation - Narrative (Details) - USD ($) $ in Millions		3 Months Ended		9 Months Ended
	Mar. 15, 2020	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Compensation expense		$ (3.3)	$ 3.0	$ 0.7	$ 3.1
Amount paid to employees for share-based awards		$ 1.9	1.9	$ 3.3	3.3
Unrecognized share-based compensation costs			$ 27.1		$ 27.1
Options granted in the period (in shares)		0		0	1,374,944
Retention program expense		$ 1.6		$ 9.2
Minimum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Weighted average recognition period (years)					2 years
Maximum
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Weighted average recognition period (years)					3 years
Restricted stock | Board of Directors Chairman
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Awards granted in the period (in shares)			2,424		37,039
Performance share units
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Awards granted in the period (in shares)			7,059		408,370
Forfeited (in shares)			43,230		57,565
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Weighted average recognition period (years)				1 year 3 months 18 days
Awards granted in the period (in shares)		0	16,471	0	1,428,185
Forfeited (in shares)		1,060	25,936	80,160	71,988
Retention awards
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Awards granted under the retention program	$ 13.8
Amount paid for retention awards	$ 6.9
Long term incentive plan 2020 | Performance share units
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Compensation expense		$ 1.1		$ 4.2
Long term incentive plan 2020 | RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Compensation expense		$ 6.1

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Share-based compensation - Unrecognized Compensation Cost and Period Of Recognition (Details) $ in Millions	9 Months Ended
	Sep. 30, 2020 USD ($)
RSUs
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost related to unvested awards	$ 6.4
Weighted average recognition period (years)	1 year 3 months 18 days
Stock Options
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unrecognized compensation cost related to unvested awards	$ 1.3
Weighted average recognition period (years)	1 year 6 months

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Share-based compensation - Unvested Share-based Awards Activity (Details) - shares	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding [Roll Forward]
Unvested, beginning of the year (in shares)	1,374,945		1,374,945
Granted (in shares)	0		0	1,374,944
Vested (in shares)	0		0
Forfeited (in shares)	0		0
Unvested, end of the year (in shares)	1,374,945		1,374,945
Performance share units
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]
Granted (in shares)		7,059		408,370
Shares forfeited (in shares)		43,230		57,565
RSUs
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]
Unvested, beginning of the year (in shares)	1,274,752		1,353,852
Granted (in shares)	0	16,471	0	1,428,185
Vested (in shares)	0		0
Shares forfeited (in shares)	1,060	25,936	80,160	71,988
Unvested, end of the year (in shares)	1,273,692		1,273,692

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Common shareholder's equity, mezzanine equity, and non controlling interests - Common shareholder's equity (Details) - $ / shares	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Common shareholder's equity
Common shares authorized (in shares)	500,000,000		500,000,000
Common shares par value (in dollars per share)	$ 0.01		$ 0.01
Preference shares authorized / designated ( in shares)	100,000,000		100,000,000
Preference shares par value (in dollars per share)	$ 0.01		$ 0.01
Changes in common shareholders' equity
Shares issued, beginning of period (in shares)	115,299,341	115,296,918	115,299,341	115,151,251
Shares outstanding, beginning of period (in shares)	115,299,341	115,296,918	115,299,341	115,151,251
Issuance of shares to directors and employees (in shares)	0	2,424	0	148,091
Shares issued, end of period (in shares)	115,299,341	115,299,342	115,299,341	115,299,342
Shares outstanding, end of period (in shares)	115,299,341	115,299,342	115,299,341	115,299,342

