As filed with the Securities and Exchange Commission on June 20, 2023.

Registration No. 333-271270

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Amendment No. 3

to

Form F-1

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

FIDELIS INSURANCE HOLDINGS LIMITED

(Exact Name of Registrant as Specified in its Charter)

Bermuda	6331	Not Applicable
(State or other jurisdiction of incorporation or organization)	(Primary Standard Industrial Classification Code Number)	(I.R.S. Employer Identification Number)

Fidelis Insurance Holdings Limited

Waterloo House,

100 Pitts Bay Road,

Pembroke,

Bermuda, HM08
+1 441 279 2500

(Address, Including Zip Code, and Telephone Number, Including Area Code, of Registrant’s Principal Executive Offices)

Puglisi & Associates

850 Library Avenue, Suite 204

Newark, Delaware 19711

Attention: Mr. Donald J. Puglisi

(Address, Including Zip Code, of Registrant’s agent for service)

Copies to:

Joseph D. Ferraro Jennifer Tait Willkie Farr & Gallagher (UK) LLP Citypoint, 1 Ropemaker Street London EC2Y 9AW United Kingdom Telephone: +44 20 3580 4700 Gary D. Boss Benjamin J. Cohen Kirsten Gaeta Latham & Watkins LLP 1271 Avenue of the Americas New York, New York 10020 Telephone: (212) 906-1200

Approximate date of commencement of proposed sale to the public: As soon as practicable after this registration statement becomes effective.

If any of the securities being registered on this form are to be offered on a delayed or continuous basis pursuant to Rule 415 under the Securities Act of 1933, check the following box  ☐

If this form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering.  ☐

If this form is a post-effective amendment filed pursuant to Rule 462(c) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering.  ☐

If this form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering.  ☐

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 (Do not check if a smaller reporting company)	☒
Smaller reporting company	☐	Emerging growth company	☐

If an emerging growth company that prepares its financial statements in accordance with U.S. GAAP, 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 7(a)(2)(B) of the Securities Act.  ☐

The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933, as amended, or until the registration statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to Section 8(a), may determine.

The information in this preliminary prospectus is not complete and may be changed. The securities may not be sold until the registration statement filed with the Securities and Exchange Commission is declared effective. This preliminary prospectus is not an offer to sell these securities and it is not soliciting an offer to buy these securities in any jurisdiction where the offer or sale of such securities is not permitted.

SUBJECT TO COMPLETION, DATED JUNE 20, 2023

FIDELIS INSURANCE HOLDINGS LIMITED

17,000,000 Common Shares

This is the initial public offering of the common shares, par value $0.01 per share, of Fidelis Insurance Holdings Limited (the “Common Shares”). We are offering 5,714,286 Common Shares. The selling shareholders named under the caption “Principal and Selling Shareholders” below (the “Selling Shareholders”) are offering an additional 11,285,714 Common Shares. We will not receive any of the proceeds from the sale of the Common Shares being sold by the Selling Shareholders in this offering.

Currently, no public market exists for our Common Shares. We have applied to list our Common Shares on the New York Stock Exchange (“NYSE”) under the symbol “FIHL.”

We anticipate that the initial public offering price for our Common Shares will be between $16.00 and $19.00 per Common Share.

Investing in our Common Shares involves risks. See “Risk Factors” beginning on page 33. Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or passed upon the adequacy or accuracy of this prospectus. Any representation to the contrary is a criminal offense.

	Per Common Share	Total
Initial public offering price	$	$
Underwriting discounts and commissions(1)	$	$
Proceeds, before expenses, to Fidelis Insurance Holdings Limited	$	$
Proceeds, before expenses, to the Selling Shareholders	$	$

(1) Please see “Underwriting” for a description of compensation payable to the underwriters.

The underwriters also may purchase up to 2,550,000 additional Common Shares from the Selling Shareholders at the initial public offering price less the underwriting discounts and commissions, within 30 days from the date of this prospectus.

The underwriters expect to deliver the Common Shares to purchasers on or about                 , 2023.

J.P. Morgan Barclays Jefferies

BMO Capital Markets Citigroup UBS Investment Bank

Dowling & Partners Securities, LLC

Prospectus dated                 , 2023

TABLE OF CONTENTS

	Page
About This Prospectus		1
Summary		5
Summary Financial and Operating Data		26
Risk Factors		33
Use of Proceeds		92
Dividend Policy		93
Capitalization		94
Dilution		95
Cautionary Note Regarding Forward-Looking Statements		97
The Separation Transactions		99
Unaudited Pro Forma Condensed Combined Financial Information		102
Management’s Discussion and Analysis of Financial Condition and Results of Operations		111
Business		159
Management and Corporate Governance		182
Executive Compensation		191
Principal and Selling Shareholders		197
Material Contracts and Related Party Transactions		200
Description of Share Capital		217
Comparison of Shareholder Rights		226
Shares Eligible for Future Sale		234
Certain Regulatory Considerations		237
Certain Tax Considerations		251
Underwriting		264
Legal Matters		274
Experts		275
Where Prospective Investors Can Find Additional Information		276
Glossary of Selected Terms		277
Index to the Consolidated Financial Statements		F-1

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ABOUT THIS PROSPECTUS

We and the Selling Shareholders have not authorized anyone to provide any information different from that contained in this prospectus or in any free writing prospectuses prepared by us or on our behalf or to which we have referred prospective investors. We and the Selling Shareholders take no responsibility for, and can provide no assurance as to the reliability of, any other information that others may give prospective investors. This prospectus is an offer to sell only the shares offered hereby, but only under circumstances and in jurisdictions where it is lawful to do so. The information contained in this prospectus is accurate only at the date on the front cover of this prospectus, regardless of the time of delivery of this prospectus or any sale of our Common Shares.

We further note that the representations, warranties and covenants made by us in any agreement that is filed as an exhibit to the registration statement of which this prospectus is a part were made solely for the benefit of the parties to such agreement, including, in some cases, for the purpose of allocating risk among the parties to such agreement, and should not be deemed to be a representation, warranty or covenant made to prospective investors or for the benefit of prospective investors. Moreover, such representations, warranties or covenants were accurate only at the date they were made. Accordingly, such representations, warranties and covenants should not be relied on as accurately representing the current state of our affairs.

Except as otherwise indicated, the information in this prospectus assumes the effectiveness of our Amended and Restated Bye-Laws (as defined herein) and the consummation of (i) a number of separation and reorganization transactions, which were completed on January 3, 2023, in order to create two distinct holding companies and businesses: FIHL (as the issuer of the Common Shares sold by the Selling Shareholders in this offering) and Shelf Holdco II Limited (“MGU HoldCo”) (the “Separation Transactions”) and (ii) this offering.

Certain Defined Terms

Certain abbreviations and definitions of certain insurance, reinsurance, financial and other terms used in this prospectus are defined in the “Glossary of Selected Terms” section of this prospectus.

Exchange Control

We intend to apply for and expect to receive consent under the Exchange Control Act 1972 (and its related regulations) from the Bermuda Monetary Authority (the “BMA”) for the issue and transfer of the Common Shares to and between non-residents of Bermuda for exchange control purposes provided the Common Shares remain listed on an appointed stock exchange, which includes NYSE. In granting such consent, neither the BMA nor any other relevant Bermuda authority or government body accepts any responsibility for our financial soundness or the correctness of any of the statements made or opinions expressed in this prospectus.

Service of Process and Enforcement of Civil Liabilities

We are a Bermuda exempted company. As a result, the rights of holders of our Common Shares will be governed by Bermuda law and our memorandum of association and the Amended and Restated Bye-Laws. The rights of shareholders under Bermuda law may differ from the rights of shareholders of companies incorporated in other jurisdictions. Some of our directors and officers are not residents of the United States, and a substantial portion of our assets are located outside the United States. As a result, it may be difficult for investors to effect service of process on those persons in the United States or to enforce in the United States judgments obtained in U.S. courts against us or those persons based on the civil liability provisions of the U.S. securities laws. It is doubtful whether courts in Bermuda will enforce judgments obtained in other jurisdictions, including the United States, against us or our directors or officers under the securities laws of those jurisdictions or entertain actions in Bermuda against us or our directors or officers under the securities laws of other jurisdictions.

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Investors Outside the United States

Neither we nor any of the Selling Shareholders have done anything that would permit the possession or distribution of this prospectus in any jurisdiction where action for that purpose is required, other than in the United States. Persons outside the United States who come into possession of this prospectus must inform themselves about, and observe any restrictions relating to, the offering of our Common Shares and the distribution of this prospectus outside of the United States.

REGISTERED TRADEMARKS AND TRADEMARK APPLICATIONS

We own or have rights to use trademarks, service marks or trade names that we use in connection with the operation of our business. Other trademarks, service marks and trade names appearing in this prospectus are the property of their respective owners. Solely for convenience, the trademarks, service marks, trade names and copyrights referred to in this prospectus are listed without the ^©, ^® and ^™ symbols, but we will assert, to the fullest extent under applicable law, our rights or the rights of the applicable licensors to these trademarks, service marks, trade names and copyrights.

MARKET AND INDUSTRY DATA AND FORECASTS

Certain market and industry data and forecasts included in this prospectus were obtained from independent market research, industry publications and surveys, governmental agencies and publicly available information. Industry surveys, publications and forecasts generally state that the information contained therein has been obtained from sources believed to be reliable, but that the accuracy and completeness of such information is not guaranteed. We have not independently verified any of the data from third-party sources, nor have we ascertained the underlying assumptions relied upon therein. Similarly, independent market research and industry forecasts, which we believe to be reliable based upon our management’s knowledge of the industry, have not been independently verified. While we are not aware of any material misstatements regarding the market or industry data presented herein, our estimates involve risks and uncertainties and are subject to change based on various factors, including those discussed under the heading “Risk Factors.”

BASIS OF PRESENTATION

Presentation of Financial Information

References to “Previous Fidelis” refer to Fidelis Insurance Holdings Limited (“FIHL”) and its consolidated subsidiaries prior to the consummation of the Separation Transactions and this offering. References to “Current Fidelis” refer to FIHL and its consolidated subsidiaries following the consummation of the Separation Transactions. Unless otherwise indicated, or the context otherwise requires, references herein to “Fidelis,” “Group,” “we,” “our,” “us,” and other similar references refer (i) prior to the consummation of the Separation Transactions and this offering to Previous Fidelis and (ii) following the consummation of the Separation Transactions to Current Fidelis. Unless otherwise stated or the context otherwise requires, all information in this prospectus reflects the consummation of the Separation Transactions and the completion of this offering. References to “segment(s)” and “pillar(s)” shall have the same meaning as used herein and shall be used interchangeably to refer to each of the three pillars or segments of our business, Bespoke, Specialty and Reinsurance.

See “Summary—The Separation Transactions,” “Summary—Our Corporate Structure” and “The Separation Transactions” for a more particularized description of the Separation Transactions.

The financial information included herein has been derived from the financial statements and accounting records of Fidelis and has been prepared in accordance with generally accepted accounting principles in the

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United States (“U.S. GAAP”). Following this offering, FIHL will operate and control all of the business and affairs and consolidate the financial results of FIHL and its consolidated subsidiaries. Amounts in this prospectus and the financial statements included in this prospectus are presented in U.S. dollars rounded to the nearest million, unless otherwise noted. Certain amounts presented in tables are subject to rounding adjustments and, as a result, the totals in such tables may not sum.

The financial information included herein contains the following measures, which we use to assess the financial performance of our business:

Premiums Written

• Gross premiums written (“GPW”) means total premiums received; and

• Net premiums written (“NPW”) means GPW less reinsurance premiums ceded.

Premiums written are recorded on inception of the policy. Premiums written include estimates based on information received from insureds, brokers and cedants, and any subsequent differences arising on such estimates are recorded as premiums written in the period in which they are determined.

Earned and Unearned Premiums

Premiums written are earned on a basis consistent with risks covered over the period the coverage is provided. Net premiums written, when earned, are referred to herein as net premiums earned (“NPE”).

The portion of the premiums written applicable to the unexpired terms of the underlying contracts and policies are recorded as unearned premium (“UPR”).

Non-U.S. GAAP Financial Measures

Our financial statements included in this prospectus have been prepared in accordance with U.S. GAAP. We have included certain non-U.S. GAAP financial measures in this prospectus, as further described below, that may not be directly comparable to other similarly titled measures used by other companies and therefore may not be comparable among companies. For purposes of Regulation G and Section 10(e) of Regulation S-K, a non-U.S. GAAP financial measure is a numerical measure of a company’s historical or future financial performance, financial position or cash flows that excludes amounts, or is subject to adjustments that have the effect of excluding amounts, that are included in the most directly comparable measure calculated and presented in accordance with U.S. GAAP in the statements of operations, balance sheets, or statement of cash flows of the company; or includes amounts, or is subject to adjustments that have the effect of including amounts, that are excluded from most directly comparable measure so calculated and presented. Pursuant to the requirements of Regulation G and Section 10(e) of Regulation S-K, we have provided reconciliations of non-U.S. GAAP financial measures to the most directly comparable U.S. GAAP financial measures. These non-U.S. GAAP measures are provided because our management uses these financial measures in monitoring and evaluating our ongoing results and trends.

This prospectus contains “non-U.S. GAAP financial measures,” including accident year loss ratio excluding catastrophes, large losses and prior year reserve movements, operating net income, and operating return on equity (“Operating RoE”), which are financial measures that are not required by, or presented in accordance with U.S. GAAP. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations— Performance Measures and Non-U.S. GAAP Financial Measures” for an explanation and reconciliations.

We believe that, in addition to our results determined in accordance with U.S. GAAP (that include performance measures such as ratio of losses and loss adjustment expenses to NPE (“loss ratio”), underwriting

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ratio, expense ratio, Fidelis MGU commissions ratio, policy acquisition expense ratio, general and administrative expense ratio, combined ratio, net investment return, total investment return, total investment return percentage and return on equity (“RoE”), certain non-U.S. GAAP measures, including accident year loss ratio excluding catastrophes, large losses and prior year reserve movements, operating net income, and Operating RoE are useful in evaluating our business and the underlying trends that are affecting our performance. Such non-U.S. GAAP measures are primary indicators that our management uses internally to conduct and measure its business and evaluate the performance of its consolidated operations. Our management believes these non-U.S. GAAP financial measures are useful as they provide meaningful analysis of the performance of the business. These non-U.S. GAAP financial measures are used in addition to and in conjunction with results presented in accordance with U.S. GAAP. These non-U.S. GAAP financial measures reflect an additional way of viewing aspects of our operations that, when viewed with our U.S. GAAP results and, where applicable, the accompanying reconciliations to corresponding U.S. GAAP financial measures, provide a more complete understanding of factors and trends affecting our business. A material limitation associated with these non-U.S. GAAP measures compared to the U.S. GAAP measures is that they may not be comparable to other companies with similarly titled items that present related measures differently. The non-U.S. GAAP measures should be considered as a supplement to, and not as a substitute for or superior to, the corresponding measures calculated in accordance with U.S. GAAP.

See “Management’s Discussion and Analysis of Financial Condition and Results of Operations” for a reconciliation of these non-U.S. GAAP financial measures to the most directly comparable financial measures stated in accordance with U.S. GAAP.

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SUMMARY

This summary highlights information contained elsewhere in this prospectus. Because this is only a summary, it does not contain all of the information that you should consider before investing in Common Shares and it is qualified in its entirety by, and should be read in conjunction with, the more detailed information appearing elsewhere in this prospectus. You should read the entire prospectus carefully, including “Risk Factors,” “Cautionary Note Regarding Forward-Looking Statements,” and our financial statements and the related notes included elsewhere in this prospectus, before deciding to purchase Common Shares. Unless otherwise indicated, or the context otherwise requires, references herein to “Fidelis,” “Group,” “we,” “our,” “us,” and other similar references refer (i) prior to the consummation of the Separation Transactions and this offering to Previous Fidelis and (ii) following the consummation of the Separation Transactions to Current Fidelis.

Certain abbreviations and definitions of certain insurance, reinsurance, financial and other terms used in this prospectus are defined in the “Glossary of Selected Terms” section of this prospectus.

Our History; Then to Now

Fidelis is a global (re)insurance company, with operations in Bermuda, Ireland and the United Kingdom. FIHL was formed in Bermuda in 2014 by Richard Brindle, under the principles of focused, process-driven and disciplined underwriting and risk selection, strong client and broker relationships and nimble capital deployment. Fidelis completed its initial funding and began underwriting business in June 2015 under the direction of an experienced management team led by Richard Brindle. Since then, Fidelis has assembled a diversified global book of (re)insurance business and achieved scale as a specialty (re)insurer with GPW of $3.0 billion, total revenues of $1.5 billion and net income of $62.3 million for the year ended December 31, 2022. Our growth has continued in 2023, with our GPW increasing to $1.2 billion in the three months ended March 31, 2023 compared to $1.0 billion for the three months ended March 31, 2022.

On January 3, 2023, the Separation Transactions were completed and two distinct holding companies and businesses were created: FIHL and MGU HoldCo. FIHL is the parent holding company for Current Fidelis, is the issuer of the Common Shares sold by the Selling Shareholders in this offering and continues to own all of the insurance operating subsidiaries of Current Fidelis, comprised of Fidelis Insurance Bermuda Limited (“FIBL”), Fidelis Underwriting Limited (“FUL”) and Fidelis Insurance Ireland DAC (“FIID”). Current Fidelis also has its own service company, FIHL (UK) Services Limited, with a branch in Ireland (“FIHL (UK) Services”).

MGU HoldCo is the parent holding company for the managing general underwriting platform (the “Fidelis MGU”) that carries on the origination and underwriting activities on behalf of Current Fidelis and is led by Mr. Brindle. MGU HoldCo’s principal operating subsidiaries are Pine Walk Capital Limited (“Pine Walk Capital”), Pine Walk Europe SRL (“Pine Walk Europe”) and Shelf Opco Bermuda Limited, a newly incorporated MGU in Bermuda (“Bermuda MGU”). The underwriting activities of each of the licensed insurance carriers of Current Fidelis (FIBL, FUL and FIID) are outsourced to the corresponding operating subsidiaries of Fidelis MGU on a jurisdictional basis (Bermuda MGU, Pine Walk Capital and Pine Walk Europe, respectively). Each of the operating subsidiaries of Fidelis MGU has delegated underwriting authority to source and bind contracts for and on behalf of each of FIBL, FUL and FIID, respectively. See “Material Contracts and Related Party Transactions—Framework Agreement.” MGU HoldCo and its subsidiaries will not be consolidated with FIHL and its subsidiaries.

On December 20, 2022, FIHL and MGU HoldCo entered into a rolling 10-year framework agreement (the “Framework Agreement”) that governs the ongoing relationship between the two groups of companies (see “—Our Corporate Structure” for additional details). Following the consummation of the Separation Transactions

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on January 3, 2023, Mr. Brindle’s employment agreement and the employment agreements of certain other senior management and other employees of Previous Fidelis remained with Fidelis Marketing Limited (“FML”) (the service company which transferred to and became part of Fidelis MGU as part of the Separation Transactions), and Mr. Brindle is now the Chairman and Chief Executive Officer of Fidelis MGU. See “The Separation Transactions.”

The Separation Transactions allow FIHL to access the underwriting expertise of Fidelis MGU while allowing Fidelis MGU to attract and retain highly sophisticated underwriting talent, including Mr. Brindle and senior underwriters. We believe that the Separation Transactions and the Framework Agreement have structural benefits for both groups of companies, including increased flexibility to quickly respond to evolving insurance and reinsurance market conditions and to help sustain our strong underwriting results through access to top talent. Our objective following the completion of the Separation Transactions remains to further solidify Fidelis’ position as a leading bespoke, specialty and property underwriter.

Prior to the Separation Transactions, the Group was assigned an “A” (Excellent) financial strength rating by A.M. Best Company, Inc. (“A.M. Best”), the third-highest of 13 rating levels, with a stable outlook on all entities. A.M. Best’s ratings range from “A+” to “D.” Each A.M. Best rating category from “A+” to “C” may be designated either an additional plus (+) or a minus (-) sign as a rating notch that reflects a gradation of financial strength within the rating category. Additionally, A.M. Best assigned a “BBB” long-term issuer credit rating to FIHL, which indicates a good ability to meet ongoing senior financial obligations and a financial strength rating of “A” (Excellent) and the long-term issuer credit rating of “A” (Excellent) to FIBL, FUL and FIID. In connection with the Separation Transactions, the Group completed a rating evaluation service with A.M. Best, following which, A.M. Best had placed “under review with negative implications” the ratings assigned to FIHL, including the Group’s financial strength rating of “A.” On February 3, 2023, A.M. Best removed from “under review with negative implications” and affirmed the financial strength rating of “A” (Excellent) and the long-term issuer credit rating of “A” (Excellent) of FIBL, FUL and FIID. In addition, A.M. Best removed from “under review with negative implications” and affirmed the long-term issuer credit rating of “BBB” (Good) of FIHL. The outlook assigned to these ratings remained negative at such date. The negative outlooks acknowledge that A.M. Best has noted that it will continue to monitor the Group’s market presence as well as subsequent operating performance now that the Separation Transactions have been consummated.

Prior to the Separation Transactions, the Group was assigned an “A-” financial strength rating by S&P Global Ratings (“S&P”), with a positive outlook, which indicates strong capacity to meet financial commitments but somewhat more susceptibility to the adverse effects of changes in circumstances and economic conditions than those in higher-rated categories. S&P’s ratings range from “AAA” to “D.” Each S&P rating category from “AA” to “CCC” may be modified by the addition of a plus (+) or minus (-) sign to show relative standing within the rating categories. Additionally, S&P has assigned a “BBB” long term issuer rating to FIHL, which indicates adequate capacity to meet financial commitments but greater susceptibility to adverse economic conditions. In connection with the Separation Transactions, the Group completed a rating evaluation service with S&P, following which, S&P had placed under review the ratings assigned to FIHL, including the Group’s financial strength rating of “A-.” On August 5, 2022, S&P affirmed the Group’s ratings, including the “A-” financial strength rating assigned to the Group and a “BBB” long term issuer rating to FIHL, but revised its outlook from positive to stable for all entities. Despite the revision, S&P expressed confidence in the Group’s future operating earnings and strong capital position, noting in particular the Group’s underwriting outperformance of peers between 2017 and 2022.

Following the announcement of the Separation Transactions, on August 1, 2022, Moody’s Investors Service (“Moody’s”) assigned a “Baa2” long-term issuer rating to FIHL and “A3” insurance financial strength ratings to FIBL, FUL and FIID. The outlook for FIHL is stable. Moody’s generic rating classifications range from “Aaa” to “C.” Each Moody’s generic rating classification from “Aa” to “Caa” may be modified to append numerical modifiers 1, 2, or 3 to show relative position within the rating categories.

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Our Company

Fidelis is a leading global provider of bespoke and specialty insurance and reinsurance products. We believe our differentiated underwriting positions us well to generate strong returns across (re)insurance cycles. Current Fidelis is led by Mr. Daniel Burrows who has more than 35 years of experience in the insurance industry and is supported by a highly experienced management team that manages the operations of Current Fidelis based on our founding principles.

Following the Separation Transactions, Current Fidelis is positioned as a global, specialty insurance provider with exclusive right of first access to Fidelis MGU’s underwriting business during the term of the Framework Agreement. Based on Fidelis’ historical experience, we expect this long-term partnership to deliver strong returns to our shareholders, primarily driven by our underwriting results. We aim to be good stewards of capital by effectively balancing capital deployment across market opportunities with capital distributions to our shareholders.

We will continue to benefit from decades of thought and process leadership and innovation through our strategic relationship with Fidelis MGU. The management team of Fidelis MGU, led by Mr. Brindle, has a robust track record built across multiple platforms. Mr. Brindle has more than 38 years of underwriting leadership, including founding Lancashire Holdings Limited (“Lancashire”) and holding leading roles at Syndicates 488 and 2488 at Lloyd’s of London (“Lloyd’s”). Teams led by Mr. Brindle oversaw Lancashire stock price appreciation of 412.0% from December 16, 2005 (the date of Lancashire’s initial public offering) to December 31, 2013 (immediately prior to his retirement from Lancashire), significantly exceeding the 71.0% price appreciation from a group of Lancashire’s publicly traded insurance company peers for the period (including Ace, XL, Arch, Everest, PartnerRe, Axis, Allied World, RenaissanceRe, Validus, Montpelier, Greenlight Re, Third Point Re, Hiscox, Amlin, Catlin, Beazley and Novae). Past performance of Lancashire is no guarantee of future results for Fidelis. Mr. Brindle and his team also outperformed at Lloyd’s by delivering a 17.5% return on a straight average for Syndicates 488 and 2488 during his time there from 1986 to 1998, compared to Lloyd’s average return of 0.9% over the same period. Past performance of Syndicates 488 and 2488 is no guarantee of future results for Fidelis. Further, while at Fidelis, between 2017 and 2022 Mr. Brindle and his management team achieved strong, consistent underwriting performance with an average loss ratio of 45.3%, an average combined ratio of 85.8% and an average standard deviation of combined ratio of 6.5% compared with the peer average of 64.3% and 99.5% and 8.1%, respectively. Over this same period, Fidelis’ average loss ratios for each of its Specialty, Bespoke and Reinsurance pillars was 42.8%, 26.7% and 64.9%, respectively, compared to its peers’ average loss ratios of 61.4%, 61.4% and 72.1%, respectively. Fidelis’ combined ratio was 86.0%, 76.3%, 86.6%, 80.6%, 92.9% and 92.1% in 2017, 2018, 2019, 2020, 2021 and 2022, respectively, compared to a peer average combined ratio of 109.4%, 96.9%, 96.7%, 103.7%, 96.6% and 93.5% in 2017, 2018, 2019, 2020, 2021 and 2022, respectively. In the three months ended March 31, 2023, our loss ratio was 41.3% and combined ratio was 79.1% compared with a peer average of 59.3% and 90.5%, respectively. Fidelis’ peer group includes Arch, Argo, Aspen, Markel, W. R. Berkley, Hiscox, Beazley, Lancashire, Everest Re, Axis Capital and RenaissanceRe (except for the three months ended March 31, 2023 which excludes Aspen, Hiscox, Beazley and Lancashire as the information is not available for this period). In each case, prior underwriting and combined ratio performance is no guarantee of future performance. Each of the Fidelis and financial peer combined ratios is calculated as the sum of losses and loss adjustment expenses, policy acquisition expenses and general and administrative expenses as a percentage of NPE in all periods except 2018. In 2018, the Fidelis combined ratio included a negative $2.1 million adjustment to NPE as a result of the costs to acquire a derivative instrument to protect against Typhoon Jebi losses and a $10 million positive adjustment to investment returns recognized on the derivative. Financial peer combined ratios were calculated as the average of the reported combined ratios of each company.

We will continue to focus on nimble underwriting designed to capitalize on current market trends and dislocations as well as emerging risk solutions. We expect to maintain at a minimum the existing underwriting

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standards and where appropriate will look for enhancements. The team of underwriters at Fidelis MGU continues to maintain the robust processes and use of technology that have been key to Fidelis’ historical success at ensuring its underwriting efforts capture recent market developments. We believe this close coordination reduces the likelihood of siloed underwriting and gives us a competitive advantage in our underwriting, risk assessment and ability to offer as many products as possible to clients. A crucial and distinguishing part of those robust processes is daily Underwriting and Marketing Conference Calls (the “UMCC”) with practice leads and key members of senior management (including risk modeling, actuarial, legal, compliance, contract wordings and claims representatives) to provide live market insights and multiple perspectives to allow underwriters to quickly assess emerging opportunities, achieve strong underwriting and cross-sell across our product range. See “—Our Competitive Strengths” below for further detail.

Since we began underwriting business in 2015, Fidelis has reached an attractive scale in bespoke and specialty insurance and property reinsurance markets while delivering robust results. Our GPW grew from $0.5 billion for the year ended December 31, 2017 to $3.0 billion for the year ended December 31, 2022, a compound annual growth rate of 40.6%, while delivering an average loss ratio of 45.3% and an average combined ratio of 85.8%. Over the same period, our NPE grew from $0.2 billion for the year ended December 31, 2017 to $1.5 billion for the year ended December 31, 2022, a compound annual growth rate of 47.0%. Our GPW continued to grow to $1.2 billion for the three months ended March 31, 2023 compared to $1.0 billion for the three months ended March 31, 2022. Our loss ratio and combined ratio for the three months ended March 31, 2023 were 41.3% and 79.1%, respectively. In addition to earnings growth from the origination of new business, we believe that there is significant embedded earnings potential in previously written business due to the requirements of applicable accounting rules that revenue from written premiums must be recognized when earned over the life of a policy. This is reflected in our gross UPR balance of $3.3 billion at March 31, 2023.

Our scale and access to the highly selective underwriting capabilities of Fidelis MGU via our strategic relationship will allow us to capitalize on current insurance market trends and continue focusing on delivering growth coupled with strong underwriting results.

Fidelis is subject to varying degrees of regulation and supervision in the jurisdictions in which it operates. In particular, the businesses of our three insurance operating subsidiaries, FIBL, FUL and FIID, are authorized by, and subject to insurance laws and regulations that are administered and enforced by, a number of different governmental and non-governmental self-regulatory authorities and associations in each of their respective jurisdictions and internationally. For a summary of the regulatory environment of our insurance operating subsidiaries, primarily in their respective jurisdictions of Bermuda, U.K. and Ireland, see “Certain Regulatory Considerations.”

Our Commitment to Environmental, Social and Governance Matters

Fidelis is committed to being a leader in the industry with respect to standards for environmental, social and governance (“ESG”) matters. We are currently committed to transitioning our insurance portfolios to net-zero greenhouse gas emissions by 2050. To work towards this, to the extent possible, we are developing tools to measure the insurance-associated emissions of our insurance portfolios. We have carried out a joint study on approximately $8.2 billion of premiums and 28,500 policies spanning between 2012 and 2021, which demonstrated that higher third-party ESG ratings were generally correlated with lower loss ratios. Fidelis aims to embed ESG factors in its underwriting processes where appropriate. In addition, Fidelis has certain existing underwriting restrictions. These underwriting restrictions include not directly insuring thermal coal (including dedicated infrastructure projects such as ports and railways), tar sand extraction, Arctic oil and gas exploration and drilling and fracking operations. Fidelis will also not provide cover to companies whose revenues from the above-mentioned activities account for more than 20% of their total revenues. Fidelis has been for some time seeking to use policy language to minimize exposure to forced labor and modern slavery in particular in our marine cargo line of business.