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Common shareholder's equity, mezzanine equity, and non controlling interests - Mezzanine equity (Details) - USD ($) $ / shares in Units, $ in Millions	9 Months Ended
	Sep. 30, 2020	Dec. 31, 2019	Nov. 05, 2018
Mezzanine equity
Preference shares authorized / designated ( in shares)	100,000,000
Preference shares par value (in dollars per share)	$ 0.01
Carrying value of preference shares	$ 197.5	$ 223.0
Series B preference shares
Mezzanine equity
Preference shares authorized / designated ( in shares)			15,000,000
Preference shares par value (in dollars per share)			$ 0.01
Preferential rights, aggregate gross proceeds from the issuance of senior or pari passu shares	$ 100.0
Series B preference shares | Sirius group private placement | Preference share investors
Mezzanine equity
Share subscriptions (in shares)			11,901,670

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Common shareholder's equity, mezzanine equity, and non controlling interests - Non-controlling interests (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Common shareholder's equity, mezzanine equity, and non-controlling interests
Non-controlling interests	$ 2.5	$ 3.4	$ 2.4	$ 1.7
Change in non-controlling interest
Non-controlling interests, beginning of the period	2.5	3.0	2.4	1.7
Net income attributable to non-controlling interests	0.2	0.4	0.2	1.6
Dividends paid	(1.0)	0.0	(1.0)	0.0
Other, net	0.1	0.0	0.2	0.1
Non-controlling interests, end of the period	1.8	$ 3.4	1.8	$ 3.4
Alstead Re
Common shareholder's equity, mezzanine equity, and non-controlling interests
Non-controlling interests	1.8		2.3
Change in non-controlling interest
Non-controlling interests, beginning of the period			2.3
Non-controlling interests, end of the period	$ 1.8		$ 1.8

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Earnings per share - Basic and Diluted earnings per share (Details) - USD ($) $ / shares in Units, $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Numerator:
Net Income (Loss), Including Portion Attributable to Noncontrolling Interest	$ (104.0)	$ (7.6)	$ (232.5)	$ 104.7
Less: Income attributable to non-controlling interests	(0.2)	(0.4)	(0.2)	(1.6)
Less: Change in carrying value of Series B preference shares	8.7	5.3	25.5	(3.9)
Net (loss) income attributable to Sirius Group's common shareholders	(95.5)	(2.7)	(207.2)	99.2
Less: Earnings attributable to Series B preference shares	0.0	0.0	0.0	(9.3)
Net income available to Sirius Group common shareholders	(95.5)	(2.7)	(207.2)	89.9
Add: Change in carrying value of Series B preference shares	0.0	(5.3)	(25.5)	0.0
Net income available to Sirius Group common shareholders on a diluted basis	$ (95.5)	$ (8.0)	$ (232.7)	$ 89.9
Denominator:
Basic earnings per share (in dollars per share)	$ (0.83)	$ (0.02)	$ (1.80)	$ 0.78
Weighted average shares outstanding for basic earnings per share (in shares)	115,297,945	115,251,853	115,279,197	115,225,942
Add: Series B preference shares (in shares)	0	11,901,670	11,901,670	0
Add: Unvested performance share units and restricted share units (in shares)	0	0	0	393,280
Weighted average shares outstanding for diluted earnings per share (in shares)	115,297,945	127,153,523	127,180,867	115,619,222
Diluted earnings per share (in dollars per share)	$ (0.83)	$ (0.06)	$ (1.83)	$ 0.78
Potentially dilutive securities excluded from the calculation of diluted earnings per share (in shares)	26,057,275	19,537,270	14,155,605	31,045,660

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Investments in unconsolidated entities - Other long-term investments (Details) - USD ($)	Sep. 30, 2020	Dec. 31, 2019
Investments in unconsolidated entities
Other long-term investments	$ 388,000,000.0	$ 346,800,000
Equity method investments	0	0
Investments in unconsolidated entities
Investments in unconsolidated entities
Other long-term investments	388,000,000.0	346,800,000
Investments in unconsolidated entities | Equity method eligible investments
Investments in unconsolidated entities
Other long-term investments	166,800,000	151,900,000
Investments in unconsolidated entities | Equity method ineligible investments
Investments in unconsolidated entities
Other long-term investments	$ 221,200,000	$ 194,900,000