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Furthermore, FIHL’s core fixed income investment portfolio (which represents 98.4% of invested assets) is managed in a manner that is consistent with Fidelis’ sustainability principles and ESG objectives. This includes a requirement that a minimum of 3% of the core fixed income portfolio’s total assets under management must be invested in “green, social and sustainable” (“GSS”) bonds, as classified by Bloomberg pursuant to its proprietary GSS Indices. The GSS Indices utilize the Bloomberg Global Aggregate Index, the Bloomberg Sustainable Finance Group’s green, social and sustainability bond indicators and fields that show alignment with the International Capital Market Association Green Bond, Social Bond and Sustainability Bond Principles and Guidelines. At March 31, 2023, 3.9% of Fidelis’ core fixed income portfolio was invested in GSS bonds. Furthermore, the investment portfolio includes restrictions against holding securities of issuers that have a ‘poor’ MSCI Inc. (“MSCI”) ESG rating (with a rating below ‘B’ or issuers that currently have a ‘red’ MSCI controversy flag). Securities of these issuers may only be held if the investment manager demonstrates and documents in writing pursuant to company policies a positive forward-looking ESG view of the issuer. Fidelis has also adopted negative screens to limit exposure to certain industries and activities in its investment portfolio. These include screens against holding securities of any issuers involved in thermal coal, oil and gas (though an issuer may derive up to 20% of its annual revenues from oil and gas) or arms (certain types of arms are completely excluded, others such as firearm sales are permitted to comprise up to 10% of annual revenues), and restrictions against those that fail animal welfare and for-profit prisons screens. As a result of such negative screens, Fidelis was able to limit the core fixed income portfolio’s direct exposure to the securities of companies deriving revenues from fossil fuels to only three companies, which at March 31, 2023 comprised 0.4% of Fidelis’ core fixed income portfolio. Furthermore, currently Fidelis has no direct exposure in its investment portfolio to energy companies and its exposure to corporate securities identified as “utilities” comprises 0.6% of the core fixed income portfolio.

Additionally, we have taken action in each year since 2018 to more than offset our operational carbon emissions and we are committed to continuing to do so going forward. In 2018, 2019, 2020, 2021 and 2022, we offset our carbon emissions at 125%, 150%, 200%, 150% and 110%, respectively, on a tons-of-carbon-equivalent basis through the use of carbon credits. We partner with relevant industry specialists to calculate our carbon emissions.

We were awarded carbon credits through investments in Earth’s forests, including forest protection in investments in the April Salumei area of Papua New Guinea in 2018 and 2019 and reforestation projects in Nicaragua and Tanzania in conjunction with CommuniTree and Hazda Hunter Gatherers, respectively, in 2020, 2021 and 2022.

Diversity, equity and inclusion are integral to Fidelis. We pursue a diversity, equity and inclusion strategy that includes accountability, representation, advancement, culture, outreach and fostering a sense of belonging for all our employees. We employ targeted recruiting strategies to identify diverse candidates and partner with external agencies to advertise vacancies with the goal of increasing the hiring of women and ethnically diverse employees. Where available, we monitor certain diversity, equity and inclusion statistics (gender, ethnicity, age, marital status, religion, caring responsibilities and disability, each as provided by candidates on a voluntary basis) both at the outreach/interview stage and for our employee population so that we can see progress with respect to the diverse candidate pools. Comparative data on diverse candidate sourcing available to us demonstrates an improved diversity mix of approximately 1% across gender and approximately 6.5% across ethnicity from December 31, 2021 to February 1, 2023 (being the latest practicable date), acknowledging that the number of employees following the consummation of the Separation Transactions has been reduced due to staff transfers to Fidelis MGU. In addition, we seek to promote our diverse talent from within, identifying those that have potential to take on more senior roles and fast-tracking them through exposure to a wide range of business opportunities as well as structured training and development.

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Strategic Relationship with Fidelis MGU

We believe the insurance industry is evolving rapidly and is primed for further value chain disaggregation which will allow specialist underwriters to benefit from access to clients and risks and to provide access to alternate forms of capital.

Following the consummation of the Separation Transactions, MGU HoldCo became a minority investor in FIHL (holding 9.9% of the Common Shares) and entered into the Framework Agreement with FIHL to build a long-term agency relationship that provides strong economic and strategic alignment between the two groups of companies.

The Framework Agreement, under which Current Fidelis secures business from Fidelis MGU, has a rolling initial term of 10 years. Years one to three will roll automatically (each year resetting the term of the Framework Agreement to a new 10-year period) and the notice to roll will be deemed given at the end of years one, two and three (i.e., the years roll automatically and will not be subject to any underwriting target or preconditions to rolling). From year four onwards, the Framework Agreement will roll at the sole written election of FIHL, with such election to be delivered at least 90 days prior to the commencement of the subsequent contract year. Any decision by FIHL to elect not to roll the Framework Agreement on or after year four will mean that the remainder of the 10-year term then in effect will continue in place (i.e., the Framework Agreement will have a further nine years to run in the first year following the election by FIHL not to roll the Framework Agreement). See “Material Contracts and Related Party Transactions—Framework Agreement.”

Fidelis MGU manages underwriting, origination, outwards reinsurance, actuarial and claims services with close review and oversight from Current Fidelis to ensure adherence with the agreed upon group-level annual plan (the “Group Annual Plan”), which sets out our underwriting parameters and risk tolerances in respect of our three-pillar underwriting strategy on a gross / net basis for each annual period. While the Framework Agreement establishes the overarching parameters of the outsourced underwriting relationship between Current Fidelis and Fidelis MGU, the relationship is more specifically governed on a jurisdictional basis by a series of Delegated Underwriting Authority Agreements (as defined herein). The parties to each Delegated Underwriting Authority Agreement will prepare their own subsidiary-level annual plans (each, a “Subsidiary Annual Plan”). See “Material Contracts and Related Party Transactions—Framework Agreement—Subsidiary Annual Plans.” Fidelis MGU provides us with a number of enterprise and support services on a cost-plus basis, such as accounting, other finance and reporting services, IT infrastructure, maintenance and system development services and facilities management services pursuant to the services agreement between FIHL and MGU HoldCo relating to the outsourcing of certain non-underwriting services provided by Fidelis MGU to FIHL and FIHL (UK) Services (the “Inter-Group Services Agreement”). See “Material Contracts and Related Party Transactions—Inter-Group Services Agreement.”

We will continue to leverage Fidelis MGU’s sophisticated underwriting technology and talent and will benefit from our shared history in underwriting principles, strategic visions, and managerial approaches. Our arrangement is governed by arm’s-length terms for origination and management consistent with industry commission levels, including market overrider commissions, and with a focus on aligning incentives for strong underwriting performance. Ceding commissions payable to Fidelis MGU will be charged for underwriting, claims and actuarial pricing services and will be calculated based on NPW to ensure alignment on reinsurance purchasing. To avoid fee duplication, ceding commissions payable for open market business sourced by Fidelis MGU are set at 11.5% and ceding commissions payable for business sourced by Fidelis MGU via third-party managing general underwriters to whom underwriting authority has been sub-delegated by Fidelis MGU are set at 3.0%. Business that continues to be sourced by subsidiary cells of Pine Walk Capital will continue to follow the fees and commissions set under those agreements. For the year ended December 31, 2022, the fees and commissions attributable to subsidiary cells of Pine Walk Capital were 10.0% on average of the total Pine Walk Capital GPW. Long-term objectives will be

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further aligned by FIHL paying an ongoing portfolio management fee of 3.0% (“Portfolio Management Fee”) to Fidelis MGU and a 20.0% profit commission on Operating RoE (“Binder Operating RoE”) above a hurdle rate of 5.0% calculated on an aggregate basis for Current Fidelis. Binder Operating RoE is defined in the Framework Agreement as FIHL’s consolidated net underwriting margin (disregarding any business not underwritten by Fidelis MGU following the date of the Framework Agreement and the effect of any FIHL Procured Outwards Reinsurance, as defined in the Framework Agreement) plus all overriders retained by Current Fidelis (disregarding the effect of any FIHL Procured Outwards Reinsurance), minus an Administrative Expenses Allowance (defined in the Framework Agreement as a sum equating to 2.3% of net premiums written), minus the proportion of FIHL’s costs of financing its debt and preference securities included in FIHL’s total capital that is deemed to be allocated to Fidelis MGU, minus the total accumulated ceding commission that is payable by Current Fidelis to Fidelis MGU, minus the Portfolio Management Fee relating to business underwritten by Fidelis MGU, divided by the proportion of FIHL’s opening common shareholders’ equity adjusted for dividend and equity raises (as set out in year-end consolidated audited accounts) that is deemed to be allocated to Fidelis MGU. The calculation of such profit commission will include a deficit carry-forward mechanism for a maximum of three years in which the Binder Operating RoE is below zero. For a more detailed discussion of the fees and commissions payable by Current Fidelis in connection with its outsourced relationship with Fidelis MGU, see “Material Contracts and Related Party Transactions—Framework Agreement—Fees and Commissions.”

We believe the recently completed Separation Transactions make us a scaled property, bespoke and specialty (re)insurer with long-term access to a sophisticated underwriting team focused distinctively on portfolio optimization and insurance portfolio management. Under this structure, we believe we are well positioned to generate attractive returns, deploy capital toward profitable underwriting opportunities sourced through our strategic arrangement with Fidelis MGU, and grow our business. The strategic arrangement adheres to our long-standing philosophy of writing insurance and reinsurance in areas where deep expertise is required to deliver an attractive risk / reward profile through (re)insurance cycles.

The shareholders agreement entered into by current shareholders who own shares in FIHL following the consummation of the Separation Transactions (the “Existing Common Shareholders Agreement”) will be amended and restated (the “Amended and Restated Common Shareholders Agreement”) effective as of the pricing of this offering. The Amended and Restated Common Shareholders Agreement will retain a number of rights granted to MGU HoldCo or other Founders (as defined below) under the Existing Common Shareholders Agreement, such as certain consent rights, minority shareholder protections and board nomination rights. Under the terms of the Amended and Restated Common Shareholders Agreement, for so long as MGU HoldCo beneficially owns at least 4.9% of the Common Shares, the consent of MGU HoldCo will be required for FIHL to undertake certain actions, including effecting any change in the jurisdiction, incorporation or name of FIHL or any member of Current Fidelis, making a material change to the nature or scope of the business underwritten by FIHL and any member of Current Fidelis, effecting any amendments to its constitutional documents that are reasonably likely to have a material adverse effect on Fidelis MGU and making certain acquisitions or dispositions of assets. MGU HoldCo will also enjoy certain subscription and allocation rights in respect of further Common Share issuances or sales. MGU HoldCo will be subject to a prohibition on the sale of its Common Shares provided that the Framework Agreement is in effect. This prohibition shall not apply in the event of a Common Share buyback or other transactions undertaken by FIHL in response to certain adverse regulatory or accounting effects on MGU HoldCo. Additionally, MGU HoldCo will be entitled to nominate one individual to serve as a director on the board of directors of FIHL (the “Board”), for so long as MGU HoldCo together with its Shareholder Affiliate Transferees beneficially own at least 50% of the Common Shares initially purchased by MGU HoldCo on the consummation of the Separation Transactions (the “MGU HoldCo Initial Shares”). See “Material Contracts and Related Party Transactions—Other—Common Shareholders Agreement” and “Description of Share Capital—Certain Provisions of the Amended and Restated Bye-Laws—Number of Directors” for a detailed description of these rights and the definition of “Shareholder Affiliate Transferees.”

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Our Business; Overview

We focus our business on three pillars: Bespoke, Specialty and Reinsurance (“Bespoke,” “Specialty” and “Reinsurance,” respectively). We believe our three-pillar strategy and capabilities allow us to take advantage of the opportunities presented by evolving (re)insurance markets and proactively shift our business mix across market cycles.

Bespoke

For the year ended December 31, 2022, the portion of the Group’s business which focuses on bespoke (re)insurance underwriting for tailored coverage (the “Bespoke pillar”) accounted for 26.1% of our GPW and 30.2% of our NPW with an underwriting ratio of 68.5% and a loss ratio of 31.3%. In 2022, the Bespoke pillar generated $119.3 million in underwriting income. GPW in the Bespoke pillar grew from $209.9 million for the year ended December 31, 2017 to $783.2 million for the year ended December 31, 2022, a compound annual growth rate of 30.1%, despite our decision to maintain our GPW in 2020 at the same level as in 2019 in light of political and economic uncertainties arising from the COVID-19 pandemic. During the period from 2017 to 2022, our average underwriting ratio was 57.7%. For the three months ended March 31, 2023 our Bespoke GPW grew to $150.8 million compared to $135.0 million for the three months ended March 31, 2022.

The Bespoke pillar focuses primarily on highly tailored and specialized products, including policies covering credit and political risk, political violence and terrorism, limited cyber reinsurance, tax liabilities, title, transactional liabilities and other bespoke products that fit our criteria. Given the increased global conflict in 2022 and national economies shifting further to intellectual property driven value, we believe that the Bespoke pillar continues to see significant opportunity for beneficial pricing and terms and conditions. The relationships we have formed with clients and brokers, the underwriting expertise required, and nature of the underlying risks create a higher barrier to entry and help us maintain our position as a leader in the industry. Typically, these lines do not follow the established (re)insurance cycle and are largely influenced by prevailing economic conditions at a given time. As such, these products require highly specialized pricing and other models tailored to the risk profile. For example, for certain significant risk transfer transactions, pricing is largely driven by counterparty credit quality which has low correlation with the current (re)insurance cycle and high correlation with the overall economy and macro events. As a result, Bespoke policies follow a different and diversified loss pattern relative to our Specialty and Reinsurance pillars.

The Bespoke portfolio has several economic features that we believe are financially attractive. The contracts often have multi-year tenors, and the products generally have expected low and stable attritional loss ratios over the exposure period. The combination of longer tenor and lower expected loss experience creates the potential to capture additional embedded value as premiums are earned over the exposure period under U.S. GAAP. Additionally, the contracts are highly capital-efficient as these risks tend to have little or no correlation to peak natural catastrophe perils driving a higher RoE than other lines. Furthermore, the contracts typically have customized provisions rather than standard market contractual provisions, creating opportunities to optimize pricing and establish proprietary, recurring relationships with clients. The custom and direct nature of the business has allowed us to lead on substantially all of our contracts creating tailored terms, conditions and pricing.

The Bespoke pillar benefits from quota share, aggregate and stop loss and excess of loss retrocessional cover, which helps to reduce volatility.

Our Bespoke pillar is central to our business, and we believe it is one of the key differentiators of our business from that of other specialty insurers. The specialist nature of this business combined with lower levels of market competition result in a less commoditized, more tailor-made product that delivers better and lower

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volatility underwriting performance with less exposure to the typical (re)insurance cycle. The capital-efficient nature of these products and potential for high RoE allow us to retain sufficient capital to withstand deterioration through (re)insurance cycles while avoiding accumulation of excess capital like many of our competitors focused primarily on high-volatility property reinsurance.

Specialty

For the year ended December 31, 2022, the portion of the Group’s business which focuses on traditional specialty business lines (the “Specialty pillar”) such as aviation, energy, space, marine, contingency and property direct and facultative (“D&F”) accounted for 53.7% of our GPW and 57.0% of our NPW with an underwriting ratio of 85.4% and a loss ratio of 59.7%. In 2022, the Specialty pillar generated $124.6 million in underwriting income. GPW in the Specialty pillar grew from $70.8 million for the year ended December 31, 2017 to $1,610.7 million for the year ended December 31, 2022, a compound annual growth rate of 86.8%. During the period from 2017 to 2022, our average underwriting ratio was 65.5%. For the three months ended March 31, 2023 our Specialty GPW grew to $834.1 million compared to $543.8 million for the three months ended March 31, 2022. Our Specialty pillar from 2017 to 2022 accounted for 13.0%, 6.4%, 12.2%, 36.7%, 41.0%, and 53.7%, respectively, of our GPW.

The Specialty pillar classes include aviation, energy, space, marine, contingency and property D&F. Given the current position of the reinsurance market in the insurance cycle, we have used our Specialty pillar increasingly to deploy capital targeted to natural catastrophe exposure through property D&F lines of business rather than through our Reinsurance pillar. We further capitalized on market dislocations and associated rate increases in key classes such as marine and aviation to increase the amount of business written. Our aviation, property D&F and marine businesses are among the leading franchise positions in the London market. The Specialty pillar benefits from quota share, aggregate, stop loss and excess of loss retrocessional cover and industry loss warranties, which helps to reduce volatility.

Our Specialty pillar provides us with access to capital-efficient business and facilitates diversification of our exposures. Due to the soft rate environment in years prior to 2020, this pillar has historically been the smallest contributor to our GPW. However, following the significant dislocation in the market beginning in late 2019 when a number of large carriers exited the Specialty market, Fidelis assessed that return hurdles in its Specialty pillar were at levels that had the potential to grow in this segment, and Fidelis increased its Specialty pillar GPW significantly in 2020 and 2021 (representing a 236% per annum GPW growth from 2019 to 2021) and continued to do so in 2022.

In 2022 and in the first quarter of 2023, we experienced further pricing momentum and enhanced terms and conditions as dislocations affected several lines, including war cover for marine and aviation lines driven by the Ukraine Conflict, contingency driven by COVID-19, and property D&F driven by Hurricane Ian.

In the Specialty pillar, we leverage Fidelis MGU’s ability to adapt to constantly evolving market dynamics and develop specialized and tailored pricing and aggregation models while maintaining a disciplined underwriting approach. Our underwriters work to form, and via the sophisticated underwriting expertise at Fidelis MGU we continue to develop, collaborative relationships with brokers and clients, offering them the full suite of our existing products as well as working with them to innovate new product ideas. This relationship-driven approach allows our underwriters, and will allow underwriters at Fidelis MGU on our behalf, to identify from existing clients additional underwriting opportunities for providing cover on other related lines of business. We typically seek out capacity-driven layers with attractive pricing, often focusing on dislocated markets, and look to ensure successful and sustainable growth in this pillar through developing and maintaining an excellent broker network.

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Reinsurance

For the year ended December 31, 2022, the Reinsurance pillar accounted for 20.2% of our GPW and 12.9% of our NPW with an underwriting ratio of 106.2% and a loss ratio of 74.3%. GPW in the Reinsurance pillar grew from $265.2 million for the year ended December 31, 2017 to $606.2 million for the year ended December 31, 2022, a compound annual growth rate of 18.0%. During the period from 2017 to 2022, our average underwriting ratio was 89.2%. For the three months ended March 31, 2023 our Reinsurance GPW was $260.4 million compared to $291.9 million for the three months ended March 31, 2022. Our Reinsurance pillar from 2017 to 2022 accounted for 48.6%, 47.4%, 45.9%, 41.8%, 38.9% and 20.2%, respectively, of our GPW.

Our Reinsurance pillar consists of an actively managed, primarily residential property catastrophe reinsurance book, with closely controlled aggregates using Fidelis MGU’s proprietary FireAnt aggregation and analytics system to monitor exposures in real time. The Reinsurance pillar also includes property retrocession and a limited amount of composite and multi-class asset reinsurance. In the context of excess of loss reinsurance products, we focus on underwriting attachment points largely exposed only to true catastrophe events. The portfolio is global in nature with a strong North American concentration and smaller exposures in Japan, Europe, Australasia and elsewhere throughout the world. The Reinsurance pillar benefits from quota share, aggregate, stop loss and excess of loss retrocessional cover, catastrophe bond cover and industry loss warranties, which helps to minimize the potential net losses in the business written. We believe our strategy of pursuing closely controlled aggregates and focusing on residential portfolios in the Reinsurance pillar helps keep volatility lower than a typical catastrophe book.

We benefit from Fidelis MGU’s sophisticated analytics capabilities and live aggregation tools, excellent relationships with a blend of regional and nationwide carriers (both in the United States and internationally), and strong retail and wholesale broker relations in the distribution of our products. Since 2021, we have developed a view of risk informed by thorough analysis and discussions with weather and forecasting experts. We have concluded that the effects of climate change on perils such as hurricanes, convective storm, flood and wildfire are not currently represented adequately in current vendor models. As such, we have superimposed our own expectations of frequency and severity on third-party vendor models, which are well in excess of average Bermuda (re)insurers’ loads, to form a base for exposure and aggregation tracking.

We have taken proactive steps to reduce volatility and reshape our Reinsurance portfolio to focus only on clients with stronger financial and loss adjustment capabilities and the resources to adjust and manage high volumes of claims in-house. As a consequence, the property reinsurance portfolio was reduced for the year ended December 31, 2022 and three months ended March 31, 2023, and subject to opportunities that may develop, is expected to remain at reduced levels for the remainder of 2023, reducing natural catastrophe exposure across the portfolio. We are increasingly deploying reinsurance capital across large-scale, well-resourced national accounts away from smaller regional underwriters, who we believe are less able to adjust and manage large catastrophe events. We have reduced our exposure to the middle layers of treaty accounts which are more exposed to increased frequency and severity of losses as a result of climate change and secondary perils associated with floods and wildfires without commensurate increases in rates. Following Hurricane Ian, we also saw an increased demand for private deals and significant pricing increases during the year-end renewal season. Over time, we expect the impact of these changes to improve the quality of our natural catastrophe-exposed portfolios and reduce volatility. As ever, we will continue to leverage our nimble underwriting abilities and ability to adapt to constantly evolving market dynamics to source business when favorable market conditions are present. If there is an increase in property catastrophe rates, as well as favorable terms and conditions, we would intend to capitalize on those trends and dislocations.

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Insurance Market Conditions

We believe we have significant market opportunities given our ability to innovate and adapt to evolving market conditions. Global economic and industrial development, population increases, greater product awareness and distribution, as well as inflation continue to drive increased need for insurance and reinsurance. The current insurance and reinsurance market environment has experienced a prolonged period of rate increases, structural enhancements and continued improvement of terms and conditions. However, we believe that the higher loss ratios experienced by many of our competitors in recent years due to the frequency and severity of catastrophes has caused some of them to reevaluate and reduce their catastrophe reinsurance business. As companies exit certain (re)insurance markets and/or reduce the scope of their underwriting activities, capacity has been reducing in certain classes, leading to significant year-on-year rate increases in the (re)insurance market since the end of 2019. Some classes of business that have experienced larger rate increases include property catastrophe, property D&F, specialty markets such as aviation, marine, energy and contingency and casualty markets such as medical malpractice and healthcare (with medical malpractice and healthcare being lines of business which Current Fidelis does not write) which is reflective of the hardening cycle being driven by a lack of underwriting profits rather than capital. We believe that this combination of factors is driving a sustainable favorable market environment, with a focus on risk management, disciplined risk selection, reasonable terms and profitable business, which presents significant market opportunities for us. Global commercial insurance prices rose 4% in the first quarter of 2023, making the first quarter of 2023 the tenth consecutive quarter of price increase since global pricing increases peaked at 22% in the fourth quarter of 2020¹. Property D&F pricing is at its highest level in two decades, marine cargo prices are at market highs and aviation pricing continues to remain strong. These rate increases are expected to persist throughout 2023 across the lines of business that FIHL focuses on. Rate increases across property D&F, marine, aviation and energy are expected to range between 10% to 40%, 7.5% to 10%, 50% to 100% and 30% to 50%, respectively, in 2023. In particular, we see the emergence of five themes supporting continued rate hardening:

• Climate Change. The frequency and severity of catastrophes is rising as seen by the increases in catastrophes globally in more recent years, requiring rate increases to keep pace. The period between 2017 and 2022, for example, saw three times the number of severe catastrophic weather events and twice the amount of losses caused by these severe events as compared to the period between 2011 and 2016. We believe that the impact of a warming climate and increased atmospheric moisture and changing weather patterns will result in increased frequency and severity of elemental catastrophe losses (elemental risks related to the elements i.e., weather related hail and storms etc.). The frequent incidence of annual industry-wide natural catastrophe losses in excess of $100 billion in the aggregate during the period from 2018 to 2022 has led us to reshape our portfolio and reduce our exposure to certain perils, thereby reducing the volatility traditionally associated with the property reinsurance classes. Many of our competitors have experienced higher loss ratios in the same period than in prior cycles and combined ratios in excess of 100%, causing them to reevaluate their levels of premiums written against catastrophe reinsurance (see “Business—Competition”). Decreased participation has created a lack of supply of reinsurance capacity causing upward pressure on price. We expect this trend to continue, which would allow Fidelis MGU to underwrite select attractive policies on our behalf and position us to deliver strong risk-adjusted returns.

• Casualty. We believe reserves across the industry remain deficient for accident years from 2013 to 2019 based on prior year adverse developments for several casualty underwriters. Further adverse developments and actual loss payouts may deplete competitors’ capital and impair their ability to underwrite additional casualty risks. Given Fidelis has made the strategic decision not to write the traditional casualty classes such as general liability, financial lines, directors and officers, and errors and omissions, it is not affected by these potential capital constraining issues, which we believe provides us with a competitive advantage due to our continued position of strength.

• Cost Inflation. Numerous countries including the United States are experiencing inflation in wages, materials and parts. Real inflation for expert loss adjusters and building materials, exacerbated following a

¹  Marsh Global Insurance Market Index Q1 2023.

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catastrophe, is causing an increase in loss ratios above modeled results for many insurers and complicating future estimates. This effect is increasing losses for multiple areas of the Excess & Surplus, Property & Casualty and reinsurance markets leading to rate increases and decreased appetite. Fidelis incorporates a specific cost inflation factor in its risk modeling to mitigate the effects of inflation. In addition, social inflation driven by changes in societal views on litigation aimed at insurers is a recent and developing risk highlighted by industry leaders and leading to larger claims. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Current Outlook, Market Conditions and Rate Trends.”

• Conflict. The escalation of geopolitical tensions and the ongoing invasion of Ukraine by Russia (the “Ukraine Conflict”) has created uncertainty and potential losses for both global direct insurers and reinsurers. Some lines of business are subject to asymmetrical loss profiles exacerbated by war and armed conflict, which are likely to reduce supply and/or accelerate rate changes. Additionally, aviation, marine, political risk and political violence lines are likely to be particularly impacted as insurers calibrate their losses, reserve, and court proceedings begin on potential claims. Fidelis continues to monitor the Ukraine Conflict to determine the ultimate impact from lines of business which may be exposed to the Ukraine Conflict, including aviation, marine, political risk and political violence contracts.

• COVID-19. Despite improving case and severity data, we believe industry losses since the beginning of the COVID-19 pandemic have not yet been fully captured. A significant number of outstanding claims and litigation beyond traditional mortality policies persists which may lead to changes in future policies and the risk-appetite of current underwriters. Recent judicial decisions in local markets have made adverse rulings relating to business interruption and treating each case as a separate claim with single claim limits. These rulings could affect the general interpretation of business interruption policies and may increase the level of insurers’ liability in the relevant markets by reducing their ability to aggregate policyholders’ losses when applying single claims limits. Fidelis has limited or no exposure to highly impacted businesses (such as U.K. commercial insurance, contingency (which Previous Fidelis began to write after the COVID-19 pandemic began in March 2020) and trade credit), and we continue to believe the effects of the COVID-19 pandemic will impact loss estimates for our competitors, future policies and competitor behavior.

These market conditions have led to a compelling dislocated underwriting opportunity in numerous specialty areas in which we underwrite.

Our Competitive Strengths

We believe that our competitive advantages are based on the following key strengths:

• Highly experienced, well regarded management team. Our management team consists of industry veterans with many years of relevant experience in insurance, providing FIHL with the necessary functional support, supplemented by the services stipulated under the Framework Agreement and Inter-Group Services Agreement. We are led by Mr. Daniel Burrows, who, prior to joining Fidelis in 2015, was the co-CEO of Aon Benfield’s Global ReSpecialty (“GRS”) division. Prior to assuming the CEO role at FIHL, Mr. Burrows had been leading Fidelis’ Bermuda operations and was most recently the Executive Chairman of FIBL and Group Managing Director. The other members of the management team are a mix of experienced individuals who have had held key roles at Fidelis and have long histories of working with Fidelis MGU, along with other experienced professionals from other industry peers.

• “First choice” access to one of the best underwriting teams in the industry. The performance of our business portfolio will be a direct result of the capabilities of the Fidelis MGU management team, led by Richard Brindle, who is the Chairman and CEO of Fidelis MGU. Mr. Brindle brings more than 38 years of experience in the insurance industry and is known for his track record of outperformance across Lloyd’s syndicates and Lancashire under his leadership. Mr. Brindle was acknowledged by A.M. Best in August 2018 to be one of the most successful underwriters in the worldwide insurance market and has a track record

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of outperformance over the past 30 years. From 2017 to 2022, the Fidelis MGU management team has outperformed peers across key profitability and growth metrics. Between 2017 and 2022, Fidelis achieved strong underwriting performance with an average loss ratio of 45.3% and an average combined ratio of 85.8%. In the three months ended March 31, 2023 our loss ratio was 41.3% and combined ratio was 79.1%, respectively. The Fidelis MGU management team brings many years of cumulative experience in broking, underwriting, corporate and actuarial roles as well as long-term client and broker relationships. Mr. Brindle previously founded Lancashire with over $1 billion of start-up capital in December 2005 and grew it into a key player in the (re)insurance market listed on the London Stock Exchange. Under the Framework Agreement, we secure business for a rolling term of 10 years, providing long-term certainty that we will leverage Fidelis MGU’s well-established and sophisticated underwriting capabilities. See “Material Contracts and Related Party Transactions” and “The Separation Transactions.”

• Significant scale achieved since establishment and clean platform for growth. We believe our scale achieved since inception and our access to Fidelis MGU’s sophisticated underwriting analytics and technology platform will give us a competitive advantage. Since we started underwriting in 2015, we have grown our insurance book significantly through organic business expansion including through increased client penetration, new product development, long-term relationships and new reinsurance partnerships. Between 2017 and 2022, we had extremely strong growth with a compound annual growth rate of 40.6% for GPW and compound annual growth rate of 47.0% for NPE compared to 13.7% and 11.5% respectively from other specialty insurers during the same period (including Arch, W. R. Berkley, Argo, Markel, Aspen, Everest Re, RenaissanceRe, Axis, Beazley, Hiscox, and Lancashire), while delivering top quartile underwriting profitability. Our GPW continued to grow in the three months ended March 31, 2023 to $1.2 billion compared with $1.0 billion in the three months ended March 31, 2022. As our long-tenor business lines (such as Bespoke products) continue to scale, we believe there will be higher convergence of NPE and NPW as prior period UPR continues to earn and have a favorable impact on NPE increasing.