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Investments in unconsolidated entities - Equity method unconsolidated entities (Details) - Investments in unconsolidated entities - Equity method eligible investments	9 Months Ended	12 Months Ended
	Sep. 30, 2020	Dec. 31, 2019
BE Reinsurance Limited
Investments in unconsolidated entities
Ownership interest	24.90%	24.90%
BioVentures Investors (Offshore) IV LP
Investments in unconsolidated entities
Ownership interest	73.00%	73.00%
Camden Partners Strategic Fund V (Cayman), LP
Investments in unconsolidated entities
Ownership interest	39.40%	39.40%
Diamond LS I LP
Investments in unconsolidated entities
Ownership interest	15.60%	16.00%
Gateway Fund LP
Investments in unconsolidated entities
Ownership interest	22.90%	15.00%
Monarch
Investments in unconsolidated entities
Ownership interest	12.80%	12.80%
New Energy Capital Infrastructure Credit Fund LP
Investments in unconsolidated entities
Ownership interest	29.80%	30.50%
New Energy Capital Infrastructure Offshore Credit Fund LP
Investments in unconsolidated entities
Ownership interest	29.80%	30.50%
Pie Preferred Stock
Investments in unconsolidated entities
Ownership interest	30.10%	30.10%
Pie Series B Preferred Stock
Investments in unconsolidated entities
Ownership interest	23.40%	22.40%
Quintana Energy Partners
Investments in unconsolidated entities
Ownership interest	21.80%	21.80%
Tuckerman Capital V LP
Investments in unconsolidated entities
Ownership interest	48.30%	48.30%
Tuckerman Capital V Co-Investment I LP
Investments in unconsolidated entities
Ownership interest	48.30%	48.10%

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Variable interest entities (Details) - USD ($) $ in Millions	Sep. 30, 2020	Jun. 30, 2020	Dec. 31, 2019	Sep. 30, 2019	Jun. 30, 2019	Dec. 31, 2018
Assets:
Fixed maturity investments	$ 1,958.9		$ 1,681.0
Short-term investments	1,132.6		1,085.2
Cash	168.4		136.3
Insurance and reinsurance premiums receivable	(789.0)		(730.1)
Funds held by ceding companies	244.1		293.9
Deferred acquisition costs	145.2		148.2
Other assets	151.5		161.4
Total assets	6,632.8		6,413.8
Liabilities
Loss and loss adjustment expense reserves	2,672.9	$ 2,515.1	2,331.5	$ 2,186.4	$ 2,023.3	$ 2,016.7
Unearned insurance and reinsurance premiums	759.4		708.0
Other liabilities	175.9		201.3
Total liabilities	4,974.3		4,548.0
VIEs
Assets:
Fixed maturity investments	3.8		3.9
Short-term investments	0.5		0.5
Cash	0.1		0.1
Total investments	4.3		4.5
Insurance and reinsurance premiums receivable	(0.5)		(0.3)
Funds held by ceding companies	2.3		3.4
Deferred acquisition costs	0.0		0.3
Other assets	0.0		0.0
Total assets	6.2		7.9
Liabilities
Loss and loss adjustment expense reserves	0.3		0.5
Unearned insurance and reinsurance premiums	0.0		0.6
Other liabilities	0.1		0.1
Total liabilities	$ 0.4		$ 1.2

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Variable interest entities - Unconsolidated VIE (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Total VIE Assets
Total VIE Assets	$ 388.0	$ 346.8
Total assets	6,632.8	6,413.8
Unconsolidated VIE
Total VIE Assets
Total VIE Assets	254.8	257.8
Total assets	254.8	257.8
On-Balance Sheet | Unconsolidated VIE
Total VIE Assets
Maximum Exposure to Loss	117.1	102.6
Total assets	117.1	102.6
Off-Balance Sheet | Unconsolidated VIE
Total VIE Assets
Maximum Exposure to Loss	7.4	16.3
Total assets	7.4	16.3
Total | Unconsolidated VIE
Total VIE Assets
Maximum Exposure to Loss	124.5	118.9
Total assets	$ 124.5	$ 118.9

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Transactions with related parties (Details) - USD ($)		3 Months Ended		9 Months Ended
	Mar. 27, 2020	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Transactions with related parties
Gross written premiums		$ 356,000,000.0	$ 413,700,000	$ 1,496,200,000	$ 1,523,100,000
Receivables due from affiliates		22,000,000.0		22,000,000.0		$ 16,100,000
Payables due to affiliates		900,000		900,000		$ 900,000
Payments for litigation				2,200,000
Insurance and MGU affiliates, or their subsidiaries
Transactions with related parties
Gross written premiums		$ 16,000,000.0	$ 21,700,000	$ 84,100,000	$ 70,700,000
Holders of series B preference shares | Expense reimbursement
Transactions with related parties
Amount of transaction	$ 250,000
Holders of series B preference shares | Expense reimbursement requiring written consent
Transactions with related parties
Amount of transaction	1,000,000
Holders of series B preference shares | Other professional fees reimbursement
Transactions with related parties
Amount of transaction	$ 500,000

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Commitments and contingencies - Leases (Details) - USD ($) $ in Millions	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019	Dec. 31, 2019
Leases
Operating lease expense	$ 3.0	$ 3.4	$ 9.0	$ 9.3
Operating lease right-of-use assets	27.1		27.1		$ 27.4
Lease liability	$ 29.0		$ 29.0		$ 29.3
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible List]	us-gaap:OtherAssets		us-gaap:OtherAssets		us-gaap:OtherAssets
Operating Lease, Liability, Current, Statement of Financial Position [Extensible List]	us-gaap:OtherLiabilitiesCurrent		us-gaap:OtherLiabilitiesCurrent		us-gaap:OtherLiabilitiesCurrent
Operating Lease, Liability, Noncurrent, Statement of Financial Position [Extensible List]	us-gaap:OtherLiabilitiesNoncurrent		us-gaap:OtherLiabilitiesNoncurrent		us-gaap:OtherLiabilitiesNoncurrent
Leased offices
Leases
Weighted average lease term (years)	7 years		7 years
Leased equipment
Leases
Weighted average lease term (years)	3 years		3 years

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Commitments and contingencies - Lease balances (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Commitments and Contingencies Disclosure [Abstract]
Operating lease right-of-use assets	$ 27.1	$ 27.4
Current lease liabilities	9.2	8.3
Non-current lease liabilities	$ 19.8	$ 21.0
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible List]	us-gaap:OtherAssets	us-gaap:OtherAssets
Operating Lease, Liability, Current, Statement of Financial Position [Extensible List]	us-gaap:OtherLiabilitiesCurrent	us-gaap:OtherLiabilitiesCurrent
Operating Lease, Liability, Noncurrent, Statement of Financial Position [Extensible List]	us-gaap:OtherLiabilitiesNoncurrent	us-gaap:OtherLiabilitiesNoncurrent

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Commitments and contingencies - Weighted average remaining lease term and weighted average discount rate (Details)	Sep. 30, 2020
Leased offices
Property, Plant and Equipment [Line Items]
Weighted average lease term (years)	7 years
Weighted average discount rate	3.30%
Leased equipment
Property, Plant and Equipment [Line Items]
Weighted average lease term (years)	3 years
Weighted average discount rate	3.30%

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Commitments and contingencies - Future annual minimum rental payments (Details) - USD ($) $ in Millions	Sep. 30, 2020	Dec. 31, 2019
Commitments and Contingencies Disclosure [Abstract]
2020	$ 2.4
2021	9.6
2022	9.5
2023	5.7
2024	2.3
2025 and after	1.2
Total future annual minimum rental payments as at June 30, 2020	30.7
Less: present value discount	(1.7)
Lease liability	$ 29.0	$ 29.3