• Strong capital position. We have a strong balance sheet and are committed to preserving our financial strength. At March 31, 2023, our total assets were $9.4 billion and our total cash and investments (including restricted cash) totaled $3.6 billion, primarily highly rated, liquid fixed maturity assets. Our $2.4 billion total capitalization (which includes our preference securities and issued debt) provides us with the flexibility to engage in attractive underwriting opportunities and scale quickly when market conditions warrant increased business.

• Nimble approach and focus on bottom line. We take pride in making reasoned decisions to actively enter and grow or reduce and exit specific lines of business as opportunity arises or diminishes, leveraging the UMCC to assess opportunities in real time with all key decision-makers. We believe our nimble approach and firm focus on bottom-line profitability (i.e., net income, as opposed to top-line growth) of each line of business is key to our strategy and success. We will establish our underwriting parameters and risk tolerances in respect of the three-pillar underwriting strategy in the Group Annual Plan, which will be prepared by Fidelis MGU in consultation with Current Fidelis and presented to Current Fidelis for formal approval on a gross/net basis.

Our strategy is to increase line sizes where appropriate, take the lead in requiring rate changes and establish ourselves as the “go to” market for solutions through our in-force portfolio and new classes of specialty and bespoke products. Depending on market conditions, Fidelis MGU, with our consent, may exercise its discretion in coordination with us to increase retention by reducing outwards quota shares to take further advantage of the continued hardening of rates. Similarly, we may also coordinate with Fidelis MGU to increase line sizes as conditions warrant. We intend to grow specialty classes by writing large line sizes to further push rate increases and access new classes where there is significant market dislocation. We expect to grow our bespoke and specialty products through a combination of organic growth of our already well-established footprint, systematic cross-selling to clients and innovative new products while maintaining quality underwriting information, high-quality risk selection and multi-line aggregation tools and technology.

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• Access to well-diversified, multi-line (re)insurance risk. We prioritize pursuing a targeted diversification strategy focused on three pillars – Bespoke, Specialty and Reinsurance. We have built a portfolio leveraging our ability to remain agile across market cycles with 74 lines of business across our three pillars at March 31, 2023. Our products serve numerous industries, types of exposure, and geographies. We believe that Fidelis MGU’s ability to price and aggregate bespoke risks, adapt to evolving market dynamics in the specialty market, and continually optimize in reinsurance markets uniquely positions us to continue to grow a profitable portfolio. The breadth of our portfolio offering in conjunction with our partnership with Fidelis MGU also allows us to adjust line sizes and retention rates based on prevailing market conditions and achieve optimal economics for the overall portfolio. The three-pillar strategy is central to our growth as it allows us to deliver attractive risk-adjusted returns to shareholders in the long term by managing through (re)insurance cycles and deploying to the most favorable market conditions across the three pillars.

• Innovative product offering positioned for continued growth. We focus on building first mover advantages across our markets. Our product portfolio evolves in response to client demand for bespoke, tailored products and our market-driven, real-time assessment of risk. Over the past four years, we have grown our book of newly created solutions across a wide range of sectors including airline, intellectual property, marine, and residential mortgage, expanding our business lines to 74 lines at March 31, 2023 from 43 at December 31, 2017. Through this innovation, we have further strengthened our three-pillar strategy and our position as a skilled specialty insurer.

• Proprietary technology integration with full control of data. We will continue to leverage Fidelis MGU’s proprietary and sophisticated technology platform. As a business that was established in 2014, Fidelis had the benefit of building a proprietary underwriting platform free from constrained legacy systems. We believe that the technology platform, which is owned by Fidelis MGU, has significant advantages over our competitors. It is our understanding, that many peers use hybrid platforms built more than a decade ago, that spread between various fragmented modules which reduce their agility and make it difficult to effectively analyze real-time data. Fidelis has a single holistic pricing, aggregation and analytics platform (i.e., FireAnt), which helps us avoid key pitfalls of other systems including: time wasted in duplicating data entry across multiple systems, inconsistency of modeling and pricing approach, inability to raise queries across multiple lines simultaneously, no direct link offered to outwards reinsurance and capital structures, and lag time for those other systems to respond to emerging risks. The technology platform will enable Fidelis MGU to take full control of data with no “black box” third-party assumptions. We believe that the platform leverages high-quality outside software with custom tools developed purposefully and in-house with the ability to aggregate and analyze data on a real-time basis. This includes third-party risk models and software, Jarvis (a custom integrated group data warehouse), Tyche (third-party capital modeling application), Prequel (a custom policy administrative system) and FireAnt (a custom pricing, simulation, exposure aggregation, and portfolio optimization tool). FireAnt allows for optimization of returns and management of volatility and capacity based on real time data. The highly specialized data capabilities developed and presently in use by Fidelis have driven enhancement in underwriting across Bespoke and Specialty lines including marine, aviation and terrorism where live data is actively analyzed to unlock new opportunities.

• Embedded ESG initiatives that are core to our business. We believe our commitment to ESG and following the initiatives set out below is core to our success as a business. In order to have a practical and value accretive approach to implementation of ESG considerations, we have adopted the following as key areas of focus: animal welfare, armaments, capital punishment, coal and arctic drilling, anti-slavery/human trafficking and diversity, equity and inclusion. Fidelis MGU will continue to incorporate an ESG assessment into its underwriting on our behalf and is continually refining its process for reviewing individual insurance risks. Fidelis in the U.K. market has promoted the use of a forced labor clause prohibiting the use of any form of forced labor in marine cargo business and is cooperating with the U.K. Independent Anti-Slavery commissioner and Anti-Slavery International, a non-profit organization to develop a commitment to which insurers and brokers can sign up. In 2022, we implemented forced labor clauses in approximately 80% of our marine cargo accounts.

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Fidelis MGU is the first U.K. market insurer to sign up to The Poseidon Principles on Marine Insurance which pledges a net zero marine hull insurance portfolio by 2050. We actively support the transition to a net zero global economy by making renewable energy one of our classes of underwriting, including the construction of offshore wind turbine farms. Fidelis and Fidelis MGU are both members of ClimateWise. The ClimateWise Principles require members to disclose their responses to the risks and opportunities of climate change and which principles are aligned with the Task Force on Climate-related Financial Disclosure framework. So long as we remain a member we intend to report annually on actions taken in support of those principles.

We drive employee engagement through opportunities for employees that we believe help them live out their values at work. The employee-led Fidelis Insurance Green Team, which has representatives from each office, suggests ways to reduce our corporate carbon impact and improve recycling rates, such as our carbon usage offset. We support social mobility and diversity in our communities through our support for The Brokerage, a social mobility charity (a number of whose interns have become our full-time employees) and the Afro-Caribbean Insurance Network.

We maintain underwriting and investment restrictions that align with our ESG principles as well as those principles that are consistent with leading to long-term value, such as excluding a number of sectors that we believe pose risks of harm to people, animals and the environment. Furthermore, FIHL’s investment portfolio is managed in a manner that is consistent with Fidelis’ sustainability principles and its ESG objectives. The core fixed maturity portfolio has target GSS investment thresholds, prohibits issuers with poor ESG ratings, and restricts certain industries and behaviors.

Our Strategy

We are set up to be nimble, thoughtful, and efficient decision-makers and we believe that we are able to respond quickly to an ever-changing world and a constantly evolving marketplace. We believe these attributes allow us, together with Fidelis MGU, to target opportunities that we expect to offer a compelling balance of risk and reward for our shareholders. We intend to continue to scale our business when favorable market conditions are present, pursue prudent capital management and profitable underwriting on a loss ratio and combined ratio basis, and target an Operating RoE of approximately 13.0% to 15.0%. Our strategy involves the following:

• Expand our presence in Bespoke and Specialty. We expect to continue to leverage our access to Fidelis MGU’s long-standing and trusted relationships with brokers and clients, built over the years by key executives, some of whom have almost 40 years of experience in bespoke and specialty markets. Fidelis MGU intends to continue to follow a structured approach with regard to maintaining such relationships through its participation in industry events and through continuing to hold regularly scheduled meetings with clients and brokers, thereby preserving access to CEOs and senior management teams of its most important business partners. The continued access to such long-standing and trusted relationships coupled with Fidelis MGU’s extensive expertise will provide significant opportunity to quote, underwrite and bind attractive niche specialty insurance policies in an efficient manner. By focusing on markets in which Fidelis MGU has particular expertise and in which we can provide new, innovative products, we believe we have a strong ability to capture profitable business. The Bespoke and Specialty pillars have benefited from a hardening pricing environment over recent years which has enhanced our recent profitability ratios. In keeping with our nimble approach and leveraging the UMCC, where all lines of business are considered in real time, we expect Fidelis MGU (and consequentially, Current Fidelis) to be able to pivot quickly to the most attractive opportunities. Currently, we expect a hard property reinsurance market will further continue in 2023 and into 2024 and we are planning to take advantage of reinsurers’ increased bargaining power in such hard market to reduce our aggregate exposures. As a result, in our Bespoke pillar, in line with the current economic outlook, we expect to limit the growth in traditional mortgage products and focus instead on lines such as intellectual property, political violence, political risk and transactional liabilities. In our Specialty pillar, we expect the aviation market to continue the hardening of previous rates following potential losses from the Ukraine Conflict. Similarly, the

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property D&F market is also expected to harden further following losses from Hurricane Ian, which impacted Florida and the American southeast in September 2022. Based on 2022 GPW, Europe is currently our leading market, closely followed by North America, with a smaller portion of our business in Asia and other jurisdictions. The (re)insurance business we write across our Bespoke, Specialty and Reinsurance pillars can be analyzed by geographic region, reflecting the location of the (re)insurer as follows: for the year ended December 31, 2022 our GPW generated for exposures in Europe was 50.6%, in North America was 37.4% and in Asia was 5.9%, while GPW in other jurisdictions was 6.1%. Although we do not expect a significant change to the geographic mix of our business, we will continue to focus on developing new and innovative products in response to market needs, remaining agile and nimble to the developing demands of clients. A recent example of such innovation is the cooperation between Previous Fidelis and Aon in 2021 on developing a product that allows early stage companies to leverage their intellectual property with a credit wrap insurance product to reduce the costs and increase the availability debt finance from lending institutions. Furthermore, in 2022 Previous Fidelis led the development of an aviation product that, once deployed, will provide a real-time quoting service for airlines and airline service providers to reinstate cover if the provision immediately cancelling cover is triggered as a result of a detonation of a nuclear device in their compulsory insurance coverages.

• Generate underwriting profits. We will continue to focus on underwriting profitably through (re)insurance cycles in partnership with Fidelis MGU. As our insurance portfolio matures and scales, we believe we will also have an opportunity to increase our underwriting leverage. We seek to direct capital to opportunities based on market conditions to address client needs at better pricing opportunities. We will leverage our relationship with Fidelis MGU to continue disciplined underwriting via the use of Fidelis MGU’s integrated technology solutions, including monitoring real-time market conditions to best capture unique opportunities.

Fidelis MGU’s robust daily processes will enable it, on our behalf, to maintain a live, dynamic picture of the current underwriting environment that drives daily underwriting decisions, including our daily UMCCs. We believe that our risk selection as a result of these robust processes should allow us to deploy significant line sizes that in turn allow us to be a “rate maker” rather than a “rate taker.”

• Maintain diversification and low volatility. We seek to maintain significant diversification in our business lines which limits the correlations to single events. Our strategy has frequently generated better risk-adjusted returns than many of our competitors who focus on specific niches exclusively or have large exposure to natural catastrophe reinsurance. We have taken measures with Fidelis MGU to actively manage and in many cases reshape our natural catastrophe exposure in light of greater severity and frequency of catastrophe events and concerns around global climate change.

• Uphold a strong balance sheet. We believe as interest rates rise, we will have opportunities to earn a higher yield while maintaining an appropriately conservative investment portfolio to support our business. We maintain robust procedures for setting our reserves and actively managing risk in our portfolio. From January 1, 2017 to March 31, 2023, we had net favorable prior year reserve development of $155.6 million from our reserves. We believe a robust balance sheet best positions us to be a provider of choice for policyholders and take advantage of large or sudden market pricing dislocations.

• Manage capital prudently. We invest and manage our capital proactively with a goal of generating strong RoE for investors. We believe market conditions will continue to warrant expansion of our premium volume and capital base to take advantage of attractive opportunities. Our goal is for our capital returns program to be focused on ordinary payouts from operating net income and releasing excess capital as appropriate, while balancing any return of capital with the need to take a prudent and efficient approach to capital sufficiency. We believe successful underwriting will allow us to grow our equity and support continued premium growth with an increased ability to fund growth from our own resources and return excess capital to shareholders over time, which may take the form of ordinary dividends, special dividends or share buybacks. Over the full market cycle, we expect to have additional opportunities to manage our capital in order to maintain an appropriate RoE for our shareholders which may include returning excess capital when market opportunities are limited in soft insurance markets.

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Summary Risk Factors

Investing in the Common Shares involves risks. Prospective investors should carefully consider the risks described in “Risk Factors,” below, as well as other information contained in this prospectus before making an investment decision. Any of the factors set forth under “Risk Factors” could materially adversely affect our business, financial condition, results of operations or cash flows and could impact any forward-looking statements. Prospective investors should note that such risks are not the only ones we face. Additional risks and uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect us in the future. Among these important risks are the following:

• the inherent uncertainties of modeling and reserving processes on which we rely and failure of any risk management and loss limitation methods we employ;

• the impact of the current global geopolitical environment, including the ongoing COVID-19 pandemic and the Ukraine Conflict, and changing climate conditions;

• the level of success of our acquisition and investment strategies;

• the high level of competition and consolidation in our industry;

• a downgrade or withdrawal of, or other negative action relating to, the financial strength rating(s) by insurance rating agencies;

• loss of business reputation or negative publicity, including as a result of litigation or coverage disputes;

• our ability to retain and recruit key personnel;

• industry and market conditions, volatility and developments, which could impact our investment portfolio;

• our ability to adjust to developments in the legal, economic, tax or regulatory environment;

• the volatile, unpredictable and highly cyclical nature of the industry in which we operate;

• our exposure to low frequency, high severity events;

• the impact of any deterioration or termination of our relationship with Fidelis MGU;

• our reliance on third parties for certain critical business operations; and

• the other factors identified under the heading “Risk Factors” beginning on page 33 of this prospectus.

The Separation Transactions

On July 23, 2022, a cooperation agreement was entered into among FIHL, MGU HoldCo and certain third-party investors in Shelf Holdco Ltd., the MGU HoldCo parent company and the ultimate holding company of Fidelis MGU (“MGU TopCo”) (the “Cooperation Agreement”) agreeing to cooperate regarding certain matters related to this offering and the furtherance of the Separation Transactions. See “Material Contracts and Related Party Transactions—Cooperation Agreement.” On January 3, 2023, the Separation Transactions were completed and two distinct holding companies and businesses were created: FIHL and MGU HoldCo.

FIHL is the parent holding company for Current Fidelis. It is the issuer of the Common Shares sold by the Selling Shareholders in this offering and owns all of the operating insurance carrier subsidiaries of Current Fidelis, comprising FIBL, FUL and FIID.

MGU HoldCo is the parent holding company for Fidelis MGU that carries on the origination and underwriting activities on behalf of Current Fidelis. MGU HoldCo’s principal operating subsidiaries are Bermuda MGU, Pine Walk Capital and Pine Walk Europe. The underwriting activities of each of the licensed insurance carriers of Current Fidelis (FIBL, FUL and FIID) are outsourced to the corresponding operating subsidiaries of Fidelis MGU on a jurisdictional basis (Bermuda MGU, Pine Walk Capital and Pine Walk Europe,

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respectively). Each of the operating subsidiaries of Fidelis MGU has delegated underwriting authority to source and bind contracts for and on behalf of each of FIBL, FUL and FIID, respectively. See “Material Contracts and Related Party Transactions—Framework Agreement.” MGU HoldCo and its subsidiaries will not be consolidated with FIHL and its subsidiaries.

Current Fidelis also has a U.K. service company, FIHL (UK) Services, with a branch in Ireland. MGU HoldCo owns 100% of the outstanding shares of FML, a U.K. service company (which also has a branch in Ireland).

Our Corporate Structure

The following chart presents a simplified summary overview of the corporate structure for Current Fidelis, which, other than the percentage ownership changes noted at note (1) below, will remain unchanged following the consummation of this offering. For a more detailed description of our organizational structure and an overview of the Separation Transactions see “The Separation Transactions.”

Current Fidelis Structure

(1) See “Principal and Selling Shareholders” for detail of the percentage ownership prior to this offering, as well as the percentage ownership of FIHL following the consummation of this offering (including in the event of a full option exercise) by each of MGU HoldCo, the Founders, other institutional investors, management and other existing shareholders.

(2) FUL is a limited liability company incorporated in England and Wales, authorized by the Prudential Regulation Authority (“PRA”), and supervised by the Financial Conduct Authority (“FCA”) and the PRA as an insurer.

(3) FIBL is a limited liability company incorporated in Bermuda, authorized and supervised by the BMA as an insurer.

(4) FIHL (UK) Services is a limited liability company incorporated in England and Wales and is the service company of Current Fidelis. FIHL (UK) Services also has a branch in Ireland.

(5) Fidelis European Holdings Limited (“FEHL”) is a limited liability company incorporated in England and Wales.

(6) FIID is a designated activity company incorporated in Ireland, authorized and supervised by the Central Bank of Ireland (“CBI”) as an insurer.

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Director Nomination Rights

Under the terms of the Amended and Restated Common Shareholders Agreement, MGU HoldCo and certain of the existing major investors in FIHL will be entitled to nominate representative directors to the Board, so long as they each beneficially own a specified minimum percentage of our Common Shares. Under the terms of the Amended and Restated Common Shareholders Agreement, the right to nominate one individual (a “Nominee”) to serve as a director on the Board will be afforded to each of the Crestview Funds (as defined below, see “Principal and Selling Shareholders”), CVC Falcon Holdings Limited (“CVC”) and Pine Brook Feal Intermediate L.P. (“Pine Brook”) (each a “Founder” and together, the “Founders”) and to MGU HoldCo, so long as they each beneficially own a specified minimum percentage of our Common Shares. Under the terms of the Amended and Restated Common Shareholders Agreement, if a Nominee is not appointed or elected to the Board because of such person’s death, disability, disqualification, withdrawal as a Nominee, failure to be elected or for another reason is unavailable or unable to serve on the Board, the applicable nominating Founder or MGU HoldCo shall be entitled to designate promptly another Nominee, the director position for which the original Nominee was nominated shall not be filled pending such designation and FIHL shall use commercially reasonable efforts and consistent with NYSE corporate governance standards to cause the Board to promptly fill the vacancy with such successor Nominee.

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The Offering

Issuer: Fidelis Insurance Holdings Limited

Common Shares offered by us 5,714,286 Common Shares.

Common Shares offered by the Selling Shareholders 11,285,714 Common Shares.

Common Shares outstanding after this offering 116,486,183 Common Shares.

Underwriters’ option to purchase additional Common Shares from the Selling Shareholders The Selling Shareholders have granted the underwriters an option to purchase up to an additional 2,550,000 Common Shares at the public offering price less underwriting discounts and commissions, for 30 days after the date of this prospectus.

Use of proceeds We estimate that the net proceeds to us from the sale of Common Shares from this offering will be approximately $87.7 million based upon the assumed initial public offering price of $17.50 per Common Share, which is the midpoint of the estimated offering price range set forth on the cover page of this prospectus, and after deducting the estimated underwriting discounts and estimated offering expenses payable by us. An increase in the offering price above the midpoint of the estimated offering price range set forth on the cover page of this prospectus will result in us selling fewer Common Shares such that our gross proceeds will not exceed $100.0 million. We will not receive any of the proceeds from the sale of our Common Shares in this offering by the Selling Shareholders.

We intend to use the net proceeds to us from this offering to make capital contributions to our insurance operating subsidiaries, which, together with other sources of liquidity, should enable us to take advantage of the ongoing rate hardening in the key markets in which we participate by writing more business under our planned strategy (as discussed in more detail in “Business—Our Strategy” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Liquidity and Capital Resources”). See “Use of Proceeds” for a more complete description of the intended use of proceeds from this offering.

Dividend Policy Any decision to declare and pay dividends in the future will be made at the sole discretion of our Board and will depend on various factors. See “Dividend Policy.”

Exchange Symbol FIHL.

Risk Factors See “Risk Factors” beginning on page 33 and other information included in this prospectus for a discussion of factors you should carefully consider before deciding to invest in our Common Shares.

Listing We have applied to list our Common Shares on NYSE under the symbol “FIHL.”

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Except as otherwise indicated, the number of Common Shares outstanding after this offering:

• excludes 3,654,605 Common Shares (plus an additional number of Common Shares equal to 4.0%, on a fully diluted basis, of the Common Shares sold by us from this offering) reserved for issuance under our long-term 2023 share incentive plan (the “Long-Term Incentive Plan”);

• excludes 960,895 Common Shares underlying restricted share unit awards granted under the Long-Term Incentive Plan as of June 9, 2023;

• gives effect to a 1-for-.92 reverse stock split of our Common Shares effected on June 16, 2023;

• assumes an initial public offering price of $17.50 per Common Share, which is the midpoint of the price range set forth on the cover page of this prospectus; and

• assumes the underwriters’ option to purchase additional Common Shares from the Selling Shareholders will not be exercised.

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SUMMARY FINANCIAL AND OPERATING DATA

The tables below present summary financial and operating data at, and for, the periods indicated. The following information is only a summary and should be read in conjunction with the section entitled “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and the audited consolidated financial statements and the accompanying notes included elsewhere in this prospectus.

The summary balance sheet data at March 31, 2023, December 31, 2022 and 2021 and the summary statement of operations data for the three months ended March 31, 2023 and 2022, and for the years ended December 31, 2022, 2021 and 2020 have been derived from our unaudited consolidated financial statements for the three months ended March 31, 2023 and 2022 and audited consolidated financial statements for the years ended December 31, 2022, 2021 and 2020, included elsewhere in this prospectus. We have included, in our opinion, all adjustments necessary to state fairly our results of operations for those periods.

These historical results are not necessarily indicative of the results that may be expected for any future period.

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SUMMARY STATEMENT OF OPERATIONS DATA

	Three months ended March 31,						Year ended December 31,
	2023			2022			2022			2021			2020
	($ in millions)
Revenues
Gross premiums written	$	1,245.3		$	970.7		$	3,000.1		$	2,787.7		$	1,576.5
Reinsurance premiums ceded		(585.6	)		(485.4	)		(1,137.5	)		(1,186.6	)		(670.9	)
Net premiums written		659.7			485.3			1,862.6			1,601.1			905.6
Change in net unearned premiums		(273.7	)		(163.5	)		(357.9	)		(446.9	)		(177.0	)
Net premiums earned		386.0			321.8			1,504.7			1,154.2			728.6
Net investment gains/(losses)		2.8			(10.2	)		(33.7	)		13.5			17.9
Net investment income		20.4			5.1			40.7			20.6			26.2
Net foreign exchange gains		—			—			6.8			—			1.2
Other income		3.5			1.0			1.9			1.0			8.7
Total revenues before net gain on distribution of Fidelis MGU		412.7			317.7			1,520.4			1,189.3			782.6
Net gain on distribution of Fidelis MGU		1,639.1			—			—			—			—
Total revenues		2,051.8			317.7			1,520.4			1,189.3			782.6
Expenses
Losses and loss adjustment expenses		159.6			178.4			830.2			696.8			324.5
Policy acquisition expenses(1)		129.2			67.7			447.7			299.9			179.2
General and administrative expenses		16.6			35.5			106.4			75.4			83.5
Corporate and other expenses		1.5			1.9			20.5			2.7			18.7
Net foreign exchange losses		1.5			0.9			—			0.4			—
Financing costs		8.6			8.8			35.5			35.4			27.9
Loss on extinguishment of preference securities		—			—			—			—			25.3
Total expenses		317.0			293.2			1,440.3			1,110.6			659.1
Income before income taxes		1,734.8			24.5			80.1			78.7			123.5
Income tax (expense)/benefit		(2.2	)		(4.7	)		(17.8	)		(0.4	)		3.1
Net income		1,732.6			19.8			62.3			78.3			126.6
Net income attributable to non-controlling interests		—			(2.8	)		(9.7	)		(10.0	)		(0.1	)
Net income available to common shareholders		1,732.6			17.0			52.6			68.3			126.5

(1) See note 2 of the unaudited consolidated financial statements for the three months ended March 31, 2023 and 2022. Commissions on ceded business are presented within policy acquisition expenses in the three month periods ended March 31, 2023 and 2022. Commissions on ceded business are presented within general and administrative expenses in the years ended December 31, 2022, 2021 and 2020.

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SUMMARY BALANCE SHEET DATA

	At March 31, 2023		At December 31,
			2022		2021
	($ in millions)
Assets
Total investments	$	2,840.6	$	2,425.0	$	2,782.6
Cash and cash equivalents and restricted cash and cash equivalents		711.4		1,407.9		476.0
Reinsurance balances
Reinsurance balances recoverable on paid losses		96.5		159.4		256.6
Reinsurance balances recoverable on reserves for losses and loss expenses		1,032.8		976.1		795.2
Deferred reinsurance premiums		1,191.7		823.7		676.7
Other assets		1,121.7		657.7		510.7
Premiums and other receivables		2,387.5		1,862.7		1,555.2
Total assets	$	9,382.2	$	8,312.5	$	7,053.0
Liabilities, and shareholders’ equity
Liabilities
Reserves for losses and loss adjustment expenses	$	2,215.0	$	2,045.2	$	1,386.5
Unearned premiums		3,260.3		2,618.6		2,113.7
Reinsurance balances payable		1,221.5		1,057.0		947.8
Long term debt		447.7		447.5		446.9
Preference securities		58.4		58.4		58.4
Other liabilities		274.8		98.7		80.6
Total liabilities		7,477.7		6,325.4		5,033.9
Commitments and contingencies
Shareholders’ equity
Total shareholders’ equity including non-controlling interests		1,904.5		1,987.1		2,019.1
Total liabilities and shareholders’ equity	$	9,382.2	$	8,312.5	$	7,053.0

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OTHER DATA

	Three months ended March 31,						Year Ended December 31,
	2023			2022			2022			2021			2020
	($ in millions)
Loss ratio(1)		41.3	%		55.4	%		55.2	%		60.4	%		44.5	%
Policy acquisition expense ratio(2)		27.2	%		21.0	%		29.8	%		26.0	%		24.6	%
Underwriting ratio		68.5	%		76.4	%		85.0	%		86.4	%		69.1	%
Fidelis MGU commission ratio(3)		6.3	%		—	%		—	%		—	%		—	%
General and administrative expense ratio(4)		4.3	%		11.0	%		7.1	%		6.5	%		11.5	%
Combined ratio(5)		79.1	%		87.4	%		92.1	%		92.9	%		80.6	%
Net investment gains/(losses)	$	2.8		$	(10.2	)	$	(33.7	)	$	13.5		$	17.9
Net investment return(6)	$	23.2		$	(5.1	)	$	7.0		$	34.1		$	44.1
Debt to total capitalization ratio(7)		21.0	%		20.3	%		20.2	%		20.0	%		20.3	%
Fully diluted book value per share(8)	$	17.19		$	9.89		$	9.91		$	10.05		$	11.50
RoE(9)		87.6	%		0.8	%		2.6	%		3.5	%		11.3	%
Operating RoE(10)(11)		5.4	%		1.0	%		3.3	%		3.6	%		14.9	%

(1) Ratio, in percent, of losses and loss adjustment expenses to NPE.

(2) Ratio, in percent, of policy acquisition expenses paid to third parties to NPE. See note 2 of the unaudited consolidated financial statements for the three months ended March 31, 2023 and 2022 included elsewhere in this prospectus. Commissions on ceded business are presented within policy acquisition expenses in the three month periods ended March 31, 2023 and 2022. Commissions on ceded business are presented within general and administrative expenses in the years ended December 31, 2022, 2021 and 2020.

(3) Ratio, in percent, of Fidelis MGU commissions to NPE.

(4) Ratio, in percent, of general and administrative expenses to NPE. See note (2) above for explanation of the presentation of commissions on ceded business.

(5) Ratio, in percent, of the sum of losses and loss adjustment expenses, policy acquisition expenses paid to third parties, Fidelis MGU commissions and general and administrative expenses to NPE.

(6) Net investment return includes net investment income plus net investment gains and losses.

(7) Ratio, in percent, of total long-term debt and preference securities to total capitalization. The total capitalization comprises shareholders’ equity including non-controlling interests plus total long-term debt and preference securities.

(8) Represents the equity attributable to Fidelis Common Shareholders divided by the sum of the Common Shares outstanding and the dilutive impact of “in the money” outstanding warrants and RSUs.

(9) Ratio, in percent, of net income to opening common shareholders’ equity.

(10) Ratio, in percent, of operating net income to opening common shareholders’ equity.

(11) Operating RoE is a non-U.S. GAAP measure. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Performance Measures and Non-U.S. GAAP Financial Measures—Operating Net Income, RoE and Operating RoE” for a reconciliation to the most directly comparable financial measure stated in accordance with U.S. GAAP.

Summary Unaudited Pro Forma Condensed Combined Financial Information

The summary unaudited pro forma condensed combined financial information presented below consists of the summary unaudited pro forma condensed combined balance sheet at December 31, 2022, the summary unaudited pro forma condensed combined statement of income for the year ended December 31, 2022 and the notes thereto. The unaudited pro forma condensed combined financial information should be read in conjunction with the information included under “The Separation Transactions,” “Unaudited Pro Forma Condensed Combined Financial Information” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and our audited combined financial statements and the accompanying notes included elsewhere in this prospectus. The summary unaudited pro forma condensed combined financial information presented below is useful to investors because it provides a view of our results of operations for the period presented giving effect to the Separation Transactions (which were consummated on January 3, 2023) as if the Separation Transactions had occurred at the beginning of such period. The summary unaudited pro forma

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condensed combined balance sheet at December 31, 2022 has been prepared to give effect to the Separation Transactions as if these transactions had occurred on December 31, 2022.

The summary unaudited pro forma condensed combined statement of income for the year ended December 31, 2022 has been prepared to give effect to the Separation Transactions as if these transactions had occurred on January 1, 2022.

The unaudited pro forma condensed combined financial information is presented for informational purposes only and does not purport to represent our financial condition or our results of operations had these transactions occurred on or at the dates noted above or to project the results for any future date or period. The unaudited pro forma condensed combined financial information has been prepared in accordance with Regulation S-X. Actual results may differ from the pro forma adjustments.

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SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED INCOME STATEMENT

SELECTED STATEMENT OF OPERATIONS DATA

	December 31, 2022 Pro Forma Statement of Operations
	$ in millions
Revenues
Gross premiums written	$	2,989.8
Reinsurance premiums ceded		(1,142.9	)
Net premiums written		1,846.9
Change in net unearned premiums		(357.9	)
Net premiums earned		1,489.0
Net investment losses		(33.7	)
Net investment income		40.6
Net foreign exchange gains		4.1
Net gain on distribution of Fidelis MGU		1,638.1
Other income		0.3
Total revenues	$	3,138.4
Expenses
Losses and loss adjustment expenses		830.2
Policy acquisition expenses (includes Fidelis MGU commissions of $119.5)		529.4
General and administrative expenses		71.1
Corporate and other expenses		18.6
Financing costs		35.5
Total expenses	$	1,484.8
Net income before tax		1,653.6
Income tax expense		(1.3	)
Net income	$	1,652.3
Net income attributable to non-controlling interests		—
Net income available to common shareholders	$	1,652.3
Other comprehensive gain (loss)
Unrealized loss on AFS assets		(96.5	)
Income tax benefit		8.1
Currency translation adjustments		—
Total other comprehensive loss	$	(88.4	)
Comprehensive gain (loss) attributable to common shareholders	$	1,563.9

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SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED BALANCE SHEET

	December 31, 2022 Pro Forma Balance Sheet
	$ in millions
Assets
Fixed maturity securities, available-for-sale at fair value	$	2,050.9
Short-term investments, available-for-sale at fair value		257.0
Other investments, at fair value		117.1
Total investments		2,425.0
Cash and cash equivalents		990.5
Restricted cash and cash equivalents		185.9
Derivative assets, at fair value		6.3
Accrued investment income		10.9
Investments pending settlement		2.0
Premiums and other receivables		1,872.0
Deferred reinsurance premiums		823.7
Reinsurance balances recoverable on paid losses		159.4
Reinsurance balances recoverable on reserves for losses and loss adjustment expenses		976.1
Deferred policy acquisition costs		516.0
Deferred tax asset		51.2
Operating right of use assets		26.8
Other assets		25.6
Total Assets	$	8,071.4
Liabilities and Shareholders’ equity
Liabilities
Reserves for losses and loss adjustment expenses		2,045.2
Unearned premiums		2,618.6
Reinsurance balances payable		1,057.0
Long term debt		447.5
Preference securities		58.4
Other liabilities		17.8
Operating lease liabilities		28.5
Total Liabilities	$	6,273.0
Shareholders’ equity
Ordinary shares		1.9
Additional paid-in capital		1,942.8
Accumulated other comprehensive loss		(99.7	)
Accumulated deficit		(46.6	)
Total shareholders’ equity attributable to common shareholders	$	1,798.4
Non-controlling interests		—
Total shareholders’ equity including non-controlling interests	$	1,798.4
Total liabilities and shareholders’ equity	$	8,071.4

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RISK FACTORS

Investing in the Common Shares involves risks. Prospective investors should carefully consider the risks described below, as well as other information contained in this prospectus before making an investment decision. The risks described below are not the only ones we face. Additional risks and uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect us in the future. Any of the following risks could materially adversely affect our business, financial condition, results of operations or cash flows and could impact any forward-looking statements. See “Cautionary Note Regarding Forward-Looking Statements.” In such case, the trading price of the Common Shares may decline and investors may lose all or part of their original investments.

For the purposes of this section, references to the “Group” shall refer to (i) prior to the consummation of the Separation Transactions and this offering to Previous Fidelis and (ii) following the consummation of the Separation Transactions to Current Fidelis, as the context requires.

Risks Relating to the Group’s Business and Industry

Underwriting of insurance can be volatile and unpredictable. This dynamic, combined with the Group’s exposure to low-frequency, high-severity events, may result in substantial losses and insurance underwriting results can vary across the industry and across different years.

The underwriting of insurance risks is, by its nature, a high-risk business. Earnings can be volatile and losses may be incurred that have the effect of significantly reducing the net profit or capital position of the Group. Although the Group’s underwriting is generally focused on low-frequency, high-severity losses worldwide, the frequency and unpredictability of such losses has significantly increased in the last couple of years due to, among other things, changing climate conditions. The result of this underwriting strategy is that the Group’s results may be subject to unpredictable losses or the potential of more than one loss occurring at the same time.

It is inherent in the nature of the insurance business that it is difficult to forecast short-term trends or returns, including for the Group. The results of companies in the insurance industry worldwide vary widely as do the results of insurers operating within the Bermuda, London and European insurance markets. Even if the Bermuda, London and European insurance markets make an overall profit, some individual insurers or lines of business may incur losses. The past results of the markets and the Group’s historical results, as well as the results of the Group’s peers, are a historical record only and may not necessarily be a reliable guide to future prospects.

Underwriting risks and reserving for losses are based on probabilities, assumptions and related modeling, which are subject to inherent judgment and uncertainties and may materially impact the Group’s business, prospects, financial condition or results of operations.

Underwriting is a matter of judgment, involving important assumptions about matters that by their nature are unpredictable and beyond the control of the Group and for which historical experience and probability analysis may not provide sufficient guidance. One or more catastrophic or other events could result in claims that substantially exceed the Group’s modeled loss expectations, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. A single event could result in significant losses across multiple classes of the Group’s business. Certain risks are harder to model, and the Group estimates the impact of these through aggregate exposure and non-probabilistic modeling. The inherent uncertainties underlying, or incorrect usage or misunderstanding of, both aggregate exposure and non-probabilistic modeling may leave the Group exposed to unanticipated risks relating to certain perils or geographic regions, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

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In the event of a catastrophic event, actual losses of the Group could be substantially different from the losses estimated by the Group using catastrophe models.

The Group underwrites a broadly diversified insurance and reinsurance portfolio across a wide range of risk classes that members of Fidelis MGU’s management have successfully underwritten in the past, including property, energy, marine, aviation, political risk, credit and surety and various others, as well as whole account quota shares. There can be no assurance that the Group will not suffer losses from one or more catastrophic events in any one given geographic zone due to several factors, including the inherent uncertainties in estimating the frequency and severity of such events, potential inaccuracies and inadequacies in the data provided by clients and brokers, the limitations and inaccuracies of modeling techniques, the limitations of historical data used to estimate future losses or as a result of a decision to change the percentage of the shareholders’ equity exposed to a single modeled catastrophic event. The Group’s estimated probable maximum loss is determined through the use of modeling techniques, but such estimate does not represent the Group’s total potential loss for such exposures.

Catastrophe modeling is a relatively new discipline that utilizes a mix of historical data, scientific theory and mathematical methods. There is considerable uncertainty in the data and parameter inputs for (re)insurance industry catastrophe models. In that regard, there is no universal standard in the preparation of insured data for use in the models and the running of modeling software. The accuracy of the models depends heavily on the availability of detailed insured loss data from actual large catastrophes. Due to the limited number of events and the fact that no two events are precisely the same, there is significant potential for substantial differences between the modeled loss estimate and actual Group experience for a single large catastrophic event.

This potential difference could be even greater for perils without recent loss experience, including natural catastrophe risks such as U.S. earthquakes, or less developed modeled annual severity, such as European windstorms, as well as man-made risks, such as cyber-attacks. Cyber is an example of a peril in respect of which modeling is not yet very developed. In addition, even though wildfires in California and along the western coast of the United States have increased in frequency over recent years, the wildfire models are not as developed as those for peak insured risks.

The Group relies upon Fidelis MGU’s catastrophe modeling, which in turn relies upon third-party estimates of industry insured exposures. There could be significant variation between the Group’s actual losses and those of the industry following a catastrophic event. In addition, actual losses may increase if the Group has reinsured some or all of its exposures and its reinsurers fail to meet their obligations or the reinsurance protections purchased are exhausted or are otherwise unavailable.

The Group has direct and indirect exposure to substantial insured losses resulting from catastrophic events. The Group is exposed to natural catastrophes such as hurricanes, earthquakes, typhoons, floods, sea surges, fire and severe weather patterns occurring in one or more of the countries in which the Group operates or globally, as well as to human-instigated catastrophic events of terrorism, cyber-attack, war or nuclear-related events and to systemic events such as a global economic crisis. The Group is also exposed to perils that are highly influenced by a combination of natural processes and man-made factors, such as epidemics and pandemics. The predictability, severity, frequency and post-event estimation of such varied events are extremely difficult to assess, under existing models or otherwise. In addition, Fidelis MGU only utilizes industry catastrophe modeling in relation to natural catastrophes and, therefore, the Group’s exposure to human-instigated catastrophic events is less well modeled and may be subject to greater uncertainty. Any failures or limitations of models or incorrect estimations by Fidelis MGU could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group’s losses may exceed its loss reserves or available liquidity at any time, which could significantly and negatively affect the Group’s business.

The Group’s results of operations and financial condition depend upon its ability to assess accurately the potential losses associated with the risks that it insures and reinsures and the sufficiency of reserves. Reserves are

34

estimates at a given time of what an insurer or reinsurer ultimately expects to pay on claims, based on facts and circumstances then known, predictions of future events, estimates of future trends in claim frequency and severity and other variable factors such as inflation.

The inherent uncertainties of estimating loss reserves generally are greater for reinsurance business compared to insurance business, primarily due to:

• the significant lapse of time from the occurrence of the event to the reporting and ultimate resolution or settlement of the claim for certain lines of business;

• the diversity of development patterns among different types of reinsurance treaties or facultative contracts; and

• the necessary reliance on the ceding insurer for information regarding claims.

The Group’s estimations of reserves (including those based on input from Fidelis MGU) may be unreliable. Actual losses and loss adjustment expenses paid may deviate, perhaps substantially, from the estimated loss reserves and loss expense reserves contained in its financial statements. Going forward, if the Group’s loss reserves are determined to be inadequate, the Group will be required to increase its loss reserves with a corresponding reduction in net income in the period in which the Group identifies the deficiency. There can be no assurance that the Group’s claims will not exceed its loss reserves or loss expense reserves which may significantly and negatively affect the Group’s business for such period and beyond.

The Group’s operating results may be adversely affected by an unexpected accumulation of attritional losses.

In addition to the Group’s exposures to catastrophes and other large losses as discussed above, the Group’s operating results may be adversely affected by unexpectedly large accumulations of attritional losses (i.e., relatively smaller losses arising frequently in the ordinary course of (re)insurance business operations, excluding major losses). The Group seeks to manage this risk by setting out appropriate underwriting parameters and risk tolerances in the Group Annual Plan and in each Subsidiary Annual Plan (each, as defined below; see “Material Contracts and Related Party Transactions—Framework Agreement—Subsidiary Annual Plans”) to guide the pricing, terms and acceptance of risks by Fidelis MGU on behalf of Current Fidelis. These parameters, which may include pricing models, are intended to ensure that premiums received are sufficient to cover the expected levels of attritional losses and a contribution to the cost of catastrophes and large losses where necessary. However, it is possible that the Group’s underwriting approaches or the pricing models on which the Group relies may not work as intended or may not capture all sources of potential loss and that actual losses from a class of risks may be greater than expected. These pricing models are also subject to the same limitations as the models used to assess the Group’s exposure to catastrophe losses discussed above. Accordingly, these factors could adversely impact the Group’s business, prospects, financial condition or results of operations.

The failure of any risk management and loss limitation methods the Group employs could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group employs various risk management and loss limitation methods, including purchasing reinsurance and sponsoring catastrophe bond transactions. The Group seeks to mitigate its loss exposure by writing a number of insurance and reinsurance contracts on an excess of loss basis, such that the Group only pays losses that exceed a specified retention. The Group also seeks to limit certain risks, such as catastrophes and political risks, by geographic diversification. Geographic zone limitations involve significant underwriting judgments, including the determination of zone boundaries and the allocation of policy limits to zones. In the case of proportional (also known as pro rata) property reinsurance treaties, the Group may seek per occurrence limitations to limit the impact of losses from any one event, although the Group may not be able to obtain such limits in certain markets, in which case such treaties may not include any such caps. Various provisions in the Group’s policies intended to limit its risks, such as limitations or exclusions from certain coverage and choice of forum, may not always be

35

enforceable. The various loss limitation methods that the Group employs may not respond in the way intended due to the nature of the loss events arising in any given period, as well as disputes relating to coverage terms, exclusions, counterparty credit risk or risks relating to the use of differing basis for loss estimations. For additional information regarding reinsurance and catastrophe bonds, see “Business—Outwards Reinsurance or Retrocessional Coverage.” The Group cannot guarantee that any of these loss limitation methods will be effective or that disputes relating to coverage will be resolved in the Group’s favor. The failure of any risk management and loss limitation methods the Group employs could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group’s retrocessional coverage may be exhausted if a large number of claims occur.

The Group has in place various retrocessional reinsurance contracts protecting the Group’s different business segments. See “Business—Outwards Reinsurance or Retrocessional Coverage.” In many cases these contracts provide, following a first loss, for one or more reinstatements of the limit recoverable under the contract with such reinstatements sometimes dependent on payment of additional premiums. The Group purchases aggregate coverage contracts, which provide the Group with retrocessional coverage if losses on the relevant business exceed a given attachment point. The Group also seeks outwards retrocessional protection by accessing the capital markets directly through catastrophe bond sponsorship such as the four Herbie Re Ltd. (“Herbie Re”) catastrophe bonds sponsored by the Group and discussed elsewhere in this prospectus, which provide for multi-year coverage.

However, if several large losses occur or large losses develop adversely, the Group may exhaust portions or the entirety of its outwards retrocession program. Furthermore, the Group cannot be sure that additional retrocessional coverage will continue to be available to it on acceptable terms, or at all. The Group’s risk exposure will be materially greater due to higher loss limits and less risk diversity, and the Group’s underwriting capacity will therefore be restricted, if it cannot purchase adequate retrocessional coverage.

If actual renewals of the Group’s existing policies and contracts do not meet expectations, the Group’s GPW in future fiscal periods and its business, prospects, financial condition or results of operations could be materially adversely affected.

Many of the Group’s insurance policies and reinsurance contracts are for a one-year term (in particular, across its property reinsurance lines and Specialty segment). The Group makes assumptions about the renewal rate and pricing of its prior year’s policies and contracts in its financial forecasting process. If actual renewals do not meet commercial expectations or Fidelis MGU does not renew contracts, the Group’s GPW in future fiscal periods and its future operating results and financial condition could be materially adversely affected.

In addition, irrespective of the renewal terms, the Group may fail to renew or obtain new insurance or reinsurance business at the desired or profitable rates or at all. There can be no assurance that business will be available to Fidelis MGU for the benefit of the Group on terms or at prices that it considers to be attractive and there cannot be any assurance that if such terms or prices exist at present, they will continue as policies renew. Any failure to renew insurance or reinsurance contracts that are material and profitable to the Group could adversely impact the Group’s business, prospects, financial condition or results of operations.

The Group’s business, prospects, financial condition or results of operations will fluctuate in line with the (re)insurance industry cycle, and the Group expects to experience periods with excess underwriting capacity and unfavorable premium rates and policy terms and conditions, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group’s financial performance may be expected to fluctuate in line with the (re)insurance industry’s cyclical patterns characterized by periods of significant competition in pricing and underwriting terms and conditions, which is known as a “soft” insurance market, followed by periods of lessened competition and increasing premium rates, which is known as a “hard” insurance market.

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The insurance and reinsurance pricing cycle has historically been a market phenomenon, driven by supply and demand rather than by the actual cost of coverage. The supply of insurance and reinsurance is determined by prevailing prices, the level of insured losses and the level of industry capital surplus which, in turn, may fluctuate, including in response to changes in rates of return on investments being earned in the (re)insurance industry, which are outside of the control of the Group. The upward phase of a cycle was often triggered when a major event or series of events forced insurers and reinsurers to make large claim payments, thereby drawing down capital. This, combined with increased demand for insurance against the risk associated with the event, pushed prices upwards. In the period prior to 2018, the industry had seen a market characterized by increasing surplus capital and relatively lower premium rates, which, in turn, had led to depressed pricing across certain of the Group’s lines of business for a sustained period since its inception. Hurricanes Florence and Michael, Typhoons Jebi, Mangkhut and Trami and the California wildfires in 2017 and 2018 led to a modest upward trend in pricing for January 2019 renewals across certain lines of business. In line with expectations, the Group experienced a further hardening of markets at subsequent renewal dates across certain lines of business as a result of increased frequency of catastrophe events, including Hurricanes Dorian, Laura, Sally, Ida and Ian, Typhoons Faxai and Hagibis, the 2020 California wildfires, Winter Storm Uri, Storm Bernd which caused widespread European floods, and industry losses from the COVID-19 pandemic, as well as other factors affecting capacity availability such as the Lloyd’s Decile-10 review or the Ukraine Conflict.

Although an individual (re)insurance company’s financial performance is dependent upon its own specific business characteristics, the profitability of most (re)insurance companies tends to follow this cyclical market pattern, with profitability generally increasing in hard markets and decreasing in soft markets.

Insurers and reinsurers, such as the Group, have experienced significant fluctuations in operating results due to competition, frequency of occurrence or severity of catastrophic events, levels of underwriting capacity, underwriting results of primary insurers, general economic conditions and other factors. Although the Group does not compete entirely on price or targeted market share, negative market conditions may impair the Group’s ability to write insurance at rates that it considers appropriate relative to the risk assumed. If the Group cannot write insurance at appropriate rates, this could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

At present, the Group believes that the market remains “hard” and expects such “hard” market to continue for the subsequent 2023 renewals. As a result, rates in particular lines of business will continue to present opportunities for the Group, particularly in the Specialty segment and across a number of property lines of business. This belief as to anticipated industry rates is based on the Group’s own expertise and opinions of the (re)insurance industry commentators and constitutes a forward-looking statement. All forward-looking statements rely on a number of assumptions concerning future events and are subject to a number of uncertainties and other factors, many of which are outside of the control of the Group and other parties and which could cause actual results to differ materially from such forward-looking statements. In addition, there can be no certainty as to how long these market conditions will last and the cycle may fluctuate as a result of changes in economic, legal, political and social factors, including the ongoing Ukraine Conflict and the impact of sanctions imposed on Russia. See “—Risks Relating to Recent Events—The full extent of the impacts of the ongoing Ukraine Conflict on the (re)insurance industry and on the Group’s business, financial condition and results of operations, including in relation to claims under the Group’s (re)insurance policies, are uncertain and remain unknown.” Since cyclicality is due in large part to the collective actions of insurers and reinsurers, general economic conditions and the occurrence of unpredictable events, the Group cannot predict or control the timing or duration of changes in the market cycle, including how long any favorable market conditions will persist. If the Group fails to manage its business appropriately through the cyclical nature of the (re)insurance industry, its business prospects, operating results or financial condition could be materially adversely affected.

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The business written by the Group, particularly in its Bespoke and Specialty segments, is vulnerable to global economic and geopolitical uncertainty.

A portion of the Group’s business focuses on bespoke (re)insurance underwriting for tailored coverage, which we refer to as the Bespoke pillar. Business in the Group’s Bespoke pillar includes policies covering credit and political risk, political violence and terrorism, cyber, title, transactional liabilities, mortgage and other bespoke products that fit our criteria. These and other lines of business composed of the Bespoke pillar are particularly susceptible to severe economic downturns or seismic shocks, which could trigger significant losses for this particular area of business compared to business composed of the Group’s other (re)insurance business which typically responds to the insurance cycle described above rather than the economic cycle.

The Group saw a general drop in bespoke (re)insurance underwriting deal flow throughout 2020 due to the COVID-19 pandemic. As the economies around the world began to recover, in 2021 the Group saw a higher market appetite for the underlying transactions that these products cover and is cautiously anticipating a continued level of appetite through 2023, subject to economic uncertainty, inflation pressures and monetary actions, the ongoing Ukraine Conflict and the impact of sanctions imposed on Russia. However, to the extent there is further disruption from such public health, economic and geopolitical factors, there may be further delays and uncertainties in relation to those underlying transactions, which could lead to further reductions to deal flow within the Bespoke pillar. Despite the Group’s current focus on the Specialty segment discussed below, given the historic size of the Bespoke pillar relative to the Group’s wider business, prolonged periods of global economic uncertainty, could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Another portion of the Group’s business, which we refer to as the Specialty pillar, focuses on traditional specialty business lines such as aviation, energy, space, marine, contingency and property D&F. The underlying industries to which the Group’s Specialty segment business lines relate, such as marine, energy and in particular aviation, have faced unprecedented challenges resulting in loss of profits, government-imposed restrictions, and a general downturn in business due to recent global economic uncertainty. Despite the Specialty segment historically being our smallest segment due to the historic rating environment, the rates available in certain Specialty classes increased throughout 2020, 2021 and 2022, and have continued to do so in 2023 to date, resulting in a significant increase in GPW attributable to our Specialty segment.

However, given the recent market volatility and ongoing uncertainty resulting from the global economic and geopolitical uncertainty, the Group might be unable to continue its strong growth in Specialty. Additionally, since the onset of the ongoing Ukraine Conflict, the aviation line of business has come under particular strain arising from the indirect impact of sanctions imposed on Russia and western leased aircraft currently located in Russia. Given the novelty of the situation, it is impossible to determine whether and how potential losses may crystallize, which will ultimately depend on multiple interlocking dependencies, including the future behavior of the Russian government and airlines, the interpretation of the coverages in place and the way in which sanctions are interpreted. The spread of possible ultimate outcomes is huge, with scope for scenarios where Russian behavior and/or sanctions mean that no claims emerge, and others in which the (re)insurance market would face its largest ever non-natural catastrophe. As both segments are potentially susceptible to changes in economic activity, any significant and continued economic downturn may impact the Group’s Bespoke and Specialty segments and the Group’s GPW, as well as have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Any future acquisitions, strategic investments or new platforms could expose the Group to further risks or turn out to be unsuccessful.

From time to time, and subject to the Framework Agreement (as defined below, see “Material Contracts and Related Party Transactions—Framework Agreement”) and each respective Delegated Underwriting Authority Agreement, the Group may pursue growth through acquisitions and strategic investments in businesses

38

or new underwriting, insurance-linked securities (“ILS”) or marketing platforms. The negotiation of potential acquisitions or strategic investments as well as the integration of an acquired business, personnel or underwriting or marketing platforms (including raising alternative capital from reinsurance sidecar finance structures (“sidecars”)) could result in a substantial diversion of management resources and the emergence of other risks, such as potential losses from unanticipated litigation, a higher level of claims than is reflected in reserves, loss of key personnel in acquired businesses or an inability to generate sufficient revenue to offset acquisition costs.

The Group’s ability to manage its growth through acquisitions, strategic investments or new or alternative platforms (including sidecars) will depend, in part, on its success in addressing such risks. While the Group is not currently contemplating any such acquisitions or strategic investments, the Group’s nimble approach to capital management based on opportunities presented and sought out means that the Group may opportunistically from time to time pursue such acquisitions, new platforms or strategic investment strategies. Any failure by the Group to implement its acquisitions, new platforms or strategic investment strategies effectively could have a material adverse effect on its business, prospects, financial condition or results of operations.

Competition within the industry may make profitable pricing difficult and the Group may fail to be able to access profitable insurance or reinsurance business.

The insurance industry is highly competitive. In its underwriting activities, the Group may find itself in competition with other insurers and reinsurers that may have an established position in the market or greater financial, marketing and management resources available to them. Competition in the types of business that the Group may underwrite is based on many factors, including premiums charged and other terms and conditions agreed, services provided, financial strength ratings assigned by third-party credit rating agencies and perceived financial strength, speed of claims payment, reputation and experience in the line of business to be written, and continuity, strength of relationship and reputation with clients and brokers. Competition can adversely affect premium levels, including on business written by the Group, by increasing insurance industry capacity, reducing prices in response to favorable loss experience, affecting the pricing of underlying direct coverage and other factors, any of which can develop in a relatively short period of time. In addition, the Group cannot predict the extent to which competition from new competitors (including managing general agents, hedge funds, capital markets products such as catastrophe bonds and new underwriting companies that provide similar products) or existing competitors raising equity, debt or ILS capital could increase (re)insurance capacity and depress premium rates. There may be a divergence of views among market participants on the likely duration and extent of rate improvements, if and when anticipated. Increased competition could result in fewer submissions, lower premium rates or less favorable policy terms and conditions with respect to the Group’s products, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Consolidation in the (re)insurance industry could adversely impact the Group’s business and results of operations.

Recent years have seen increased consolidation and convergence among companies in the (re)insurance industry resulting in increasingly larger and more diversified competitors with greater capitalization than the Group. As evidenced by merger and acquisition transactions in recent years, the consolidation trend may continue and even accelerate in the near future, which may lead to increased competitive pressure in the Group’s business lines from such competitors. In addition, as companies consolidate, the resulting change in the competitive landscape may impact the Group’s ability to attract the most talented insurance professionals and to retain and incentivize its existing employees. Any of these risks relating to consolidation within the industry could adversely affect the Group’s insurance and reinsurance businesses, prospects, financial condition or results of operations.

As the (re)insurance industry consolidates, the cost, capital and (re)insurance synergies and combined underwriting leverage resulting from consolidation may mean a larger global (re)insurer is able to compete more effectively and also may be more attractive to brokers and agents looking to place business than the Group. These

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consolidated competitors may try to use their enhanced market power to obtain a larger market share through increased line sizes. Larger (re)insurers also may have lower operating costs and an ability to absorb greater risk while maintaining their financial strength ratings, thereby allowing them to price their products more competitively without impacting rating. If competitive pressures reduce rates or negatively affect terms and conditions considerably, the Group may reduce its future underwriting activities in those lines thus resulting in reduced premiums and a potential reduction in expected earnings.

As the (re)insurance industry consolidates, competition for customers may also become more intense and the importance of properly servicing each customer will increase. Several of the mergers of (re)insurers that compete with the Group were partially driven by strategic plans to write more (re)insurance business. The Group could therefore incur greater expenses relating to customer acquisition and retention, reducing the Group’s operating margins. In addition, (re)insurance companies that merge may be able to spread their risks across a consolidated, larger capital base so that they require less outwards reinsurance than the Group. Furthermore, such (re)insurance companies may, as a result of consolidation, purchase less reinsurance and retrocession cover from the Group than they currently do.

There has been a similar trend of increased consolidation of agents and brokers in the (re)insurance industry. As most of the Group’s products are distributed by Fidelis MGU through agents and brokers, consolidation could impact relationships with, and fees paid to, some agents and brokers. Consolidation of distributors may also increase the likelihood that distributors will try to renegotiate the terms of existing selling agreements to terms less favorable to the Group. As brokers merge with or acquire each other, any resulting failure or inability of brokers to market the Group’s products successfully, or the loss of a substantial portion of the business sourced by one or more of the Group’s key brokers, could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group may not be able to write as much premium as expected in the Group Annual Plan with the desired level of projected profitability.

The Group may not write as much premium as expected with the desired level of profitability. Factors which may inhibit or preclude the Group from obtaining the participations on desirable business sufficient to meet the projected premium or profitability levels include, among others:

• the failure of Fidelis MGU to maintain successful relationships with clients, brokers and other intermediaries to distribute the Group’s products;

• insurance and reinsurance pricing not responding positively as has happened in the past to a significant loss event;

• continued willingness by other market participants to underwrite insurance and reinsurance business at rates, terms or conditions that are at best marginally profitable and are more attractive to customers than the Group is prepared to price at;

• difficulty penetrating existing program structures due to established relationships between such cedants (or their intermediaries) and reinsurers, or clients (or their intermediaries) and their insurers on programs desired by the Group;

• intermediaries entering into bilateral or facility arrangements with single carriers or markets, where previously the business was more widely available; and

• possible unwillingness of prospective cedants (or their intermediaries) or clients (or their intermediaries) to accept the Group’s participations based on competitors’ higher ratings or concerns regarding the Group’s investors’ time horizons and possible exit strategies or ability to maintain its financial strength ratings.

If the Group is not able to write as much increased business as expected, or at the projected levels of profitability, it may write a lesser volume of business and/or write business at lower projected levels of

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profitability. This could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Industry-wide developments could adversely affect the Group’s business.

The availability and price of insurance and reinsurance coverage has been affected by factors such as the global economic recession, stock market performance, interest rates, high inflationary environment and the occurrence of global catastrophic events. Recent examples of the latter are Hurricanes Florence, Dorian, Michael, Laura, Sally, Ida and Ian, Typhoons Faxai, Hagibis, Jebi, Mangkhut and Trami, the U.S. Midwest derecho, Winter Storm Uri, the California wildfires in recent years and Storm Bernd, which caused widespread European floods, and the COVID-19 pandemic, as well as the ongoing Ukraine Conflict. Volatility in regional and global economic growth has the potential to reduce the number and the amount of GPW in the Group’s business lines such as marine, where such volatility may result in a decline in shipbuilding projects, and aviation lines in the event of a significant reduction in passenger volumes and departures.

Within energy lines, the recent rally in oil prices, brought around by fears of supply issues in light of the ongoing Ukraine Conflict, affects asset prices and may impact on existing and future exploration and extraction projects, also producing broader financial distress within the energy industry. Although Russian energy exports are continuing, the Western nations are exploring their options and seeking alternative energy sources. The Organisation for Economic Cooperation and Development (the “OECD”) nations responded to the crisis by releasing more barrels from their strategic reserves, which was aimed at stabilizing the prices. Although this move has generally been welcomed, there is no guarantee that it will impact oil prices in any meaningful way as this unprecedented economic and political situation has not been fully modeled yet and the prices are expected to remain extremely volatile. This dynamic in the energy sector may result in increased demand for insurance but limits (particularly in respect of business interruption) may be higher.

Fluctuations in demand for insurance and reinsurance products or over-or under-supply of capacity can result in governmental intervention in the insurance and reinsurance markets, which may affect the risks which may be available for the Group to consider underwriting, or render terms and pricing unattractive. At the same time, threats of further terrorist attacks and political unrest in Europe, the Middle East, North Africa, the U.S., Australasia and Asia, and continued uncertainty arising directly and indirectly from the recent turbulence in the global financial markets, have adversely affected general economic, market and political conditions, increasing many of the risks associated with the Group’s business worldwide. See “—Risks Relating to Recent Events.”

A downgrade or withdrawal of, or other negative action relating to, the Group’s financial strength rating(s) by insurance rating agencies could adversely affect the volume and quality of business presented to the Group.

Third-party credit rating agencies assess and rate the financial strength of insurers and reinsurers based upon criteria established by those rating agencies. The claims-paying ability ratings assigned by rating agencies to insurance and reinsurance companies represent independent opinions of financial strength and the ability to meet policyholder or other obligations. Ratings reflect the rating agencies’ respective opinions on the ability of the Group to pay claims and are not evaluations directed to investors in, and are not recommendations to buy, sell or hold, the Group’s securities. Insureds, cedants and intermediaries use these ratings as one measure by which to assess the financial strength and quality of insurers and reinsurers. These ratings are often a key factor in the decision by an insured, cedant or an intermediary on whether and in what quantum to place business with a particular insurance or reinsurance provider. Many insureds, cedants and intermediaries maintain a listing of acceptable insurers or reinsurers, generally based upon credit ratings.

Prior to the Separation Transactions, the Group was assigned an “A” (Excellent) financial strength rating by A.M. Best, the third-highest of 13 rating levels, with a stable outlook on all entities. A.M. Best’s ratings range from “A+” to “D.” Each A.M. Best rating category from “A+” to “C” may be designated either an additional plus (+) or a minus (-) sign as a rating notch that reflects a gradation of financial strength within the rating

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category. Additionally, A.M. Best assigned a “BBB” long-term issuer credit rating to FIHL, which indicates a good ability to meet ongoing senior financial obligations and a financial strength rating of “A” (Excellent) and the long-term issuer credit rating of “A” (Excellent) to FIBL, FUL and FIID. In connection with the Separation Transactions, the Group completed a rating evaluation service with A.M. Best, following which, A.M. Best had placed “under review with negative implications” the ratings assigned to FIHL, including the Group’s financial strength rating of “A.” On February 3, 2023, A.M. Best removed from “under review with negative implications” and affirmed the financial strength rating of “A” (Excellent) and the long-term issuer credit rating of “A” (Excellent) of FIBL, FUL and FIID. In addition, A.M. Best removed from “under review with negative implications” and affirmed the long-term issuer credit rating of “BBB” (Good) of FIHL. The outlook assigned to these ratings remained negative at such date. The negative outlooks acknowledge that A.M. Best has noted that it will continue to monitor the Group’s market presence as well as subsequent operating performance now that the Separation Transactions have been consummated.

Prior to the Separation Transactions, the Group was assigned an “A-” financial strength rating by S&P, with a positive outlook, which indicates strong capacity to meet financial commitments but somewhat more susceptibility to the adverse effects of changes in circumstances and economic conditions than those in higher-rated categories. S&P’s ratings range from “AAA” to “D.” Each S&P rating category from “AA” to “CCC” may be modified by the addition of a plus (+) or minus (-) sign to show relative standing within the rating categories. Additionally, S&P has assigned a “BBB” long term issuer rating to FIHL, which indicates adequate capacity to meet financial commitments but greater susceptibility to adverse economic conditions. In connection with the Separation Transactions, the Group completed a rating evaluation service with S&P, following which, S&P had placed under review the ratings assigned to FIHL, including the Group’s financial strength rating of “A-.” On August 5, 2022, S&P affirmed the Group’s ratings, including the “A-” financial strength rating assigned to the Group and a “BBB” long term issuer rating to FIHL, but revised its outlook from positive to stable for all entities. Despite the revision, S&P expressed confidence in the Group’s future operating earnings and strong capital position, noting in particular the Group’s underwriting outperformance of peers between 2017 and 2022.

Following the announcement of the Separation Transactions, on August 1, 2022, Moody’s assigned a “Baa2” long-term issuer rating to FIHL and “A3” insurance financial strength ratings to FIBL, FUL and FIID. The outlook for FIHL is stable. Moody’s generic rating classifications range from “Aaa” to “C.” Each Moody’s generic rating classification from “Aa” to “Caa” may be modified to append numerical modifiers 1, 2, or 3 to show relative position within the rating categories.

A.M. Best, S&P and Moody’s will periodically review the Group’s rating and may revise it downward or revoke it at their sole discretion, based primarily on their analysis of the Group’s balance sheet strength, operating performance and business profile. Factors that may affect such an analysis include:

• if the Group changes its business practice from the Group Annual Plan in a manner that no longer supports its rating;

• if unfavorable financial or market trends impact the Group;

• if the Group’s actual losses significantly exceed its loss reserves;

• if the Group is unable to obtain and retain key personnel;

• if the Group’s investments incur significant losses; and

• if either A.M. Best or S&P alters its capital adequacy assessment methodology in a manner that would adversely affect the Group’s rating.

An actual or anticipated downgrade or revocation of the Group’s financial strength rating, or an announcement that the Group’s financial strength rating is under review or other negative action by a rating agency, could provide certain customers with a right to terminate their (re)insurance contracts with the Group

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and would adversely affect the volume and quality of business presented to the Group and could potentially have a negative effect on the Group’s financial condition and results of operations. A downgrade is also a basis for termination of the Framework Agreement by Fidelis MGU, subject to a cure period. A downgrade could also potentially impact the Group’s existing letter of credit facilities by triggering a covenant breach, which would have a negative effect on the Group’s business.

Additionally, third-party credit rating agencies may increase the levels of capital they require an insurer or reinsurer to hold in order to maintain a certain credit rating. Such changes could result in the Group having to raise additional capital or purchase reinsurance in order to maintain its credit rating. The availability and cost of additional financing or capital depends on a variety of factors, including our credit ratings and credit capacity. If the Group does not raise such additional capital or purchase suitable reinsurance, that could result in a downgrade of its credit rating, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

A downgrade in rating could have a material effect on the Group’s ability to write business or to maintain business already written and would adversely affect the Group’s competitive position in the insurance and reinsurance industries and make it more difficult to market its products. A downgrade could, therefore, result in a substantial loss of business as insureds, ceding companies, agents and brokers that place business with the Group companies might move to other insurers and reinsurers with higher ratings or insist on less favorable terms as a condition of continuing to do business. A credit rating downgrade might also give rise to a right of termination or amendment of the Group’s credit facilities. While there can be no assurance that increased levels of capital will not be required in the future, the rating agencies have not made the Group aware of any such increase as part of the rating evaluation service in connection with the Separation Transactions.

Changing climate conditions and under-developed catastrophe modeling tools could lead to worse than expected losses and may adversely affect the Group’s operating results, financial condition, profitability or cash flows.

Multiple years of above-average temperatures and drought, poor forest management, and widespread development in the zone between wild land and human development have proved a dangerous combination. The catastrophe modeling tools that insurers and reinsurers use to help manage catastrophe exposures are based on assumptions and judgments that rely on historical trends, are subject to error and may produce estimates that are materially different from actual results. Changing climate conditions could cause catastrophe models to be even less accurate, which could limit the Group’s ability to effectively manage its exposures, in particular to perils for which modeling is under-developed, such as wildfires and flooding. Failures or inadequacies in modeling relating to climate change could result in the Group’s results of operations or financial condition differing materially from the Group’s expectations or any related projections.

The failure to appreciate and respond effectively to the trends and risks associated with ESG initiatives and factors could adversely affect the Group’s relationship with stakeholders and its achievement of the Group Annual Plan.

The purpose of a business and the way in which it operates in achieving its objectives, including in relation to ESG matters, are an increasingly material consideration for the Group’s key stakeholders in achieving their own ESG objectives and aims. The Group has seen increased focus and scrutiny on ESG-related matters from its key stakeholders, such as its institutional investors, policyholders, employees and suppliers, as well as policymakers, regulators, rating agencies, industry organizations and local communities, which could lead to a change in approach to ESG for the Group and in the general (re)insurance industry as a whole. ESG-related initiatives, trends and risks may directly or indirectly impact the Group’s business and the achievement of the Group Annual Plan and consequently those of its key stakeholders. A failure to transparently and consistently implement an ESG strategy, in its key markets and across operational, underwriting and investment activities, may adversely impact the Group Annual Plan, financial results and reputation of the Group and may negatively

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impact relationships with the Group’s stakeholders, all of whom have expectations, concerns and aims related to ESG matters which may differ from the Group’s. See “Business—Our Commitment to Environmental, Social and Governance Matters.”

Changes in law relating to certain perils could adversely affect the Group’s business.

A change in law relating to certain perils for which the Group writes insurance or reinsurance may have a significant impact on the Group’s ability to respond to certain events, including the manner and time frame for processing claims, the development of claim severity or the interpretation of the underlying policies. For example, in response to several wildfire events affecting California homeowners, the state has enacted new insurance consumer protection laws for California policyholders that took effect on January 1, 2019 and require insurers to afford certain policy protections to California insureds for future wildfire events. Such changes in law and practice in response to the recent wildfire events, as well as other changes in law and practice relating to other perils for which the Group writes insurance or reinsurance, may have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Outwards reinsurance is a key part of the Group’s strategy, subjecting the Group to the credit risk of its reinsurers and may not be available, affordable or adequate to protect against losses.

A key part of the Group’s strategy is to follow the practice of reinsuring and retroceding with other insurance and reinsurance companies and ILS vehicles a portion of the risks under the insurance and reinsurance contracts that it writes in order to protect the Group against the severity of losses on individual claims and unusually serious occurrences in which a number of claims produce a large aggregated loss. Authority to design and place such outwards reinsurance has been delegated to Fidelis MGU. In addition to traditional outwards reinsurance, the Group participates in the catastrophe bond market and has sponsored four series of catastrophe bonds issued by Herbie Re, pursuant to which the Group obtains collateralized retrocessional coverage from capital markets participants. The amount of coverage purchased, either in the traditional or alternative markets, is determined by the Group’s risk strategy together with the price, quality and availability of such coverage. Coverage purchased for one year will not necessarily conform to purchases for another year.

There can be no assurance that the Group will be able to obtain reinsurance or to enter into retrocession arrangements (including by renewing its catastrophe bond transactions) at a price, quality or in the amounts which the Group requires. There can be no assurance that the Group’s outwards reinsurance or retrocession protection will be sufficient for all eventualities, which could expose the Group to greater risk and greater potential loss, which could in turn have a material adverse effect on its business, prospects, financial condition or results of operations. In particular, if a number of large losses occur in any one year, there is a chance that the Group could exhaust its outwards reinsurance and retrocession program. In this event, it is not certain that further reinsurance and/or retrocessional coverage would be available on acceptable terms, or at all, for the remainder of that year or for future years which could materially increase the risks and losses retained within the Group.

In addition, in the event Fidelis MGU cannot arrange to obtain the amount of reinsurance or retrocessional protection for the Group within the parameters set forth in each of the Subsidiary Annual Plans, then the Group may need to reduce the amount of business it writes accordingly in order to remain within its risk tolerances. Such reduction in the availability of reinsurance or retrocessional protection could also have a significant impact on the Group’s capital reserves, by potentially requiring the Group to hold more capital. In particular, under Directive 2009/138/EC (“Solvency II”), which is also transposed into the U.K.’s domestic prudential regime, the relevant operating subsidiaries of the Group are required to have a reasonable expectation that outwards reinsurance will be placeable to future periods.

Collectability of traditional reinsurance and retrocession is dependent upon the solvency of reinsurers or retrocessionaires and their willingness to make payments under the terms of reinsurance or retrocession agreements. In particular, the Group can be exposed to non-coterminous wording risk under such agreements,

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including interpretations by our reinsurers or retrocessionaires that they may withhold payment for losses. As such, the terms and conditions of the reinsurance purchased by the Group may not provide precise cover for the losses the Group incurs on the underlying insurance or reinsurance which it has sold. A reinsurer’s insolvency or inability or unwillingness to make payments under the terms of a reinsurance or retrocession arrangement could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

In the case of the Group’s catastrophe bond and industry loss warranty transactions, collectability is dependent on whether the relevant coverage is triggered. Each of the Group’s catastrophe bond transactions and industry loss warranty transactions to date has utilized an industry loss index trigger, which means that the amount of recoveries paid to the Group is determined by the levels of catastrophe losses to the wider (re)insurance industry rather than by the amount of losses that the Group actually suffers. There can be no guarantee, therefore, that these catastrophe bonds and industry loss warranties will provide adequate protection if the Group’s loss experience does not correlate with losses on an industry-wide basis triggering a payment under the relevant contracts.

The Group is exposed to credit loss in the event of nonperformance by its counterparties on derivative agreements. The Group seeks to further reduce the risk associated with such agreements by entering into such agreements with large, well-established financial institutions. In addition, the U.S. Commodity Futures Trading Commission and other regulators require the Group and its swap dealer counterparties to collect and post initial and variation margin with respect to non-cleared swaps. Any initial margin required to be posted to the Group’s swap dealer counterparties under these rules is segregated with a third-party custodian. However, there can be no assurance that the Group will not suffer losses in the event a counterparty or custodian fails to perform or is subject to a bankruptcy or similar proceeding.

Cyber threats are an evolving risk area affecting not only the specific cyber insurance market but also the liability coverage the Group provides which may adversely affect the Group.

The Group has introduced processes to manage its potential liabilities as a result of specific cyber coverage and other coverage the Group provides to its (re)insurance policyholders, including for the business sourced by Fidelis MGU. However, given that this is an area where the threat landscape is uncertain and continuing to evolve, there is a risk that increases in the frequency and effectiveness of cyber-attacks on the Group’s policyholders could adversely affect (possibly to a material extent) the Group’s business, prospects, financial condition or results of operations. This risk is also dependent on the measures the individual policyholders use to protect themselves to keep pace with the emerging threat, as well as the development and issuance of policy terms and conditions which are reactive to the evolving threat landscape.

The Group may write selected quota share reinsurance policies and assume a share of the liabilities of its underlying reinsureds, which may expose it to certain losses.

The Group may write selected quota share reinsurance policies and also insure a share of the liabilities of its underlying reinsureds. The Group may suffer losses arising from the underlying judgment of the staff of reinsureds, underlying pricing, terms and conditions of the business in which it shares risk, sub-optimal claims management and other business administration shortcomings, poor but not contractually actionable information disclosure, failure to observe underwriting guidelines but not to a contractually actionable extent and unexpected catastrophic exposures in the reinsureds’ own account. These risks are equally applicable to many other types of reinsurance that the Group may write (in addition to quota share reinsurance).

Loss of business reputation or negative publicity could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group is vulnerable to adverse market perception since it operates in an industry where integrity, customer trust and confidence are paramount. In addition, any negative publicity (whether well founded or not)

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associated with the business or operations of the Group could result in a loss of clients and business. Accordingly, any mismanagement, fraud or failure by its employees or employees of Fidelis MGU to satisfy fiduciary responsibilities, or the negative publicity resulting from such activities or any allegation of such activities and consequential loss of reputation, could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. These issues also relate to regulatory conduct risk, for which see “—Risks Relating to Regulation of the Group.”

The Group is exposed to the risk of litigation which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The extent and complexity of the legal and regulatory environment in which the Group operates and the products and services the Group offers mean that many aspects of the business involve substantial risks of liability. Any litigation brought against the Group in the future could have a material adverse effect on the Group. The Group’s insurance may not necessarily cover all or any of the claims that clients or others may bring against the Group or may not be adequate to protect it against all the liability that may be imposed.

The Group also may be involved in litigation against third parties in the normal course of business and the probable outcome of all such litigation may be taken into account in the assessment of the Group’s liabilities. If the outcome of such litigation is incorrectly estimated, this could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Coverage disputes can increase expenses and incurred losses, which could have a material adverse effect on the Group’s business.

There can be no assurance that various provisions of the Group’s insurance policies and reinsurance contracts, such as limitations on, or exclusions from, coverage, will be enforceable in the manner intended. In particular, the ongoing Ukraine Conflict may lead to coverage disputes in relation to, among others, policy language, the impact of sanctions or cancellation notices. Such actions have led to an increase in the risk of uncertainty surrounding emerging claims. See “—Risks Relating to Recent Events.”

This increased risk adds further pressure to an already uncertain area surrounding emerging claims, which has been particularly prominent in the Florida insurance market, which has seen an increase in losses and loss adjustment expenses due to the prevalence of assignment of benefits (“AOB”) claims. Through AOB, homeowners are increasingly assigning the benefit of their insurance recovery to third parties (including the right to claim back legal fees if they are successful in arguing for a larger than initially offered pay-out). AOB practice in Florida has been characterized by an inflated size and number of claims, increased litigation, interference in the adjustment of claims and the assertion of bad faith actions and one-way attorney fees. There were a large number of AOB claims following Hurricane Irma in 2017, a trend which continued in the wake of Hurricane Michael in 2018. In an effort to stem rising premiums caused by unnecessary litigation and AOB abuse and to curtail any further exponential growth in AOB litigation, Florida’s state legislature has signed into law an AOB reform measure, which will, among other provisions, restrict attorney fees on AOB litigation and allow providers to sell AOB exempt policies. However, until the effects of the new legislation become clear, ongoing AOB activity and related potentially fraudulent claims activity may have a material effect by inflating the size of the Group’s losses and loss adjustment expenses.

Furthermore, as the Group writes a substantial amount of property D&F across the United States, it is exposed to the risk of emerging “bad faith” claims, which have recently been successfully brought in several U.S. states. Such claims are not insurer friendly and especially so when the insurer is a non-U.S. insurer. Additionally, due to potential unfamiliarity with the local rules and regulations, a non-U.S. insurer, such as the Group, runs an increased risk of clerical and logistical errors in getting claims and litigation filings in the United States done on time to allow it to respond in a timely manner before a summary judgment is held against it.

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Although disputes relating to coverage and choice of legal forum can be expected to arise in the ordinary course of the Group’s business, particularly if loss claims are material, the rise in the number of AOB and “bad faith” claims or other coverage disputes could lead to the Group facing a higher volume of claims or quantum of losses than it faced historically. As a result, the Group may incur losses beyond those that it considered might be incurred at the time of underwriting the insurance policy or reinsurance contract, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

We have identified material weaknesses in our internal control over financial reporting and may identify additional material weaknesses in the future or fail to maintain an effective system of internal control over financial reporting, which may result in material misstatements of our consolidated financial statements or cause us to fail to meet our periodic reporting obligations.

In connection with the preparation of our consolidated financial statements for the year ended December 31, 2022, we identified material weaknesses in our internal control over financial reporting. A “material weakness” is a deficiency, or a combination of deficiencies, in internal control over financial reporting such that there is a reasonable possibility that a material misstatement of our annual or interim consolidated financial statements will not be prevented or detected on a timely basis. The material weaknesses were identified in the following areas: (i) the design and operating effectiveness of controls over the secondary review of the accuracy of data input in the policy administration system impacting recording of premiums and acquisition costs, (ii) the necessary resources to consider on a timely basis the application of U.S. GAAP accounting principles where complex accounting judgment exists, and (iii) the design of controls over the completeness and accuracy of reinsurance balances recoverable and payable.

To remedy our identified material weaknesses, we are in the process of adopting several measures intended to improve our internal control over financial reporting. These include strengthening our finance, operations and information technology teams, and implementation of further policies, processes and internal controls relating to our financial reporting. Specifically, those ongoing remediation include the following:

• We have, and will continue to, strengthen our operational resources within the underwriting team to implement additional controls over data input in addition to having expanded the operations team through the provision of specialist third-party resources to assist with data input. Furthermore, in the third quarter of 2022 we engaged a third-party service provider to conduct independent quality control checks over the data in the policy administration system.

• We have strengthened the reinsurance team by hiring additional accounting and operational resources to help ensure that we have sufficient personnel with skills and experience commensurate with the size and complexity of the organization, who can effectively design and execute our process level controls around reinsurance balances payable and recoverables. We will also be implementing additional technology solutions to replace manual processes where possible.

• We have hired additional resources in our Group finance team with knowledge and experience of U.S. GAAP, SEC reporting and internal control over financial reporting.

• Additionally, we have engaged an outside service provider to assist in evaluating and documenting processes and controls, identifying control gaps and strengthening the quality of documentation regarding controls.

We are committed to maintaining a strong internal control environment, and we expect to continue our efforts to ensure the material weaknesses described above and all control deficiencies are remediated. However, these material weaknesses cannot be considered remediated until the applicable remedial controls operate for a sufficient period of time and management has concluded, through testing, that these controls are operating effectively.

We can give no assurance that additional material weaknesses or significant deficiencies in our internal control over financial reporting will not be identified in the future. Our failure to implement and maintain

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effective internal control over financial reporting could result in errors in our financial statements that may lead to a restatement of our financial statements or cause us to fail to meet our reporting obligations. Any failure to implement required new or improved controls, or difficulties encountered in their implementation, could harm our operating results or cause us to fail to meet our reporting obligations. Failure to achieve and maintain an effective internal control environment could cause investors to lose confidence in our reported financial information, which could have a material adverse effect on our Common Share price. Although we are committed to adopting remedial controls, any failure to comply with Section 404 of the Sarbanes-Oxley Act could also potentially subject us to sanctions or investigations by the SEC or other regulatory authorities. Generally, if we fail to achieve and maintain an effective internal control environment, it could result in material misstatements in our financial statements and could also impair our ability to comply with applicable financial reporting requirements and related regulatory filings on a timely basis. As a result, our businesses, financial condition, results of operations and prospects, as well as the trading price of our Common Shares, may be materially and adversely affected. We may also be required to restate our financial statements from prior periods.

We will incur increased costs as a result of operating as a U.S. public company, and our management will be required to devote substantial time to new compliance initiatives and corporate governance practices. We may fail to comply with the rules that apply to public companies, including Section 404 of the Sarbanes-Oxley Act, which could result in sanctions or other penalties that would harm our business.

As a public company that qualifies as a foreign private issuer, we will incur significant legal, accounting, and other expenses that we did not incur as a private company, including costs resulting from public company reporting obligations under the Securities Act of 1933, as amended (the “Securities Act”), the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and regulations regarding corporate governance practices. The Sarbanes-Oxley Act, the Dodd-Frank Wall Street Reform and Consumer Protection Act, the rules of the SEC, the listing requirements of NYSE, and other applicable securities rules and regulations impose various requirements on public companies, including establishment and maintenance of effective disclosure and financial controls and corporate governance practices. We expect that we will need to hire additional accounting, finance, and other personnel in connection with our becoming listed on the NYSE and our efforts to comply with the requirements of being a public company, and our management and other personnel will need to devote a substantial amount of time towards maintaining compliance with these requirements. These requirements will increase our legal and financial compliance costs and will make some activities more time-consuming and costly. For example, these reporting requirements, rules and regulations, coupled with the increase in potential litigation exposure associated with being a public company, could also make it more difficult for us to attract and retain qualified persons to serve on our Board or board committees or to serve as executive officers, or to obtain certain types of insurance, including directors’ and officers’ insurance, on acceptable terms. We are currently evaluating these rules and regulations and cannot predict or estimate the amount of additional costs we may incur or the timing of such costs. These rules and regulations are often subject to varying interpretations, in many cases due to their lack of specificity, and, as a result, their application in practice may evolve over time as new guidance is provided by regulatory and governing bodies. This could result in continuing uncertainty regarding compliance matters and higher costs necessitated by ongoing revisions to disclosure and governance practices. We cannot predict or estimate the amount of additional costs we may incur as a result of becoming a public company or the timing of such costs. Any changes we make to comply with these obligations may not be sufficient to allow us to satisfy our obligations as a public company on a timely basis, or at all.

Pursuant to Sarbanes-Oxley Act Section 404, we will be required to furnish a report by our management on, among other things, our internal control over financial reporting beginning with our second filing of an Annual Report on Form 20-F with the SEC after we become a public company. In order to maintain effective internal controls, we will need additional financial personnel, systems and resources. To achieve compliance with Sarbanes-Oxley Act Section 404 within the prescribed period, we will be engaged in a process to document and evaluate our internal control over financial reporting, which is both costly and challenging. In this regard, we will need to continue to dedicate internal resources, potentially engage outside consultants, adopt a detailed work plan to assess and document the adequacy of internal control over financial reporting, continue steps to improve

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control processes as appropriate, validate through testing that controls are functioning as documented, and implement a continuous reporting and improvement process for internal control over financial reporting. Despite our efforts, there is a risk that we will not be able to conclude, within the prescribed timeframe or at all, that our internal control over financial reporting is effective as required by Sarbanes-Oxley Act Section 404. If we identify one or more material weaknesses, it could result in an adverse reaction in the financial markets due to a loss of confidence in the reliability of our financial statements.

Furthermore, if we identity material weakness in our internal control over financial reporting in the future, we may not detect errors on a timely basis and our financial statements may be materially misstated. We or our independent registered public accounting firm may not be able to conclude on an ongoing basis that we have effective internal control over financial reporting, which could harm our operating results, cause investors to lose confidence in our reported financial information and cause the trading price of our shares to fall. In addition, as a public company we will be required to file accurate and timely reports with the SEC under the Exchange Act. Any failure to report our financial results on an accurate and timely basis could result in sanctions, lawsuits, delisting of our shares from NYSE or other adverse consequences that would materially harm our business and reputation.

The preparation of the Group’s financial statements requires it to make many estimates and judgments that are more difficult than equivalent estimates and judgments made by companies operating outside the (re)insurance sector.

The preparation of the Group’s audited consolidated financial statements and unaudited interim consolidated financial statements requires the Group to make many estimates and judgments that affect the reported amounts of assets, liabilities (including reserves), revenues and expenses and related disclosures of contingent liabilities. The Group evaluates its estimates on an ongoing basis, including those related to premium recognition, insurance and other reserves, reinsurance recoverables, investment valuations, intangible assets, bad debts, impairments, income taxes, contingencies, derivatives and litigation. The Group bases its estimates on market prices, where possible, and on various other assumptions it believes to be reasonable under the circumstances, which form the basis for the Group’s judgments about the carrying values of assets and liabilities that are not readily apparent from other sources.

In particular, estimates and judgments for new (re)insurance lines of business are more difficult to make than those made for more mature lines of business because the Group has more limited historical information on which to base such estimates and judgments. A significant part of the Group’s current loss reserves is in respect of incurred but not reported (“IBNR”) reserves. This IBNR reserve is based almost entirely on estimates involving actuarial and statistical projections of the Group’s expectations of the ultimate settlement and administration costs. Accordingly, actual claims and claim expenses paid may deviate, perhaps substantially, from the reserve estimates reflected in the Group’s audited consolidated financial statements and unaudited interim consolidated financial statements, which could materially adversely affect the Group’s financial results.

If FIHL were deemed to be an investment company under the U.S. Investment Company Act of 1940 (the “Investment Company Act”), applicable restrictions could make it impractical for the Group to continue with its business as contemplated and could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

FIHL is not, and following this offering will not be, required to be registered as an “investment company” under the Investment Company Act, and FIHL intends to conduct its operations so that it will not be deemed to be an investment company under the Investment Company Act. The Investment Company Act and the rules and regulations thereunder contain detailed parameters for the organization and operation of investment companies. FIHL does not believe it is an investment company to which the Investment Company Act would apply because it is not and does not hold itself out as being primarily engaged, nor does it propose to engage primarily, in the business of investing, reinvesting, or trading in securities (the “primarily engaged test,” pursuant to Section

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3(a)(1)(A) of the Investment Company Act) and it does not own or propose to acquire “investment securities” (as defined in Section 3(a)(2) of the Investment Company Act) having a value exceeding 40% of the value of its total assets (exclusive of government securities and cash items) on an unconsolidated basis (the “40% Test,” pursuant to Section 3(a)(1)(C) of the Investment Company Act).

With respect to the 40% Test, FIHL directly owns all of the outstanding voting securities of FIBL and FUL, with FIBL owning 100% of Fidelis Europe Holdings Limited, which in turn owns 100% of FIID. More than 60% of the value of the total assets (exclusive of government securities and cash items) of FIHL, on an unconsolidated basis, consists of (a) voting securities of FIBL and FUL, and indirectly, via Fidelis Europe Holdings Limited, FIID, and (b) other assets that are not securities within the meaning of the Investment Company Act.

With respect to the primarily engaged test, for the twelve months ended December 31, 2022, the vast majority of the assets of each of FIBL, FUL and FIID were utilized in, or otherwise related to, the writing of insurance or the reinsurance of risks on insurance agreements, and represented either insurance reserves that FIHL has established or capital and surplus which is required to enable FIHL to conduct its business as a reinsurer.

If FIHL were to be deemed to be an investment company under the Investment Company Act, requirements imposed by the Investment Company Act, including limitations on FIHL’s capital structure, ability to transact business with affiliates and ability to compensate key employees, would make it impractical for the Group to continue its business as currently conducted, impair the agreements and arrangements between and among the Group and its clients, and materially and adversely affect the Group’s business, results of operations and financial condition.

Risks Relating to Recent Events

The full extent of the impacts of the ongoing Ukraine Conflict on the (re)insurance industry and on the Group’s business, financial condition and results of operations, including in relation to claims under the Group’s (re)insurance policies, are uncertain and remain unknown.

The U.S. and global markets are currently experiencing volatility and disruption following the ongoing Ukraine Conflict. In response to such invasion, the North Atlantic Treaty Organization (“NATO”) deployed additional military forces to eastern Europe. The United States, the United Kingdom, the European Union and other countries have announced various economic and trade sanctions, export controls and other restrictive actions against Russia, Belarus and related individuals and entities. These include, among other measures, the removal of certain financial institutions from the Society for Worldwide Interbank Financial Telecommunication (SWIFT) payment system, the imposition of comprehensive sanctions on certain persons and entities (including financial institutions) in Russia and Belarus and new export control restrictions targeting Russia and Belarus (including measures that restrict the movement of U.S.-regulated aircraft into or within Russia). The Ukraine Conflict and the resulting measures that have been taken, and could be taken in the future, by NATO, the United States, the United Kingdom, the European Union and other countries have created global security concerns that could have a lasting impact on regional and global economies. Although the severity and duration of the ongoing Ukraine Conflict is impossible to predict, the active conflict could lead to market disruptions, including significant and prolonged volatility in commodity prices, credit and capital markets, as well as supply chain interruptions. Additionally, Russian military actions and the resulting sanctions could adversely affect the global economy and financial markets and lead to instability and lack of liquidity in capital markets.

Further, in December 2022, the members of the G7, including the United States and United Kingdom, joined the E.U. in prohibiting regulated persons from providing a range of services, including issuing maritime insurance, related to the maritime transport of crude oil of Russian Federation origin, unless purchasers bought the oil at or below a price cap. The Group will consider providing insurance for future shipments of seaborne Russian crude oil, in compliance with these restrictions and all other applicable economic and trade sanctions.

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Although the Group will take measures designed to maintain compliance with applicable sanctions in connection with its activities, the Group cannot guarantee that it will be effective in preventing violations or allegations of violations. Violations, or allegations of violations, could result in civil and criminal penalties, including fines, for the Group or for responsible employees and managers, as well as negative publicity or reputational harm.

Due to the widespread impact of the ongoing Ukraine Conflict, which extends economically, geographically and financially, it is likely to directly or indirectly impact the markets in which the Group operates and some of the lines of business we write. It is possible that the war will create a domino effect, affecting the entirety of the Group’s business, including the ultimate premiums and costs of policies, through cost of materials and labor. The impact of some of or all these factors could cause significant disruption to the Group’s operations and materially impact its financial performance. The Group has already identified business lines which could suffer losses resulting from the ongoing sanctions. As aviation is a large component of the Group’s Specialty segment, any large losses in the aviation line of business could have a material and adverse impact on the performance of the Specialty segment generally. In light of the evolving nature of the Ukraine Conflict, there are a number of complexities and implications that will need to be evaluated and determined on an ongoing basis before the Group can reasonably estimate any potential losses. See “—Risks Relating to the Group’s Business and Industry—Industry-wide developments could adversely affect the Group’s business.”

Any of the above mentioned factors, or any other negative impact on the global economy, capital markets or other geopolitical conditions resulting from the Ukraine Conflict and subsequent sanctions, could have a material adverse effect on the Group’s business, financial condition and results of operations. The extent and duration of the Ukraine Conflict, resulting sanctions and any related market disruptions are impossible to predict, but could be substantial, particularly if current or new sanctions continue for an extended period of time or if geopolitical tensions result in expanded military operations on a global scale. Most of the significant factors arising out of the ongoing Ukraine Conflict are beyond the Group’s control and any such disruptions may also have the effect of heightening many of the other risks described in this “Risk Factors” section. If these disruptions or other matters of global concern continue for an extended period of time, the Group’s business, financial condition and results of operations may be materially adversely affected.

We may be subject to litigation which could adversely affect our business.

The Group, in common with the insurance industry in general, is subject to litigation, mediation and arbitration, and regulatory and other sectoral inquiries in the normal course of its business in a number of foreign jurisdictions. For example, as a result of the insurers having denied claims of the aircraft lessors in respect of the unreturned aircraft currently located in Russia as a result of the Ukraine Conflict, aircraft lessors have instituted proceedings in the U.K., the U.S. and Ireland against upwards of 60 (re)insurers, including certain Group entities. Fidelis has been named in multiple proceedings. For additional information, see “Management’s Discussion and Analysis of Operations—Recent Developments and Activity.”

While management believes that these claims will not have a material adverse effect on the Group’s financial position, given the large or indeterminate amounts sought in certain of these actions, and the inherent unpredictability of litigation, it is possible that an adverse outcome impacting several of the outstanding claims could, from time to time, have a material adverse effect on the Group’s results of operations or cash flows.

Our business, financial condition and results of operations may be adversely affected by an epidemic, pandemic or any other public health crisis and we may face risks related to Severe Acute Respiratory Syndrome (SARS), H1N1 influenza, H5N1 influenza, H7N9 influenza, H3N2 influenza and COVID-19 which could significantly disrupt our operations resulting in material adverse impacts to our business, financial condition and results of operations.

The widespread outbreak of an illness or any other communicable diseases, or any public health crisis that results in economic or trade disruptions could negatively impact our business and the businesses of our policyholders.

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Our results of operations may be affected by the impact on the global economy and businesses that COVID-19 (or another pandemic or epidemic) has had to date or may have in the future. Global financial markets have suffered downturns and volatility as a result of the COVID-19 pandemic, which may, as a result of the resurgence of existing or the emergence of new COVID-19 strains (or similar pandemics or epidemics), continue to have a sustained impact on businesses across the world. Risks relating to COVID-19 and future pandemics or epidemics may become more expensive or impossible to insure against. If any of the global impacts of COVID-19 (or another pandemic or epidemic) resurge for a sustained period of time or should any of the risks identified above materialize leading to an economic downturn and heightened volatility, it could have a material adverse effect on our business, financial condition and results of operations.

It is possible that a resurgence of COVID-19 (or another pandemic or epidemic) will cause an economic slowdown, and it is possible that it could cause a global recession. There is a significant degree of uncertainty and lack of visibility as to the extent and duration of any such slowdown or recession. Given the significant economic uncertainty and volatility created by COVID-19 (or another pandemic or epidemic), it is difficult to predict the nature and extent of impacts on our business.

For example, economic uncertainty continued throughout 2022 due not only to the COVID-19 pandemic, but also the Ukraine Conflict, energy price rises and cost of living increases. Global economies have recorded low levels of growth as they emerge from the COVID-19 pandemic and the low levels of growth have been further affected by increased geopolitical uncertainty due to the Ukraine Conflict. These events, if worsened, may have a significant impact on the performance on our business, financial condition and results of operations.

Recent events have adversely impacted, and may continue to adversely impact, the value of the Group’s investment portfolio and may affect the Group’s ability to access liquidity and capital markets financing or receive dividends from its operating subsidiaries.

Recent events, including the outbreak of the ongoing Ukraine Conflict, have introduced financial market volatility that has adversely impacted, and may continue to adversely impact, the value of the Group’s investment portfolio and, if these global conditions persist, ongoing market volatility could affect the Group’s ability to access liquidity and other capital markets financings. Inflation, rising interest rates, reduced liquidity in financial markets and a continued slowdown in global economic conditions have increased the risk of defaults and downgrades and have increased the volatility in the value of many of the investments the Group holds. In addition, the steps taken by governmental institutions in response to recent events (including the imposition of sanctions on Russia following its invasion of Ukraine), and the costs of such actions, may eventually lead to higher-than-expected inflation and further financial stress on global financial markets, including government bond markets.

The recent market volatility also caused significant increases in credit spreads which, if continuing, may negatively impact the Group’s ability to access liquidity and capital markets financing such that it may not be available or may only be available on unfavorable terms. Regulators in certain jurisdictions imposed dividend restrictions on insurance companies, which impact liquidity for holding companies that have insurance subsidiaries in those jurisdictions. For example, the European Insurance and Operational Pensions Authority (“EIOPA”), the E.U.’s insurance regulator, has recommended that any dividend distributions should not exceed thresholds of prudency given the continuing uncertainty over the impact of the pandemic. As a holding company with no direct operations, FIHL relies on dividends and other permitted payments from its subsidiaries and it may be unable to make distributions on its preference securities or principal and interest payments on its debt and to pay dividends to holders of Common Shares if its operating subsidiaries are unable to pay dividends to it. See “—Risks Relating to Financial Markets and Liquidity.”

The current inflationary environment could have a material adverse impact on the Group’s operations.

Steps taken by governments throughout the world in response to the recent economic and geopolitical climate, expansionary monetary policies and other factors have led to an inflationary environment. In operating

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our business, we are experiencing the effects of inflation, including increased labor and construction costs. Furthermore, the Group’s operations, like those of other insurers and reinsurers, are susceptible to the effects of inflation because premiums are established before the ultimate amounts of losses and loss adjustment expenses are known. Although the Group considers the potential effects of inflation when setting premium rates, premiums may not fully offset the effects of inflation and thereby essentially result in underpricing the risks insured and reinsured by the Group. Loss reserves include assumptions about future payments for settlement of claims and claims-handling expenses, such as the value of replacing property, associated labor costs for the property business the Group writes, and litigation costs. To the extent inflation causes costs to increase above loss reserves established for claims, the Group will be required to increase loss reserves with a corresponding reduction in net income in the period in which the deficiency is identified, which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. Unanticipated higher inflation could also lead to higher interest rates, which would negatively impact the value of the Group’s fixed maturity securities and potentially other investments.

Risks Relating to the Group’s Strategic Relationship with Fidelis MGU

The Group relies on Fidelis MGU for services critical to its underwriting and other operations. The termination of or failure by Fidelis MGU to perform under one or more agreements governing the Group’s outsourced relationship with Fidelis MGU may cause material disruption in our business or materially adversely affect our financial results.

On July 23, 2022, FIHL and Fidelis MGU entered into a Cooperation Agreement agreeing to cooperate regarding certain matters relating to this offering and the Separation Transactions. FIHL and Fidelis MGU have also entered into a number of agreements governing the outsourced relationship, including the Framework Agreement, a series of Delegated Underwriting Authority Agreements (as defined below, see “Material Contracts and Related Party Transactions—Framework Agreement”) and the Inter-Group Services Agreement (see “Material Contracts and Related Party Transactions—Framework Agreement”).

The Framework Agreement, under which the Group secures business from Fidelis MGU, has a rolling initial term of 10 years. Years one to three will roll automatically (each year resetting for a new 10-year period) and the notice to roll will be deemed given at the end of years one, two and three (i.e., the years roll automatically and will not be subject to any underwriting target or other preconditions to rolling). From year four onwards, the Framework Agreement will roll at the written election of FIHL, with such election to be delivered at least 90 days prior to the commencement of the subsequent contract year. Any decision by FIHL to elect not to roll the Framework Agreement on or after year four will mean that the remainder of the 10-year term then in effect will continue in place (i.e., the Framework Agreement will have a further nine years to run in the first year following the election by FIHL not to roll the Framework Agreement). Additionally, each party has certain rights to terminate the Framework Agreement early. See “Material Contracts and Related Party Transactions—Framework Agreement.”

Under the terms of the relevant agreements, Fidelis MGU will also provide detailed reporting to the Group on a monthly or quarterly basis, depending on the nature of the report. Such reports will include, among other things, (i) accounting information (i.e., premiums written and earned, fees and loss reserves); (ii) underwriting information (including all insurance business underwritten under the Delegated Underwriting Authority Agreements); and (iii) claims handling information. If Fidelis MGU fails to perform any of its reporting obligations, the Group could be severely impacted, including by FIHL being unable to comply with its own reporting obligations as a listed company.

Due to the Group’s dependency on Fidelis MGU and the Group’s conduct of business being subject to the parameters and limitations set forth in the Framework Agreement, if the Framework Agreement or any of the Group’s agreements with Fidelis MGU are terminated or Fidelis MGU fails to perform any of the services outsourced to it under the Framework Agreement or the other related agreements noted above, the Group may be required to hire staff to provide such services itself or retain a third party to provide such services, and no

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assurances can be made that the Group would be able to do so in a timely, efficient or cost-effective manner. The Group could therefore suffer, among other things, non-renewals and loss of business, financial loss, disruption of business, liability to third parties, regulatory intervention and reputational damage, any of which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Pursuant to the agreements between the Group and Fidelis MGU, the Group retains an oversight and supervisory role over Fidelis MGU’s active role in executing the Group Annual Plan and each of the Subsidiary Annual Plans. If the Group’s monitoring efforts prove inadequate, this could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Pursuant to the Framework Agreement, the Delegated Underwriting Authority Agreements and the Inter-Group Services Agreement, certain key underwriting and non-underwriting functions of the Group have been outsourced to Fidelis MGU and Fidelis MGU’s employees are authorized to conduct business in accordance with the Group Annual Plan and each of the Subsidiary Annual Plans, as overseen by the Group, whose role is primarily supervisory in nature. The Group relies on established parameters. Although the Group monitors such business on an ongoing basis, its monitoring efforts may not be adequate to prevent Fidelis MGU or the designated employees from exceeding their authority, committing fraud or otherwise failing to comply with the terms of the agreements governing its relationship with the Group, including the Framework Agreement and the Delegated Underwriting Authority Agreements. Over time, such oversight may become cumbersome and lack of familiarity between the two separate groups could lead to operational missteps. To the extent Fidelis MGU exceeds its authority, commits fraud or otherwise fails to comply with the terms of agreements governing its relationship with the Group, the Group’s financial condition and results of operations could be materially adversely affected.

Some executive officers and key personnel of Fidelis MGU are critical to the Group’s business; Fidelis MGU’s failure to retain such key personnel could seriously affect the Group’s ability to conduct its business and execute the Group Annual Plan.

The Group’s future success depends to a significant extent on the efforts of Richard Brindle and other senior management and key personnel employed by Fidelis MGU and FIHL to implement its business strategy. The majority of senior employees of Previous Fidelis, including Richard Brindle, are now employed by Fidelis MGU. There can be no assurance, however, that such key personnel will remain employed by Fidelis MGU. There are only a limited number of available and qualified executives with substantial experience in the (re)insurance industry and the procurement of new employees could be hindered by factors outside of the Group’s control. Accordingly, Fidelis MGU’s or FIHL’s loss of the services of one or more of the members of the senior management team or other key personnel, including Richard Brindle, could significantly and negatively affect its ability to execute the Group Annual Plan, which could, in turn, have a material adverse effect on the Group’s business.

Although each of Fidelis MGU and FIHL has executed employment agreements with respective key personnel, such executives and other senior management are free to resign from their roles, in accordance with the notice and non-compete provisions as set out in their respective employment agreements. Further, Fidelis MGU and FIHL do not currently maintain key man life insurance with respect to any of their respective management. If any member of management or other key employee dies or becomes incapacitated, or leaves Fidelis MGU or FIHL to pursue employment opportunities elsewhere, they would be responsible for locating an adequate replacement for such individual and for bearing any related cost. To the extent that either Fidelis MGU or FIHL is unable to locate an adequate replacement or is unable to do so within a reasonable period of time, the Group’s business may be significantly and negatively affected.

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The Group’s historical track record, including the track record of some of the executives of Fidelis MGU, may not be indicative of our future growth.

The Group has experienced rapid growth since its inception, with GPW of $3.0 billion for the year ended December 31, 2022 and GPW increasing to $1.2 billion in the three months ended March 31, 2023 compared to $1.0 billion for the three months ended March 31, 2022, and the Group expects to continue to have access to more opportunities following completion of the Separation Transactions through its partnership with Fidelis MGU. There can be no assurance that the Group’s business, or the ability of Fidelis MGU to source underwriting opportunities for the Group, will continue to grow and expand at the same rate since inception, if at all. Various executives that will be executives of Fidelis MGU, including Mr. Brindle, have had success throughout their careers. There is no assurance that the executives’ track records, including Mr. Brindle’s track records at Lloyd’s and Lancashire, will continue after the Separation Transactions. If the Group is unable to increase the amount of premium that is written successfully, or if Fidelis MGU cannot source sufficient opportunities for the Group, this may have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Any disagreements between the Group and Fidelis MGU could lead to a deterioration of the commercial relationship between the parties, which could result in the Framework Agreement, the Inter-Group Services Agreement or the Delegated Underwriting Authority Agreements being terminated.

Any disagreements between the Group and Fidelis MGU in respect of the Framework Agreement, the Inter-Group Services Agreement, the Delegated Underwriting Authority Agreements, the Group Annual Plan or the Subsidiary Annual Plans could lead to a deterioration of the commercial relationship between the parties.

For example, the base case assumption with respect to the Subsidiary Annual Plans agreed between the Group and Fidelis MGU is that each Subsidiary Annual Plan will be renewed on the basis of premiums written in the prior year, subject to any changes to such Subsidiary Annual Plans agreed between the Group and Fidelis MGU, as permitted. The Group and Fidelis MGU will have the opportunity to agree to certain changes to the Subsidiary Annual Plans during the annual negotiation or through the Mid-Year Change Procedure (as defined herein). The Framework Agreement contains certain provisions aimed at resolving disputes in relation to any proposed changes to the Subsidiary Annual Plans that may arise between the parties. For example, in respect of the annual negotiation, should a particular change to the relevant Subsidiary Annual Plan be requested by a party and denied three years in a row, it will be referred to the non-calculation dispute resolution procedure to be resolved. Such non-calculation dispute resolution procedure may also be used if the parties are unable to agree on the specific parameters of the proposed changes, while being agreeable to such changes in principle. See “Material Contracts and Related Party Transactions—Framework Agreement—Subsidiary Annual Plans.”

To the extent any suggested change to any of the Subsidiary Annual Plan is not agreed to or is strongly contested by either party, this could lead to a deterioration of the commercial relationship between the parties, which could ultimately result in FIHL choosing not to roll the term of the Framework Agreement leading to a termination. If the Framework Agreement is terminated, the Inter-Group Services Agreement or the Delegated Underwriting Authority Agreements which govern the Group’s outsourcing arrangements may also terminate altogether or the Group’s business model may change materially (if, for example, the Group is forced to find an alternative services provider to carry on its outsourcing strategy). Either of those outcomes could have a material adverse effect on the Group’s financial condition and results of operations.

There can be no guarantee that the terms of the Separation Transactions, the Framework Agreement, the Delegated Underwriting Authority Agreements and the other outsourcing agreements and arrangements between the Group and Fidelis MGU are as favorable to the Group as if they had been negotiated with an unaffiliated third party.

There can be no guarantee that the terms of the Separation Transactions, the Framework Agreement and the other outsourcing agreements and arrangements between the Group and Fidelis MGU, including the fees payable to Fidelis MGU, are as favorable to the Group as if they had been negotiated with an unaffiliated third party. In addition, the Group’s ongoing relationship with Fidelis MGU may impact how the Group enforces its rights under the agreements.

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MGU HoldCo owns 9.9% of our Common Shares. Additionally, a number of FIHL’s current shareholders are also shareholders in MGU TopCo and, in some cases, employees of Fidelis MGU. As such, conflicts of interest may arise, which could result in decisions being taken that are not in the best interest of the Group’s shareholders as a whole.

Conflicts of interest may exist or could arise in the future with Fidelis MGU due to a number of FIHL’s current shareholders being employed by Fidelis MGU or holding shares in MGU TopCo. Conflicts may arise with respect to, without limitation: (i) the enforcement of agreements between the Group and Fidelis MGU, (ii) making changes to the Group Annual Plan and each of the Subsidiary Annual Plans, (iii) the management of Fidelis MGU by persons who are shareholders of FIHL, (iv) shareholders who hold shares in both FIHL and MGU TopCo, and (v) conflicts arising from the exercise of the ROFO and ROFR rights (each as defined below, see “Material Contracts and Related Party Transactions—Framework Agreement—Exclusivity, Rights of First Offer and Rights of First Refusal”) of the Group and Fidelis MGU. MGU HoldCo owns 9.9% of FIHL’s outstanding Common Shares. The foregoing conflicts and the interests of the Group on one hand and Fidelis MGU on the other could result in decisions being taken that are not in the best interest of the Group’s shareholders as a whole.

The failure of Fidelis MGU to effectively manage the Group’s claims could adversely affect the Group’s business, prospects, financial condition or results of operations.

Under the terms of the Framework Agreement and the Delegated Underwriting Authority Agreements, the claims management activities will be managed by Fidelis MGU, with the Group retaining an oversight function. See “Business—Claims.” The Group therefore relies on Fidelis MGU to facilitate, oversee and efficiently manage the claims process for the Group’s policyholders in line with the parameters set forth in the Framework Agreement and the respective Delegated Underwriting Authority Agreements. To the extent Fidelis MGU exceeds its authority or otherwise fails to comply with the terms of the Framework Agreement and the Delegated Underwriting Authority Agreements and such non-compliance leads to inappropriate or negligent claims management, the Group’s business, prospects, financial condition and results of operations may be materially adversely affected. Beyond intentional breaches there are also a number of other factors beyond Fidelis MGU’s control that could affect the ability of Fidelis MGU to effectively manage claims of our policyholders.

Any failure by Fidelis MGU to effectively manage the claims process, including failure to pay claims accurately, could lead to material litigation, undermine the Group’s reputation in the marketplace or impair the Group’s corporate image and adversely affect our ability to renew existing policies or write new policies. Any of the aforementioned factors, or any other negative impact of Fidelis MGU’s claims management process could have a material and adverse impact on the Group’s business, prospects, financial condition and results of operations.

Risks Relating to the Operations Supporting the Group’s Business

The Group depends, in certain cases, on its policyholders’ evaluations or disclosures of the exposures associated with their insurance underwriting, which may subject the Group to reinsurance disputes, liability, regulatory actions or reputational damage.

The Group does not separately evaluate each of the original individual exposures assumed under some of its reinsurance business (such as quota share contracts in which the Group expects to assume an agreed-upon percentage of each underlying insurance contract being reinsured or excess of loss contracts), including on policyholders bound by another person to whom underwriting authority has been delegated by the Group (such as third-party MGUs) on a “non-prior submit” basis. In these situations, the Group is largely dependent on the original underwriting decisions made by ceding companies. The Group is subject to the risk that its policyholders may not have adequately evaluated or disclosed the insured exposures and that the premiums ceded may not adequately compensate the Group for the exposures it will assume. The Group may not evaluate separately each of the individual claims that may be made on the underlying insurance contracts under reinsurance contracts. Therefore, the Group may be dependent on the original claims decisions made by its policyholders. To the extent that a

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customer fails to evaluate adequately the insured exposures or the individual claims made thereunder, the Group’s business, prospects, financial condition or results of operations could be significantly and negatively affected.

Certain elements of the Group’s business may also be written on the basis of sub-delegated authority (in other words, Fidelis MGU may further delegate underwriting authority to a third-party managing general underwriters or other intermediary), as allowed for in the Framework Agreement and the Delegated Underwriting Authority Agreements. The Group will establish the parameters under which Fidelis MGU can sub-delegate authority and Fidelis MGU will operate and maintain procedures to manage its sub-delegated authority relationships, but nonetheless there are risks associated with such relationships, including but not limited to, fraud by employees or representatives of persons to whom Fidelis MGU sub-delegates authority, information technology failures, failure to comply with referral and escalation procedures, inaccurate or incomplete bordereau reporting, and credit risk. Furthermore, Fidelis MGU and in turn, the Group, relies on the underwriting judgment of such sub-delegated agents and intermediaries, which may be different from the decisions that would be made by the employees of Fidelis MGU acting within the parameters set forth in each Subsidiary Annual Plan or the Delegated Underwriting Authority Agreements.

Operational risk exposures, such as human or systems failures (including outsourcing arrangements), are inherent in the Group’s business and may result in losses.

Operational exposures and losses can result from, among other things, errors, failure to document transactions properly or to obtain proper internal authorization, failure to comply with regulatory requirements, information technology failures, bad faith delayed claims payment, fraud and external events, such as political unrest, state emergency or industrial actions which could result in operational outage. The Group relies on Fidelis MGU and other third parties for information technology and application systems and infrastructure, which are exposed to certain limitations and risk of systemic failures. Any such outage could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. In addition, given the Group’s outsourced relationship with Fidelis MGU, which could also include writing business on a sub-delegated authority basis with a third-party managing general underwriter or other intermediary, Fidelis MGU or such other sub-delegate could bind the Group on business outside of a designated authority resulting in significant losses.

The Group also relies heavily on third parties, including Fidelis MGU, for information technology and application systems and infrastructure. The Group believes that such information technology and application systems and infrastructure are critical to the Group’s business. Such information technology and application systems and infrastructure are an important part of the Group’s underwriting process and its ability to compete successfully. The Group also licenses certain of its key systems and data from third parties, including Fidelis MGU, and cannot be certain that it will have continuous access to such third-party systems and data, or those of comparable service providers, or that the Group’s information technology or application systems and infrastructure will operate as intended. The third-party modeling software that the Group uses is important to the Group and any substantial or repeated failures in the accuracy or reliability of such software or the human interpretation of its outputs could result in a deviation from the Group’s expected underwriting results. Further, the third parties’ programs and systems may be subject to defects, failures, material updates or interruptions, including those caused by worms, viruses or power failures.

Failures in any of these systems could result in mistakes made in the confirmation or settlement of transactions, or in transactions not being properly booked, evaluated, priced or accounted for or delays in the payment of claims. Any such eventuality could cause the Group to suffer, among other things, financial loss, disruption of business, liability to third parties, regulatory intervention and reputational damage, any of which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

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Technology breaches or failures, including those resulting from a malicious cyber-attack on the Group or its business partners or service providers, could disrupt or otherwise negatively impact the business.

The Group relies on information technology systems and infrastructure to process, transmit, store and protect the electronic information, financial data and proprietary models that are critical to the Group’s business. Furthermore, a significant portion of the communications between the Group’s employees and the Group’s business, banking and investment partners depends on information technology and electronic information exchange. Like all companies, the Group’s information technology systems are vulnerable to data breaches, interruptions or failures due to events that may be beyond the control of the Group, including, but not limited to, natural disasters, theft, terrorist attacks, computer viruses, hackers and general technology failures. Despite safeguards, disruptions to and breaches of the Group’s information technology systems have occurred in the past and may occur in the future, which may negatively impact (possibly to a material extent) the Group’s business. See “—Risks Relating to Regulation of the Group—Data protection failures could disrupt the Group’s business, damage its reputation and cause losses.”

The inability to attract, retain and manage key employees could restrict the Group’s ability to implement its business strategy.

The Group’s future success depends to a significant extent upon the Group’s ability to continue to attract and retain key employees to implement the Group’s long-term business strategy. Some new members of the Group’s management team may not have worked together prior to their employment with the Group, and the management team may not operate together as efficiently as an otherwise similar management team that has been operating together for a significant amount of time. Within the Group’s industry it is common for employers to seek to restrict an employee’s ability to work for a competitor or to engage in business activities with the customers or staff of a former employer after leaving employment. The extent of any such post-termination restrictions and the extent to which any alleged contractual restrictions are enforceable is highly fact-specific and dependent upon local laws in the applicable jurisdiction.

The Group may also suffer from future events that require governments to introduce similar measures to those imposed during the COVID-19 pandemic, such as social distancing measures, travel restrictions and border closures between the countries in which the Group operates. If such measures are reintroduced, the Group’s key employees may be unable to travel freely, or participate in and carry out some of their usual responsibilities. In addition, we operate in a highly competitive labor market which experiences labor shortages and a high rate of employee turnover, which requires us to increase salary and wage rates, bonuses and other incentives in order to attract and retain talented employees. The Group’s inability to hire, retain or fully utilize talented and experienced personnel, whether resulting from the foregoing reasons or otherwise, could delay or prevent the Group from fully implementing its business strategy and would significantly and negatively affect its business.

The Group’s ability to implement its business strategy could be adversely affected by Bermuda employment restrictions.

Under Bermuda law, non-Bermudians (other than spouses of Bermudians and holders of Permanent Residents’ Certificates) may not engage in any gainful occupation in Bermuda without a valid government work permit. Except for our Chief Executive Officer and other “chief” officer positions (where the advertising requirement (see below) is automatically waived) or where otherwise specifically waived, a work permit may be granted or renewed upon showing that, after proper public advertisement, no Bermudian, spouse of a Bermudian, or holder of a Permanent Resident’s Certificate who meets the minimum standards reasonably required by the employer has applied for the job. A work permit is issued with an expiry date (up to five years) and no assurances can be given that any work permit will be issued or, if issued, renewed upon the expiration of the relevant term. If work permits are not obtained, or are not renewed, for the Group or Fidelis MGU principal employees who are located in Bermuda, the Group would lose its services, which could significantly and negatively affect its business and could also delay or prevent the Group from fully implementing its business

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strategy. The Group monitors any actual or potential legislative changes regarding the Bermuda Government’s immigration policies and any effects this may have on the Group’s employment practice, policies and procedures.

The failure to retain a letter of credit facility and/or the need to provide assets directly as collateral may significantly and negatively affect the Group’s ability to successfully implement its business strategy.

Certain of the Group’s reinsurance customers may require the relevant Group company to post a letter of credit (“LOC”) and/or provide assets directly as collateral, while collateral may also be required from time to time for regulatory purposes. The Group currently maintains various LOC facilities, with Lloyds Bank plc, Barclays Bank plc, Bank of Montreal and Citibank N.A., London Branch.

An event of default under any of the LOC facilities (including as a result of events that are beyond the Group’s control) may require the Group to liquidate assets held in these facilities, have an adverse effect on the Group’s liquidity position as the facility providers have a security interest in the collateral posted, or require the Group to take other material actions. Any such forced sale of these investment assets could negatively affect the return on the Group’s investment portfolio, which could negatively affect the types and amount of business the Group chooses to underwrite. A default under any of the LOC facilities may cause the facility providers to exercise control over the collateral posted, negatively affecting the Group’s ability to earn investment income or to pay claims or other operating expenses. Additionally, a default under any of these facilities may have a negative impact on the Group’s relationships with regulators, rating agencies and banking counterparties.

In addition, if the amount of assets the Group has to post as collateral to support cedant demand or regulatory requirements increases beyond a threshold, the Group may be left with insufficient liquid, available assets to support the Group Annual Plan and each of the Subsidiary Annual Plans and/or day-to-day operations. Such risk is increased in relation to FIBL and FUL which, in the event of losing their certified U.S. reinsurer status pursuant to certain excess and surplus licenses, would be required to post a much higher amount of collateral to carry on their business. This consequently could impact the Group’s business, prospects, financial condition or results of operations. Further, the inability to renew or maintain the LOC facilities may significantly limit the amount of reinsurance the Group can write, or require the Group to modify its investment strategy. The Group may need additional LOC capacity as it grows, and if the Group is unable to renew, maintain or increase its LOC facilities or is unable to do so on commercially acceptable terms, such a development could significantly and negatively affect the Group’s ability to implement its business strategy. In particular, the Group anticipates arranging for additional LOC capacity for its subsidiaries in connection with obligations to post collateral in connection with certain reinsurance transactions. Furthermore, the Group expects to seek renewals of its existing LOC facilities. If the Group is unable to obtain and retain LOC facilities on commercially acceptable terms, this could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Risks Relating to the Group’s Reliance on Third Parties in the Operation of its Business

The Group is reliant on third-party service providers and their IT systems, and their failure could lead to an interruption in the Group’s business activities, which could have a material adverse effect on the Group’s business.

The Group is reliant on third parties, such as Fidelis MGU, for the provision of important services it needs to run its business, including, without limitation, finance, actuarial and underwriting systems and processes and IT infrastructure and systems including software. Any of these service providers failing to perform at the necessary level may have a significant and adverse impact on the business of the Group and its IT systems.

The Group requires complex and extensive IT systems, which are being updated continuously, to run its business. During any projects to develop the Group’s IT systems, it is particularly susceptible to outages or weakness related to such systems. Any failure of these systems or by the Group’s service providers could lead to an interruption in the Group’s business activities which, in turn, could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

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The expanding volume and sophistication of computer viruses, hackers and other external hazards such as the use of malware or other malicious code or attack, catastrophic events system failures and disruptions, as well as employee or third-party errors or malfeasance, may also increase the vulnerability of the Group’s IT and data systems to security breaches. The Group has previously suffered cyber-attacks on its IT infrastructure and the Group believes it has taken the necessary steps to mitigate any future attacks. The Group has also increased the amount of internal training and is employing stringent IT infrastructure reviews. However, there can be no assurance that these steps will in fact prevent future attacks. These increased risks expose the Group to potential data loss and damages and potentially significant increases in compliance and litigation costs, and such exposure could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The Group depends on brokers and other intermediaries to distribute its products, and the loss of business provided by brokers and other intermediaries could adversely affect it.

The distribution model for the Group’s products is built on long-term relationships with quality clients and respect for the core broker distribution model which is fully outsourced to Fidelis MGU. The Group is therefore indirectly dependent upon brokers and other intermediaries to distribute its products. Brokers and certain other intermediaries are independent and therefore no broker or such other intermediary is committed to recommend or sell the products of the Group. Accordingly, Fidelis MGU’s relationships with brokers and other intermediaries distributing its products will be important. A broker assesses which insurance companies are suitable for it and its customers by considering, among other things, the security of claims payment and service, and prospects for future investment returns in the light of a company’s product offering, personnel, past investment performance, financial strength and perceived stability, ratings and the quality of the service provided to the broker and its customer. Larger insurers and reinsurers may have more commercial influence with certain insurance and reinsurance brokers, either generally or in certain underwriting lines. A broker then determines which products are most suitable by considering, among other things, product features and price. An unsatisfactory assessment of the Group and its products based on any of these factors could result in the Group generally, or in particular certain of its products, not being actively marketed by brokers to their customers. Failure to maintain a positive relationship with its brokers and competitive distribution network could result in a loss of market share or a reduction of the Group’s premium volumes or an increase in policy lapses and withdrawals, which could result in reduced fee and premium income, and, in turn, have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

The involvement of insurance and reinsurance brokers and other intermediaries subjects the Group to their credit risk.

Pursuant to its outsourced relationship with Fidelis MGU, the Group will generally pay all of the amounts owed on claims under its insurance and reinsurance contracts first to Fidelis MGU, who will then pass on the payment to the various brokers or other intermediaries, and these brokers or other intermediaries (as applicable) will, in turn, pay these amounts over to the clients that have purchased insurance or reinsurance from the Group. If Fidelis MGU, a broker or other intermediary fails to make its relevant payment, it is possible that the Group will be liable to the client for the deficiency because of local laws or contractual obligations. Likewise, in certain jurisdictions, when the insured or ceding insurer pays premiums for these policies to brokers or other intermediaries for payment over to the Group, these premiums might be considered to have been paid and the insured or ceding insurer will no longer be liable to the Group for those amounts, whether or not the Group actually receives the premiums “up the chain” from Fidelis MGU, a broker or other intermediary. Consequently, both the Group and Fidelis MGU assume a high degree of credit risk associated with brokers and other intermediaries, including in relation to any sub-delegation, around the world with respect to most of its insurance and reinsurance business, its inwards premium receivable from insureds and cedants, and on any amounts recoverable in relation to subrogation and salvage and from reinsurers.

Furthermore, the concentration of the Group’s business in a small number of key brokers may subject it to reduced premium income. During the year ended December 31, 2022, GPW generated from or placed by Aon plc, Marsh & McLennan Companies and Guy Carpenter & Company LLC (which is also an affiliate of Marsh &

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McLennan Companies) collectively accounted for 35% of the Group’s consolidated GPW, with Aon plc accounting for 15% and Marsh & McLennan Companies, Inc. (and certain of its affiliates) accounting for 20% of our consolidated GPW during 2022. Other key brokers, each of whom has accounted for less than 10% of the GPW generated during the years ended December 31, 2018 to December 31, 2022, include, among others, Willis Towers Watson and TigerRisk Partners, LLC. For more information, see note 13(c) (“Commitments and Contingencies—Concentration of credit risk”) to the Group’s unaudited consolidated financial statements included elsewhere in this prospectus and note 17(d) (“Commitments and Contingencies—Concentration of credit risk”) to the Group’s audited consolidated financial statements included elsewhere in this prospectus. Loss of all or a substantial portion of the business provided by one or more of the Group’s key (re)insurance brokers could result in reduced premium income, which, in turn, could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Risks Relating to Financial Markets and Liquidity

The Group’s business, prospects, financial condition or results of operations may be adversely affected by reductions in the aggregate value of the Group’s investment portfolio.

The Group’s operating results depend in part on the performance of the Group’s investment portfolio. The Group’s funds are invested by professional investment management firms in accordance with the Group’s investment guidelines. The Group’s investments are subject to a variety of financial and capital market risks including, but not limited to, changes in interest rates, credit spreads, equity and commodity prices, foreign currency exchange rates, increasing market volatility and risks inherent to particular securities. Prolonged and severe disruptions in the public debt and equity markets, including, among other things, volatility of interest rates, widening of credit spreads, bankruptcies, defaults, significant ratings downgrades, geopolitical instability, and a decline in equity or commodity markets, may cause significant losses in the Group’s investment portfolio. Market volatility can make it difficult to value certain securities if their trading becomes infrequent. Depending on market conditions, the Group could incur substantial additional realized and unrealized investment losses in future periods. This could have a material effect on certain of the Group’s investments. The investment guidelines currently implemented by the Group focus on investment primarily in fixed maturity and cash products and allow a small portion of the Group’s portfolio to be allocated to alternative or other investments. Depending on current and future events and market conditions and their impact on the Group’s investments, the investment guidelines are subject to change.

For instance, the Group’s investment portfolio (and, specifically, the valuations of investment assets it holds) has been, and may continue to be, adversely affected as a result of market valuations impacted by the COVID-19 pandemic and any other public health crisis, the Ukraine Conflict and other global economic and geopolitical uncertainty regarding their outcomes. These include changes in interest rates, declining credit quality of particular investments, reduced liquidity, fluctuating commodity prices, international sanctions, and related financial market impacts from the sudden, continued slowdown in global economic conditions generally. Further, extreme market volatility, such as the markets are experiencing now as a result of the ongoing Ukraine Conflict, may leave the Group unable to react to market events in a prudent manner consistent with the Group’s historical practices in dealing with more orderly markets.

Separately, the occurrence of large claims may force the Group to liquidate securities at an inopportune time, which may cause the Group to realize capital losses. Large investment losses could decrease the Group’s asset base and thereby affect the Group’s ability to underwrite new business. Additionally, such losses could have a material adverse impact on the Group’s shareholders’ equity, business and financial strength and debt ratings.

The aggregate performance of the Group’s investment portfolio also depends to a significant extent on the ability of the Group’s investment managers to select and manage appropriate investments. As a result, the Group is also exposed to operational risks which may include, but are not limited to, a failure of the Group’s investment managers to perform their services in a manner consistent with the Group’s investment guidelines, technological and staffing deficiencies, inadequate disaster recovery plans, interruptions to business operations due to impaired

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performance or failure or inaccessibility of information or IT systems. The result of any of these operational risks could adversely affect the Group’s investment portfolio, financial performance and ability to conduct the Group’s business.

The Group’s results of operations and investment portfolio may be materially affected by conditions impacting the level of interest rates in the global capital markets and major economies, such as central bank policies on interest rates and the rate of inflation.

As a global insurance and reinsurance company, the Group is affected by the monetary policies of the U.S. Federal Reserve Board, The Bank of England, the European Central Bank and other central banks around the world. Following the financial crisis of 2007 and 2008, and again most recently as a result of the COVID-19 pandemic, these central banks have taken a number of actions to spur economic activity such as keeping interest rates low and enacting quantitative easing. Unconventional monetary policy from the major central banks, the reversal of such policies, a shift to monetary tightening policies and moderate global economic growth remain key uncertainties for markets and the Group’s business.

For example, in one of the Group’s key markets for its products, the U.S. debt ceiling and budget deficit concerns continue to present the possibility of credit-rating actions, economic slowdowns, or a recession for the U.S. The impact of any negative action regarding the U.S. government’s sovereign credit rating could adversely affect the U.S. and global financial markets and economic conditions. In addition, policies that may be pursued by the Biden administration and the legislation that may be introduced by the U.S. Congress and Senate, could result in market volatility in the short term. These developments could cause more volatility in interest rates and borrowing costs, which may negatively impact the Group’s ability to access the debt markets on favorable terms. Continued adverse economic conditions could have a material adverse effect on the Group’s business, financial condition and results of operations. These and any future developments and reactions of the credit markets toward these developments could cause interest rates and borrowing costs to rise, which may negatively impact the Group’s ability to obtain debt financing on favorable terms.

Although the Federal Reserve previously cut interest rates in 2019 and 2020 to stimulate the U.S. economy and address the COVID-19 pandemic, and interest rates remained relatively low throughout 2020 and most of 2021, the Federal Reserve may change its monetary policy at any time. The U.S. economy commenced showings signs of potential recovery due to the fiscal package and government stimulus plans introduced by the Biden administration as well as the Federal Reserve’s continued engagement in quantitative easing. The Federal Reserve has been steadily increasing the target interest rates throughout 2022 in an effort to help curb inflation, a trend that has continued into 2023 with a further increase to 5.00%-5.25% in May 2023. If the Federal Reserve further raises target interest rates, or if interest rates otherwise rise, the Group may be exposed to unrealized losses on its fixed maturity securities. Similarly, The Bank of England’s Monetary Policy Committee has steadily been increasing rates throughout 2022 and into 2023 with the most recent interest rate increase of 25 basis points to 4.5% on May 11, 2023. Several other central banks, such as the European Central Bank, increased interest rates on main refinancing operations, the marginal lending facility and the deposit facility, each by 25 basis points, on May 10, 2023 and signalled their intention to continue to do so citing, among other factors, underlying price pressures and the high inflationary environment. Interest rates are influenced by matters other than the Federal Reserve’s monetary policy, for example volatility in the financial markets resulting from escalation of global military conflicts and higher unemployment in the U.S., the U.K. and other key markets for the Group, mean that it may be impossible to reasonably predict the course of action the Federal Reserve may take in relation to changing the federal funds rate, and interest rates may increase even if monetary policy does not change. Changes in Federal Reserve policy may also impact the overall liquidity and efficiency of fixed maturity markets. The Federal Reserve has also started to unwind the quantitative easing measures enacted to combat the effects of the COVID-19 pandemic including a reduction in the amount of assets it holds on its balance sheet. As this quantitative easing is withdrawn, financial markets may react negatively and fixed maturity market liquidity may decline, leading to heightened volatility in fixed maturity investment prices and difficulty in transacting at indicated market values.

The Group’s exposure to interest rate risk relates primarily to the changes in market price and cash flow variability of fixed maturity instruments that are associated with changes in interest rates. The Group’s

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investment portfolio contains interest rate sensitive instruments, such as fixed maturity securities which have been, and will likely continue to be, affected by changes in interest rates from central bank monetary policies, domestic and international economic and political conditions, levels of inflation and other factors beyond the Group’s control. The Group’s fixed maturity portfolio also includes asset classes such as asset-backed securities and investment grade emerging market debt, which are riskier in nature than some of the Group’s other fixed maturity instruments and could adversely impact the Group’s investment portfolio. Interest rates are highly sensitive to many factors, including governmental monetary policies, inflation, domestic and international economic and political conditions and other factors beyond the Group’s control and fluctuations could materially and adversely affect the Group’s business, financial condition and results of operations.

Steps that may be taken by central banks to raise interest rates in the future to combat higher inflation than the Group had anticipated could, in turn, lead to unrealized losses on the Group’s investments. Changes in the level of inflation could also result in an increased level of uncertainty in the estimation of loss reserves for the Group’s lines of business with a long tenor. Such changes in inflation will have the largest impact on the Group’s fixed maturity portfolio, which currently has a duration of around two years. As a result of the above factors, the Group’s business, financial condition, liquidity or operating results could be adversely affected.

Unexpected volatility or illiquidity associated with some of the Group’s investments could significantly and negatively affect the Group’s financial results, liquidity or ability to conduct business.

A small portion of the Group’s investment portfolio comprises (and may in the future continue to contain) certain investments such as structured notes linked to equities and commodities, publicly traded equities, high- yield bonds, bank loans, emerging market debt, non-agency residential mortgage-backed securities, asset-backed securities, commercial mortgage-backed securities, real estate funds, middle market loans, private credit funds, private equity funds, infrastructure funds and short-term secured products. During the height of the financial crisis of 2007 and 2008, both fixed maturity and equity markets lost significant liquidity and were more volatile than expected. The markets initially responded in a way similar to the COVID-19 pandemic, which resulted in severe falls in indices, extreme volatility and interventions to halt trading. Similar risks are present as markets respond to the ongoing Ukraine Conflict and imposition of sanctions on Russia. If the Group requires significant amounts of cash on short notice in excess of normal cash requirements, the Group may have difficulty selling investments in a timely manner or be forced to sell them for less than the Group otherwise would have been able to realize. If the Group is forced to sell the Group’s assets in unfavorable market conditions, there can be no assurance that the Group will be able to sell them for the prices at which the Group has recorded them and the Group may be forced to sell them at significantly lower prices. As a result of the above factors, the Group’s business, financial condition, liquidity or operating results could be adversely affected.

The determination of the amount of allowances and impairments taken on the Group’s investments is highly subjective and could materially impact the Group’s operating results or financial position.

The Group performs reviews of its investments on a regular basis to determine the amount of the decline in fair value below the cost basis which is considered to be the current expected credit losses in accordance with applicable accounting guidance. The process of determining the current expected credit loss (“CECL”) requires judgment and involves analyzing many factors. Assessing the accuracy of the level of allowances reflected in the Group’s financial statements is inherently uncertain, given the subjective nature of the process. Furthermore, additional impairments may need to be taken or allowances provided in the future with respect to events that may impact specific investments. The absence of CECL allowances does not necessarily mean there will not be any in the future. Future material impairments themselves or any error in accurately accounting for them may have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

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An economic downturn in the U.S. or elsewhere, the default of a large institution, an actual or predicted sovereign default, or a downgrade of U.S. or non-U.S. government securities by credit rating agencies could harm the Group’s business, investment portfolio and its liquidity and financial condition.

Weak economic conditions may adversely affect (among other aspects of the Group’s business) the demand for, and claims made under, the Group’s products; the ability of customers, counterparties and others to establish or maintain their relationships with the Group; the Group’s ability to access and efficiently use internal and external capital resources; and the Group’s investment performance. Volatility in the U.S. and other financial markets, as a result of the ongoing Ukraine Conflict on global economic conditions or otherwise, may adversely affect both the liquidity and the performance of the Group’s investments.

Furthermore, a default by one of several large institutions that are dependent on one another to meet their liquidity or operational needs or are perceived by the market to have similar financial weaknesses, so that a default by one institution causes a series of defaults by or runs on other institutions (sometimes referred to as a “systemic risk”) or a downgrade of U.S. or non-U.S. government securities by credit rating agencies, may expose the Group to investment losses which could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. For example, in March 2023, Silicon Valley Bank (“SVB”) and Signature Bank were each unable to continue their operations and the Federal Deposit Insurance Corporation (the “FDIC”) was appointed as receiver for SVB and Signature Bank. Similarly, in May 2023, the FDIC took control of First Republic Bank (“First Republic”) and JPMorgan Chase & Co. acquired a substantial amount of assets and liabilities of First Republic. Additionally, in late March 2023, Swiss authorities facilitated a merger between UBS Group AG and Credit Suisse Group AG. Although we do not have any funds deposited with these institutions, such incidents expose potential strains on the banking sector as a whole and demonstrate a heightened risk of systemic failures throughout the financial industry. An actual or predicted sovereign default may also have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

Currency fluctuations could result in exchange losses and negatively impact the Group’s business.

The Group’s functional currency is the U.S. dollar. However, because the Group’s business strategy includes insuring and reinsuring financial obligations created or incurred outside of the U.S., the Group writes a portion of its business and receives premiums in currencies other than the U.S. dollar. Consequently, the Group may experience exchange losses to the extent the Group’s foreign currency exposure is not hedged or is not sufficiently hedged, which could significantly and negatively affect the Group’s business. The Group operates in a number of countries and therefore the results of its operations are subject to both currency transaction and translation risk. Currency transaction risk arises from the mismatch of cash flows due to currency exchange fluctuations. Translation risk arises because the Group reports in U.S. dollars but a portion of its underlying premiums, reserves, operating expenses and acquisitions are determined in other currencies. The Group makes determinations as to whether and to what extent to hedge its foreign currency exposures on a monthly basis.

The Group’s investment portfolio exposures may be materially adversely affected by global climate change regulation and other factors, which could harm the Group’s business and its liquidity and financial condition.

World leaders met at the 2015 United Nations Climate Change Conference in December 2015 in Paris and agreed to limit global greenhouse gas emissions in the atmosphere to a level which would not increase the average global temperature by more than 2° Celsius, with an aspiration of limiting such increase to 1.5° Celsius (the “Paris Agreement”). In order for governments to achieve their existing and future international commitments to limit the concentration of greenhouse gases under the Paris Agreement, there is widespread consensus in the scientific community that a significant percentage of existing proven fossil fuel reserves must not be consumed. In addition, divestment campaigns, which call on asset owners to divest from direct ownership of commingled funds that include fossil fuel equities and bonds, likewise signal a change in society’s attitude towards the social and environmental externalities of doing business.

In addition, the 2021 UN Climate Change Conference (“COP26”) was held in Glasgow and sought to accelerate action towards the goals of the Paris Agreement. The COP26 agreement, although not legally binding,

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includes pledges to further cut CO2 emissions, reduce the use of coal, and significantly increase the amount of money necessary to help poor countries cope with the effects of climate change. The 2022 UN Climate Change Conference (“COP27”) was held in Sharm el-Sheikh, Egypt in November 2022. Building on the outcomes and momentum of COP26, nations were expected to demonstrate at COP27 that they are in a new era of implementation by turning their commitments under the Paris Agreement into action.

As a result of the above, energy companies and other companies engaged in the production or storage of fossil fuels may experience unexpected or premature devaluations or write-offs of their fossil fuel reserves. A material change in the asset value of fossil fuels or the securities of energy companies and companies in these related sectors may therefore materially adversely affect the Group’s investment portfolio. A material change in the asset value of fossil fuels or the securities of energy companies and companies in related sectors will impact the Fidelis investment portfolio in the event that any change in asset values leads to a shock to the wider economy and overall asset values.

Failure to meet ESG expectations or standards, or achieve ESG goals or commitments could adversely affect the Group’s business, prospects, financial condition or results of operations.

In recent years, there has been an increased focus from shareholders, business partners, cedants, regulators, politicians, and the public in general on ESG matters, including greenhouse gas emissions, carbon footprint and climate-related risks, renewable energy, fossil fuels, diversity, equity and inclusion, responsible sourcing and supply chain, human rights, and social responsibility.

The Group has established goals, commitments, and targets, as further discussed in “Business—Our Commitment to Environmental, Social and Governance Matters.” Such goals, commitments, and targets reflect the Group’s current plans and aspirations and do not guarantee that the Group will be able to achieve them. Evolving shareholder and cedant expectations, regulatory obligations or political pressures and the Group’s efforts to manage, report on and accomplish set goals present numerous operational, regulatory, reputational, financial, legal, and other risks, any of which could have a material adverse impact on the Group’s reputation, business, prospects, financial condition or results of operations.

The Group may be unable to satisfactorily meet evolving expectations, standards, regulations and disclosure requirements related to ESG. Such matters can affect the willingness or ability of investors to make an investment in FIHL, as well as the Group’s ability to meet its regulatory obligations, including compliance with any rules related to carbon footprint and greenhouse gas emissions. Negative perceptions regarding the scope or sufficiency and transparency of the Group’s commitment to and reporting on ESG matters and events that give rise to actual, potential, or perceived compliance with social responsibility matters could hurt the Group’s reputation and cause cedants to seek alternative business partners. Such loss of reputation could make it difficult and costly for the Group to regain the confidence of its business partners resulting in an adverse effect on the Group’s business, prospects, financial condition or results of operations. Further, the Group’s failure or perceived failure to satisfy various reporting standards and regulations on a timely basis, or at all, could have similar negative impacts or expose it to government enforcement actions and private litigation.

The management of the Group’s investment portfolio as a result of the Group’s sustainability principles and ESG objectives could have an adverse impact on the Group’s investment portfolio, business, financial condition, liquidity or operating results.

The Group’s investment portfolio is designed to be managed consistent with the sustainability principles and ESG objectives adopted by the Group, as further discussed in “Business—Our Commitment to Environmental, Social and Governance Matters.” As a result, the Group may forgo certain investment opportunities available to it in order to comply with such investment portfolio management criteria. This may cause the performance of the Group’s investment portfolio to differ from what it may otherwise be able to achieve if it was not managed consistent with these sustainability principles and ESG objectives.

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In addition, there is a risk that the investment opportunities identified by the Group’s asset managers as being consistent with the Group’s investment criteria do not operate as expected when addressing social and environmental impact and ESG issues. A company’s social and environmental impact and ESG performance or the Group’s asset managers’ assessment of a company’s social and environmental impact and ESG performance could vary over time, which could cause the Group to be temporarily invested in companies that do not comply with the Group’s investment criteria. Furthermore, data availability and reporting with respect to the Group’s investment criteria may not always be available or may become unreliable. If the Group’s investment decisions do not perform as expected or if the Group’s asset managers fail to make investment decisions in a manner consistent with the stated sustainability principles and ESG objectives, the Group’s investment portfolio, business, financial condition, liquidity or operating results could be adversely affected.

Risks Relating to Regulation of the Group

If the Group becomes directly subject to insurance statutes and regulations in jurisdictions other than Bermuda, the E.U. or the U.K. or there is a change to the law or regulations or application of the law or regulations of Bermuda, the E.U. or the U.K., this could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

FIBL is a registered Bermuda Class 4 insurer pursuant to the Insurance Act 1978 of Bermuda, as amended (the “Bermuda Insurance Act”), and as such, it is subject to regulation and supervision in Bermuda by the BMA. FIID operates from the Republic of Ireland and is authorized and regulated by the CBI to carry on certain classes of non-life insurance business. On the basis of its CBI authorization, FIID is able to offer its insurance services into certain European Economic Area (“EEA,” which is a free trade area including the 27 member states of the E.U. together with Iceland, Liechtenstein, and Norway) jurisdictions on a cross-border basis without the need for separate authorizations in such jurisdictions. FUL operates from the U.K. and is authorized by the PRA and regulated by the PRA and the FCA with permission to underwrite certain classes of general insurance. As FIHL is subject to Group Supervision in Bermuda, it is subject to regulation and supervision by the BMA.

The Group faces new regulatory costs and challenges as a result of the U.K.’s departure from the E.U. (“Brexit”). The U.K. and E.U. insurance prudential regimes are currently broadly identical as both derived from the Solvency II Directive. However, it is likely that the laws and regulations of the U.K. and the E.U. will diverge in the near future, and the Group may be required to utilize additional resources to ensure compliance with the different rules in each regime. In particular, the U.K. has announced that it intends to amend certain Solvency II-derived rules that it has transposed into domestic legislation and the E.U. is currently conducting its own review of the Solvency II Directive.

The U.K. has consulted with industry stakeholders on various Solvency II-derived rules since October 2020. On November 17, 2022, HM Treasury published a finalized package of proposed reforms to its prudential regime, which covers a range of areas including the risk margin, matching adjustment requirements and regulatory reporting obligations. These reforms will be reflected in new U.K. legislation and regulation during the course of 2023 and 2024. Similarly, on September 22, 2021, the European Commission published a package of proposed legislative reforms for amending the existing regulatory framework. The European Council published its agreed position on the European Commission’s proposed reforms in June 2022, which it will negotiate with the European Parliament and European Commission. The full extent of the E.U.’s changes to Solvency II will only be known once the full package of legislative reforms is finalized.

More generally, the cost of doing business in the U.K., and from the U.K. into other jurisdictions, will likely increase as a result of Brexit, and may include additional capital requirements, including as a result of new or additional laws and regulations across a wide variety of areas potentially including, but not limited to, employment laws, data privacy laws, taxation laws and the terms of commercial activities between the U.K. and the E.U. In addition, due to the potential for less inter-country cooperation between the U.K. and the E.U., both jurisdictions may be facing a less liberal trading regime in the future which could take the form of tariffs or other protectionist measures. It is also unclear how effectively supervisory bodies and regulators from these jurisdictions will continue to cooperate and share information.

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Bermuda, E.U. and U.K. insurance statutes and the regulations and policies of the BMA, the CBI, the PRA and the FCA may require FIBL, FIID and FUL to, among other things:

• maintain a minimum level of capital, surplus and liquidity;

• satisfy solvency standards;

• obtain prior approval of ownership and transfer of shares;

• maintain a principal office and appoint and maintain a principal representative in Bermuda (for FIBL), the

• Republic of Ireland (for FIID) and the U.K. (for FUL), respectively;

• maintain a head office; and

• comply with legal and regulatory restrictions with respect to their ability to pay dividends and make capital distributions upon which the Group is reliant to provide cash flow required for debt service and dividends to FIHL’s shareholders.

These statutes, regulations and policies may affect the Group’s ability to write insurance and reinsurance policies, to distribute funds around the Group and to shareholders, and to pursue its investment strategy.

The Group does not presently intend that it will create a physical presence in any jurisdiction in the U.S. The Group is not licensed to write insurance on an admitted basis in any state in the U.S. but, as an alien insurer and certified reinsurer, FIBL and FUL are eligible to write surplus lines business. However, there can be no assurance that insurance regulators in the U.S. or elsewhere will not review the activities of the Group or related companies or its agents and assert that the Group is subject to such jurisdiction’s licensing requirements. If any such assertion is successful and the Group is required to obtain a license, it may be subject to taxation in such jurisdiction. In addition, the Group is subject to indirect regulatory requirements imposed by jurisdictions that may limit its ability to provide insurance or reinsurance. For example, the Group’s ability to write insurance may be subject, in certain cases, to arrangements satisfactory to applicable regulatory bodies. Proposed legislation and regulations may have the effect of imposing additional requirements upon, or restricting the market for, alien insurers or reinsurers with whom U.S. companies place business.

Bermuda, E.U. and U.K. insurance statutes and regulations applicable to the Group may be different in scope from those that would be applicable if FIBL, FUL and/or FIID were licensed in and governed by the laws of any state in the U.S. In the past, there have been U.S. Congressional and other initiatives in the U.S. regarding proposals to supervise and regulate insurers domiciled outside the U.S. If in the future the Group becomes increasingly subject to any insurance laws of the U.S. or any state thereof or of any other jurisdiction, the Group cannot be certain that it would be in compliance with those laws or that coming into compliance with those laws would not have a significant and negative effect on its business. The process of obtaining licenses in the U.S. and elsewhere is time-consuming and costly, and FIBL, FUL or FIID may not be able to become licensed in a jurisdiction other than Bermuda, the Republic of Ireland or the U.K. should they choose to do so. The modification of the conduct of the Group’s business resulting from FIBL, FUL or FIID becoming licensed in certain jurisdictions could significantly and negatively affect its business. In addition, the Group’s inability to comply with insurance and reinsurance statutes and regulations could significantly and adversely affect its business by limiting its ability to conduct business as well as subjecting the Group to penalties and fines and having adverse reputational consequences for the Group.

The increased level of regulatory scrutiny in respect of material outsourcing arrangements in Bermuda, the E.U. and the U.K. could have a material adverse effect on the operating costs of the Group’s business and could increase the risk of disruption to the Group’s operations due to regulatory intervention.

The Framework Agreement, the Delegated Underwriting Authority Agreements and the Inter-Group Services Agreement will be regarded as “material outsourcing agreements” or “outsourcing of critical or

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important operational functions or activities” under the laws and regulation in each of the United Kingdom and the European Union. See “Certain Regulatory Considerations” for further information on material outsourcing agreements and outsourcing of critical or important operational functions or activities. Accordingly, the Group may incur additional operating costs in establishing the systems and controls required to appropriately oversee and monitor the effective performance of these agreements by Fidelis MGU.

For example, on February 6, 2020, EIOPA issued guidelines on outsourcing to cloud service providers which applied from January 1, 2021 to all cloud outsourcing arrangements entered into or amended on or after that date. Existing cloud outsourcing arrangements relating to critical or important operational functions or activities have also been reviewed and amended to ensure compliance with the guidelines by December 31, 2022. These guidelines could potentially apply to use of the Group’s information technology or application systems and infrastructure by Group companies in the EEA. This and any future regulatory developments in relation to cloud outsourcing may result in additional operating costs.

In addition, pursuant to the Insurance Act, FIBL shall not take any steps to effect a material change, including (i) outsourcing all or substantially all of its actuarial, risk management, compliance or internal audit functions, (ii) outsourcing all or a material part of its underwriting activity, and (iii) outsourcing of an officer role, unless it has first served notice on the BMA that it intends to effect such a material change and before the end of 30 days, either the BMA has notified FIBL in writing that it has no objection to such change or that the period has elapsed without the BMA having issued a notice of objection. There is a risk that the BMA may not grant its no-objection to certain new or material changes to the existing outsourcing arrangements that FIBL may propose in the future, including in relation to Framework Agreement, the Delegated Underwriting Authority Agreements or the Inter-Group Services Agreement.

Further, there has been an increased level of regulatory scrutiny of material outsourcing agreements in each jurisdiction generally, which could result in a greater risk of regulatory intervention in respect of these agreements. Such regulatory intervention may include the regulators’ use of their investigative powers (such as requiring reports to be prepared by senior individuals), the exercise of audit rights against any Group company or Fidelis MGU or requests for documents and information relating to the performance of the agreements.

These regulatory interventions could be disruptive for the Group’s business operations, and may result in the Group being required to make further changes to its systems and controls, such as increased reporting to company boards, improving data storage facilities and implementing additional oversight of Fidelis MGU. It is possible that, as a corollary, the Group will incur increased operational costs. The Group could also experience an adverse effect on its business if the regulatory interventions impede the effective operation of the Framework Agreement, the Delegated Underwriting Authority Agreements and the Inter-Group Services Agreement.

Changes to the regulatory systems or loss of authorizations, permits or licenses under which the Group operates or breach of regulatory requirements by the Group could have a material adverse effect on its business.

FIHL and FIBL (both incorporated in Bermuda), FUL (incorporated in England and Wales) and FIID (incorporated in the Republic of Ireland) may be subject to changes of law or regulation in these jurisdictions which may have an adverse impact on their operations, including the imposition of tax liabilities or increased regulatory supervision. The Group is also exposed to changes in accounting standards, some of which may be significant. In addition, FIHL, FIBL, FUL and FIID will be exposed to changes in the political environment in Bermuda, the E.U., the Republic of Ireland and the U.K. The Bermuda insurance and reinsurance regulatory framework has recently become subject to increased scrutiny in many jurisdictions, including in Europe and the U.S. and in various states within the U.S.

The Group’s ability to conduct insurance and reinsurance business in different countries generally requires the holding and maintenance of certain licenses, permissions or authorizations, and compliance with rules and

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regulations promulgated from time to time in these jurisdictions. A principal exception to this is with respect to cross border reinsurance in the U.S. and other countries.

The Group is not licensed to write insurance on an admitted basis in any state in the U.S. but, as an alien insurer and certified reinsurer, FIBL and FUL are eligible to write surplus lines business in all 50 U.S. states, the District of Columbia and other U.S. jurisdictions based on its listing in the Quarterly Listing of Alien Insurers of the International Insurers Department (“IID”) of the National Association of Insurance Commissioners (“NAIC”). Pursuant to IID requirements, the Group established a U.S. surplus lines trust fund with a U.S. bank to secure U.S. surplus lines policies. The Group accepts business only through U.S. licensed surplus lines brokers and does not market directly to the public. Failure to maintain its IID listing could have a material adverse effect on the Group’s ability to write surplus and excess lines of business in the U.S. For reinsurance there are currently no U.S. licenses required, although the Group operates outside the U.S. and is, in common with other non-U.S. reinsurers, required from time to time to post letters of credit or establish other security in order to enable U.S. cedants to take financial statement credit for liabilities ceded to members of the Group. See “Certain Regulatory Considerations—United States Insurance Regulation—FIBL’s and FUL’s U.S. Operations” for a more detailed discussion of the regulatory environment in which FIBL and FUL write surplus business lines in the U.S.

A failure to comply with rules and regulations in a jurisdiction could lead to disciplinary action, the imposition of fines or the revocation of the license, permission or authorization necessary to conduct the Group’s business in that jurisdiction, which could have a material adverse effect on the continued conduct of business and also adverse reputational consequences for the Group.

It is possible that insurance regulators in the U.S. or elsewhere may review the activities of FIHL, FIBL, FUL and FIID and assert that they are subject to such jurisdiction’s licensing requirements and require that FIHL, FIBL, FUL and/or FIID comply with additional regulatory obligations. Having to meet such requirements, however, could have a material adverse effect on the results of operations of the Group, FIBL, FUL and/or FIID. Alternatively, or in addition, any necessary changes to operations could subject FIHL, FIBL, FUL and/or FIID to taxation in the U.S. or elsewhere.

In recent years, regulation of the insurance and reinsurance industry in the U.S., the U.K., Bermuda, the E.U. and other markets in which the Group operates has been subject to significant review. These reviews have led to changes in certain legal and regulatory provisions which govern the operations of the Group, and it can be expected that further reviews and changes to applicable laws and regulations will occur in the future. The Group cannot predict the effect that any proposed or future law or regulation may have on the financial condition or results of operations of the Group. Changes in applicable laws or regulations or in their interpretation or enforcement could have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

In particular, changes in regulatory capital requirements in the U.S., the U.K., the E.U. or Bermuda may impact upon the level of capital reserves required to be maintained by individual Group entities or by the Group as a whole.

The Group may be subject to greater regulatory risk than that to which the Group is currently exposed.

In each of the jurisdictions in which the Group operates and in which the Group will operate, it has to comply with laws and regulations applicable to regulated (re)insurers. Each aspect of the regulatory environment in which the Group operates and in which the Group will operate is subject to change, which may be retrospective. Complying, or failing to comply, with existing and new regulations could result in additional costs for the Group, which could have an adverse effect (including to a material extent) on the financial condition or results of operations of the Group.

Data protection failures could disrupt the Group’s business, damage its reputation and cause losses.

Since May 25, 2018, the European General Data Protection Regulation (the “E.U. GDPR”) has been directly applicable in all E.U. member states. The U.K.’s General Data Protection Regulation and Data Protection

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Act 2018 (collectively, the “U.K. GDPR”) is the retained E.U. law version of E.U. GDPR (the U.K. GDPR and the E.U. GDPR collectively, the “GDPR”). The Group is subject to the GDPR when offering goods and services to E.U. and/or U.K.-based data subjects, as applicable (regardless of whether through Group companies in the E.U. and/or the U.K.). The GDPR imposes comprehensive data privacy compliance obligations in relation to our collection, processing, sharing, disclosure, transfer and other use of data relating to an identifiable living individual or “personal data,” as applicable, including: the obligation to appoint data protection officers in certain circumstances; new rights for individuals to be “forgotten” and rights to data portability; the principle of accountability; and the obligation to make public notification of significant data breaches. The GDPR also retains and adds to existing requirements, including restrictions on transfers of personal data outside of the EEA/U.K., as applicable, and the requirement to include specific data protection provisions in agreements with data processors.

The GDPR also regulates cross-border transfers of personal data out of the EEA and the U.K. Recent legal developments in Europe have created complexity and uncertainty regarding such transfers, in particular in relation to transfers to the United States. On July 16, 2020, the Court of Justice of the European Union (the “CJEU”) invalidated the E.U.-U.S. Privacy Shield Framework, or Privacy Shield, under which personal data could be transferred from the EEA (and the U.K.) to relevant self-certified U.S. entities. The CJEU further noted that reliance on the standard contractual clauses (a standard form of contract approved by the European Commission as an adequate personal data transfer mechanism and potential alternative to the Privacy Shield) alone may not necessarily be sufficient in all circumstances and that transfers must be assessed on a case-by-case basis. Subsequent European court and regulator decisions have taken a restrictive approach to international data transfers. As the enforcement landscape further develops, and supervisory authorities issue further guidance on—and revised standard contractual clauses for—international data transfers, we could suffer additional costs, complaints and/or regulatory investigations or fines; we may have to stop using certain tools and vendors and make other operational changes which could otherwise affect the manner in which we provide our services, and could adversely affect our business, operations and financial condition.

We are also subject to evolving E.U. and U.K. privacy laws on cookies, tracking technologies and e-marketing. Recent European court and regulator decisions are driving increased attention to cookies and similar tracking technologies. In the E.U. and U.K., informed consent is required for the placement of certain cookies or similar tracking technologies on an individual’s device and for direct electronic marketing. Consent is tightly defined and includes a prohibition on pre-checked consents and a requirement to obtain separate consents for each type of cookie or similar technology. If the trend of increasing enforcement by regulators of the strict approach to opt-in consent for all but essential use cases, as seen in recent guidance and decisions continues, this could lead to substantial costs, require significant systems changes, limit the effectiveness of our marketing activities, divert the attention of our technology personnel, adversely affect our margins, and subject us to additional liabilities. In light of the complex and evolving nature of E.U., E.U. member state and U.K. privacy laws on cookies and tracking technologies, there can be no assurances that we will be successful in our efforts to comply with such laws; violations of such laws could result in regulatory investigations, fines, orders to cease/ change our use of such technologies, as well as civil claims including class actions, and reputational damage.

Since we are under the supervision of relevant data protection authorities in both the EEA and the U.K., we may be fined under both the E.U. GDPR and U.K. GDPR for the same breach. Penalties for certain breaches are up to the greater of EUR 20 million/ GBP 17.5 million or 4% of our global annual turnover. In addition to fines, a breach of the GDPR may result in regulatory investigations, reputational damage, orders to cease/ change our data processing activities, enforcement notices, assessment notices for a compulsory audit and/or civil claims (including class actions).

Bermuda introduced the Personal Information Protection Act 2016 (“PIPA”) in 2016 to regulate and protect the use of personal information. PIPA applies to any organization (meaning any individual, entity or public authority) that uses personal information in Bermuda where that personal information is used by automated or other means which form, or are intended to form, part of a structured filing system. Under PIPA “personal information” means any information about an identified or identifiable individual (meaning a natural person), and “use” is broadly defined to include carrying out any operation on or possessing personal information.

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Only certain limited sections of PIPA came into force in 2016, and at present the only operative sections relate to interpretations, citation and commencement and certain provisions in respect of the establishment and operation of the Privacy Commissioner’s Office. The principal sections of PIPA, which include: conditions for use and consent to use of personal information, obligations on organizations that use personal information, data transfer and protection obligations and access, rectification and erasure rights for individuals, are not yet in force. The references to PIPA provisions below are provisions which are not yet in force. It is anticipated that such provisions will phase into operation in the near future, and to the extent that the Group uses or holds individuals’ personal information in Bermuda, the Group will need to comply with such in force PIPA provisions.

In general, an organization must adopt suitable measures and policies to give effect to its obligations and to the rights of individuals set out in PIPA, and may only use an individual’s personal information where one or more of the prescribed conditions for use is met. Organizations must designate a privacy officer, and must provide individuals with a clear and easily accessible statement about its personal information practices and policies, which must include: the fact that personal information is being used; the purposes for which personal information is or might be used; the identity and types of individuals or organizations to whom personal information might be disclosed; the identity and location of the organization, including information on how to contact it about its handling of personal information; the name of the privacy officer; and the choices and means the organization provides to an individual for limiting the use of, and for accessing, rectifying, blocking, erasing and destroying, their personal information.

Personal information held by an organization must be adequate, relevant and not excessive in relation to the purposes for which it is used, and must be accurate and kept up to date to the extent necessary for its use. An organization must protect personal information that it holds with appropriate and proportional safeguards against risk, including loss; unauthorized access, destruction, use, modification or disclosure; or any other misuse.

Where an organization engages (by contract or otherwise) the services of a third party in connection with the use of personal information, including transfers to overseas third parties, the organization remains responsible at all times for ensuring compliance with PIPA.

Oversight and enforcement of PIPA is the responsibility of Bermuda’s Privacy Commissioner. The Privacy Commissioner has certain investigatory, order making and enforcement powers, including issuing formal warnings, public admonishment or disclosure for prosecution for offenses under PIPA, including corporate offenses committed with the consent or connivance of corporate officers, which could result in a fine or imprisonment.

Other than the above, continuing regulatory developments in the national laws and regulations of individual E.U. member states, the U.K. and Bermuda in relation to the processing of personal data, has increased and may continue to increase the Group’s compliance obligations and has necessitated and may continue to necessitate the review and implementation of updated policies and processes relating to the Group’s collection and use of personal data. Any further and/or ongoing increase in compliance obligations could also lead to increased compliance costs, which may have an adverse impact on the Group’s business, prospects, financial condition or results of operations.

If any person, including any of the Group’s employees or those with whom the Group shares personal data, negligently disregards or intentionally breaches the Group’s established controls with respect to personal data that the Group holds, the Group could be subject to significant monetary damages, regulatory enforcement actions, fines and/or criminal prosecution in one or more jurisdictions. In addition, a data breach could result in negative publicity, which could damage the Group’s reputation and have an adverse effect on the Group’s business, prospects, financial condition or results of operations.

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The Group is required to comply with the applicable economic and trade sanctions laws and regulations. The Group’s failure to comply with these laws and regulations would have an adverse effect on our business, financial condition and results of operations.

The Group is required to comply with all applicable economic and trade sanctions laws and regulations. Various governmental authorities with jurisdiction over the Group’s activities maintain economic and trade sanctions laws and regulations, which restrict the Group’s ability to conduct transactions and dealings with certain countries, territories, persons and entities. While the Group maintains policies and procedures designed to maintain compliance with economic and trade sanctions, the Group cannot guarantee that the policies and procedures will be effective in preventing violations or allegations of violations. Violations, or allegations of violations, could result in civil and criminal penalties, including fines for the Group or incarceration for responsible employees and managers, as well as negative publicity or reputational harm.

Risks Relating to Taxation—U.S. Tax Risks

For purposes of this discussion, the term “U.S. Person” means: (i) an individual citizen or resident of the U.S., (ii) a partnership or corporation, created in or organized under the laws of the U.S., or organized under the laws of any political subdivision thereof, (iii) an estate the income of which is subject to U.S. federal income taxation regardless of its source, or (iv) a trust if either (x) a court within the U.S. is able to exercise primary supervision over the administration of such trust and one or more U.S. Persons have the authority to control all substantial decisions of such trust, or (y) the trust has a valid election in effect under applicable U.S. Treasury Regulations to be treated as a U.S. Person for U.S. federal income tax purposes or (z) any other person or entity that is treated for U.S. federal income tax purposes as if it were one of the foregoing. For purposes of this discussion, the term “U.S. Holder” means a U.S. Person other than a partnership, who beneficially owns Common Shares.

U.S. Tax Reform

The Tax Cuts and Jobs Act (the “2017 Act”) was passed by the U.S. Congress and signed into law on December 22, 2017, with certain provisions intended to eliminate certain perceived tax advantages of companies (including insurance companies) that have legal domiciles outside the U.S., but have certain U.S. connections, and U.S. Persons (as defined below) investing in such companies. Among other things, the 2017 Act revised the rules applicable to passive foreign investment companies (“PFICs”) and controlled foreign corporations (“CFCs”) in ways that could affect the timing or amount of U.S. federal income taxes imposed on certain investors that are U.S. Persons. Further, it is possible that other legislation could be introduced and enacted by the current Congress or future Congresses that could have an adverse impact on the Group, the Group’s operations or U.S. Holders. Additionally, tax laws and interpretations regarding whether a company is engaged in a U.S. trade or business or whether a company is a CFC or a PFIC or has related person insurance income (“RPII”) are subject to change, possibly on a retroactive basis. The Treasury Department recently issued final and proposed regulations intended to clarify the application of the insurance income exception to the classification of a non-U.S. insurer as a PFIC and provide guidance on a range of issues relating to PFICs, and recently issued proposed regulations that would expand the scope of the RPII rules. New regulations or pronouncements interpreting or clarifying such rules may be forthcoming as well. FIHL cannot be certain if, when, or in what form such regulations or pronouncements may be provided and whether such guidance will have a retroactive effect.

FIHL and/or its non-U.S. subsidiaries may be subject to U.S. federal income taxation.

A non-U.S. corporation that is engaged in the conduct of a U.S. trade or business will be subject to U.S. federal income tax as described below, unless entitled to the benefits of an applicable tax treaty. Whether a trade or business is being conducted in the U.S. is an inherently factual determination. As the Internal Revenue Code of 1986, as amended (the “Code”), regulations and court decisions fail to identify definitively activities that constitute being engaged in a trade or business in the U.S., the Group cannot be certain that the Internal Revenue Service (“IRS”) will not contend successfully that FIHL and/or its non-U.S. subsidiaries are or will be engaged

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in a trade or business in the U.S. A non-U.S. corporation deemed to be so engaged would be subject to U.S. income tax at regular corporate rates on the portion of its income that is treated as effectively connected with the conduct of that U.S. trade or business (“ECI”), as well as the branch profits tax on its dividend equivalent amount (generally, the ECI (with certain adjustments) deemed withdrawn from the U.S.), unless the corporation is entitled to relief under the permanent establishment provision of an applicable tax treaty. Any such U.S. federal income taxation could result in substantial tax liabilities and could have a material adverse effect on the results of operation of FIHL and its non-U.S. subsidiaries.

Non-U.S. corporations not engaged in a trade or business in the U.S. are nonetheless subject to U.S. income tax imposed by withholding on certain “fixed or determinable annual or periodic gains, profits and income” derived from sources within the U.S. (such as dividends and certain interest on investments), subject to exemption under the Code or reduction by applicable treaties.

The U.S. also imposes an excise tax on insurance and reinsurance premiums (“FET”) paid to non-U.S. insurers or reinsurers that are not eligible for the benefits of a U.S. income tax treaty that provides for an exemption from the FET with respect to risks (i) of a U.S. entity or individual, located wholly or partially within the U.S. and (ii) of a non-U.S. entity or individual engaged in a trade or business in the U.S., located within the U.S. The rates of tax are 4% for property casualty insurance premiums and 1% for reinsurance premiums.

U.S. Holders will be subject to adverse tax consequences if FIHL is considered a PFIC for U.S. federal income tax purposes.

In general, a non-U.S. corporation will be a PFIC during a given year if (i) 75% or more of its gross income constitutes “passive income” (the “75% test”) or (ii) 50% or more of its assets produce (or are held for the production of) passive income (the “50% test”). If FIHL were characterized as a PFIC during a given year, each U.S. Holder would be subject to a penalty tax at the time of the taxable disposition at a gain of, or receipt of, an “excess distribution” with respect to, their shares, unless such person is a 10% U.S. Shareholder (as defined below) subject to tax under the CFC rules or such person made a “qualified electing fund” (“QEF”) election or, if the Common Shares are treated as “marketable stock” in such year, such person made a mark-to-market election. In addition, if FIHL were considered a PFIC, upon the death of any U.S. individual owning shares such individual’s heirs or estate would not be entitled to a “step-up” in the basis of the shares that might otherwise be available under U.S. federal income tax laws. In addition, a distribution paid by FIHL to U.S. Holders that is characterized as a dividend and is not characterized as an excess distribution would not be eligible for reduced rates of tax as qualified dividend income if FIHL were considered a PFIC in the taxable year in which such dividend is paid or in the preceding taxable year. A U.S. Person that is a shareholder in a PFIC may also be subject to additional information reporting requirements, including the filing of an IRS Form 8621.

For the above purposes, passive income generally includes interest, dividends, annuities and other investment income. The PFIC rules provide that income derived in the active conduct of an insurance business by a qualifying insurance corporation is not treated as passive income (the “insurance income exception”). The PFIC provisions also contain a look-through rule under which a foreign corporation will be treated, for purposes of determining whether it is a PFIC, as if it “received directly its proportionate share of the income…” and as if it “held its proportionate share of the assets…” of any other corporation in which it owns at least 25% of the value of the stock (the “look-through rule”). Under the look-through rule, FIHL should be deemed to own its proportionate share of the assets and to have received its proportionate share of the income of its non-U.S. insurance subsidiaries for purposes of the 75% test and the 50% test. However, the 2017 Act limits the insurance income exception to a non-U.S. insurance company that is a qualifying insurance corporation that would be taxable as an insurance company if it were a U.S. corporation and maintains insurance liabilities of more than 25% of such company’s assets for a taxable year (the “25% Test”) (or maintains insurance liabilities that at least equal or exceed 10% of its assets, is predominantly engaged in an insurance business and satisfies a facts-and-circumstances test that requires a showing that the failure to exceed the 25% threshold is due to runoff-related or rating-related circumstances (the “10% Test,” together with the 25% Test, the “Reserve

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Test”)). The Group believes that FIBL has met this Reserve Test and will continue to do so in the foreseeable future, in which case FIHL would not be expected to be a PFIC, although no assurance may be given that FIBL will satisfy the Reserve Test in future years.

Further, the Treasury Department recently issued final and proposed regulations intended to clarify the application of the insurance income exception to the classification of a non-U.S. insurer as a PFIC and provide guidance on a range of issues relating to PFICs, including the application of the look-through rule, the treatment of income and assets of certain U.S. insurance subsidiaries for purposes of the look-through rule and the extension of the look-through rule to 25%-or-more-owned partnerships (the “2020 Regulations”). The 2020 Regulations define insurance liabilities for purposes of the Reserve Test, and tighten the Reserve Test as well as place a statutory cap on insurance liabilities, and provide guidance on the runoff-related and rating-related circumstances for purposes of the 10% Test. The 2020 Regulations, which set forth in proposed form certain requirements that must be met to satisfy the “active conduct of an insurance business” test, also propose that a non-U.S. insurer with no or a nominal number of employees that relies exclusively or almost exclusively upon independent contractors (other than related entities) to perform its core functions will not be treated as engaged in the active conduct of an insurance business. Further, for purposes of applying the 10% Test, the 2020 Regulations: (i) generally limit the rating-related circumstances exception to a non-U.S. corporation: (a) if more than half of such corporation’s net written premiums for the applicable period are derived from insuring catastrophic risk, or (b) providing certain other insurance coverage that the Group is not expected to engage in, and (ii) reduce a corporation’s insurance liabilities by the amount of any reinsurance recoverable relating to such liability. The Group believes that, based on the implementation of its business plan and the application of the look-through rule and the exceptions set out under Section 1297 of the Code, none of the income and assets of FIBL should be treated as passive pursuant to the 10% Test, and thus FIHL should not be characterized as a PFIC under current law for the current taxable year or for foreseeable future years to the extent a shareholder makes an election to apply the 10% Test, but because of the legal uncertainties as well as factual uncertainties with respect to the Group’s planned operations, there is a risk that FIHL will be characterized as a PFIC for U.S. federal income tax purposes. In addition, because of the legal uncertainties relating to how the 2020 Regulations will be interpreted and the form in which the proposed 2020 Regulations may be finalized, no assurance can be given that FIHL will not qualify as a PFIC under final IRS guidance or any future regulatory proposal or interpretation that may be subsequently introduced and promulgated. If FIHL is considered a PFIC, it could have material adverse tax consequences for an investor that is subject to U.S. federal income taxation. Prospective investors should consult their tax advisors as to the effects of the PFIC rules.

As noted above, the 10% Test will only apply if a U.S. Holder makes a valid election. A U.S. Holder seeking to elect the application of the 10% Test FIBL may do so if the Group provides the holder with, or otherwise makes publicly available, a statement or other disclosure that FIBL meet the requirements of the 10% Test (and contains certain other relevant information). The Group intends to either provide each U.S. investor with such a statement or otherwise make such a statement publicly available. A U.S. Holder may generally make an election to apply the 10% Test by completing a Form 8621 and attaching it to its original or amended U.S. federal income tax return for the taxable year to which the election relates. Investors owning a de minimis amount of FIHL stock may be deemed to have made the election automatically. U.S. Holders are urged to consult their tax advisors regarding electing to apply the 10% Test to FIBL.

U.S. Holders are also urged to consult with their tax advisors and to consider making a “protective” QEF election with respect to FIHL and each of FIHL’s non-U.S. subsidiaries to preserve the possibility of making a retroactive QEF election. If the Group determines that FIHL is a PFIC, the Group intends to use commercially reasonable efforts to provide the information necessary to make a QEF election for FIHL and each non-U.S. subsidiary of FIHL that is a PFIC. A U.S. Person that makes a QEF election with respect to a PFIC is currently taxable on its pro rata share of the ordinary earnings and net capital gain of such company during the years it is a PFIC (at ordinary income and capital gain rates, respectively), regardless of whether or not distributions were received. In addition, any of the PFIC’s losses for a taxable year will not be available to U.S. Persons and may not be carried back or forward in computing the PFIC’s ordinary earnings and net capital gain in other taxable

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years. U.S. Holders are also urged to consult with their tax advisors regarding the availability and consequences of making a mark-to-market election with respect to FIHL, although there can be no assurance that such election will be available, and such election likely would not be available for any subsidiary of FIHL also treated as a PFIC. In general, if a U.S. Holder were to make a timely and effective mark-to-market election, such holder would include as ordinary income each year the excess, if any, of the fair market value of the holder’s Common Shares at the end of the taxable year over its adjusted basis in the Common Shares. Any gain recognized by such holder on the sale or other disposition of the Common Shares would be ordinary income, and any loss would be an ordinary loss to the extent of the net amount of previously included income as a result of the mark-to-market election and, thereafter, a capital loss. U.S. Holders considering a mark-to-market election for FIHL should consult with their tax advisors regarding making a QEF election for any non-U.S. subsidiary of FIHL treated as a PFIC.

U.S. Holders of 10% or more of FIHL’s Common Shares may be subject to U.S. income taxation under the CFC rules.

Each 10% U.S. Shareholder of a non-U.S. corporation that is a CFC during a taxable year and that owns shares in the CFC, directly or indirectly through non-U.S. entities, on the last day of the non-U.S. corporation’s taxable year that the non-U.S. corporation is a CFC, generally must include in its gross income for U.S. federal income tax purposes its pro rata share of the CFC’s “subpart F income,” and global intangible low taxed income (“GILTI”) even if the subpart F income or GILTI is not distributed. A non-U.S. corporation is considered a CFC if 10% U.S. Shareholders own (directly, indirectly through non-U.S. entities or by attribution by application of the constructive ownership rules of Section 958(b) of the Code (i.e., “constructively”)) more than 50% of the total combined voting power of all classes of stock of such non-U.S. corporation, or more than 50% of the total value of all stock of such corporation. For purposes of taking into account insurance income, which is a category of subpart F income, a CFC also includes a non-U.S. corporation that earns insurance income in which more than 25% of the total combined voting power of all classes of stock or more than 25% of the total value of all stock is owned by 10% U.S. Shareholders on any day of the taxable year of such corporation, if the gross amount of premiums or other consideration for the reinsurance or the issuing of insurance or annuity contracts exceeds 75% of the gross amount of all premiums or other consideration in respect of all risks. A “10% U.S. Shareholder” is a U.S. Person who owns (directly, indirectly through non-U.S. entities or constructively) at least 10% of the total combined voting power or value of all classes of stock of the non-U.S. corporation.

FIHL believes that because of the anticipated dispersion of ownership of FIHL’s Common Shares no U.S. Holder of FIHL should be treated as owning (directly, indirectly through non-U.S. entities or constructively) 10% or more of the total voting power or value of FIHL. However, because FIHL’s Common Shares may not be as widely dispersed as the Group believes due to, for example, the application of certain ownership attribution rules, no assurance may be given that a U.S. Person who owns directly, indirectly or constructively, FIHL’s Common Shares will not be characterized as a 10% U.S. Shareholder, in which case such U.S. Person may be subject to taxation under the CFC rules.

U.S. Persons who own or are treated as owning Common Shares may be subject to U.S. income taxation at ordinary income rates on their proportionate share of the Group’s RPII.

If (i) a non-U.S. subsidiary of FIHL is 25% or more owned (by vote or value) directly, indirectly through non-U.S. entities or constructively by U.S. Persons that hold shares of FIHL directly or indirectly through foreign entities, (ii) the RPII (determined on a gross basis) of the non-U.S. subsidiary were to equal or exceed 20% of the non-U.S. subsidiary’s gross insurance income in any taxable year and (iii) direct or indirect insureds (and persons related to those insureds) own directly or indirectly through entities 20% or more of the voting power or value of the non-U.S. subsidiary, then a U.S. Person who owns any shares of the non-U.S. subsidiary (directly or indirectly through non-U.S. entities, including by holding Common Shares) on the last day of the taxable year would be required to include in its income for U.S. federal income tax purposes such person’s pro rata share of the non-U.S. subsidiaries’ RPII for the entire taxable year, determined as if such RPII were distributed

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proportionately only to U.S. Persons at that date regardless of whether such income is distributed, in which case the U.S. Person’s investment could be materially adversely affected. Generally, RPII is any “insurance income” (as defined below) attributable to policies of insurance or reinsurance with respect to which the person (directly or indirectly) insured is an “RPII shareholder” (as defined below) or a related person to such RPII shareholder. The amount of RPII earned by the non-U.S. subsidiary (generally, premium and related investment income from the direct or indirect insurance or reinsurance of any RPII shareholder or any person related to such RPII shareholder) will depend on a number of factors, including the identity of persons directly or indirectly insured or reinsured by the non-U.S. subsidiary. FIHL believes that the direct or indirect insureds of its non-U.S. subsidiaries (and related persons), whether or not U.S. Persons, should not directly or indirectly own 20% or more of either the voting power or value of the shares of FIHL or other non-U.S. subsidiaries immediately after the consummation of this offering and FIHL does not expect this to be the case in the foreseeable future (the “20% Ownership Exception”). Additionally, FIHL does not expect the gross RPII of any non-U.S. subsidiary to equal or exceed 20% of its gross insurance income in any taxable year for the foreseeable future (the “20% Gross Income Exception”), but cannot be certain that this will be the case because some of the factors which determine the extent of RPII may be beyond the Group’s control. Further, recently proposed regulations could, if finalized in their current form, substantially expand the definition of RPII to include insurance income of FIHL’s non-U.S. subsidiaries with respect to certain affiliate reinsurance transactions. If these proposed regulations are finalized in their current form, it could limit the Group’s ability to execute affiliate reinsurance transactions that would otherwise be undertaken for non-tax business reasons in the future and could increase the risk that the 20% Gross Income Exception would not be met for one or more of FIHL’s non-U.S. subsidiaries in a particular taxable year, which could result in such RPII being taxable to U.S. Persons that own or are treated as owning Common Shares. Prospective investors are urged to consult their tax advisors with respect to these rules.

U.S. tax-exempt organizations that own Common Shares may recognize unrelated business taxable income.

Tax-exempt entities will be required to treat certain subpart F insurance income, including RPII, that is includable in income by the tax-exempt entity as unrelated business taxable income. Prospective investors that are tax exempt entities are urged to consult their tax advisors as to the potential impact of the unrelated business taxable income provisions of the Code.

U.S. Holders who dispose of shares may be subject to U.S. federal income taxation at the rates applicable to dividends on a portion of such disposition.

Subject to the discussion above relating to the potential application of PFIC rules, Code 1248 may apply to a disposition of Common Shares. Code Section 1248 provides that if a U.S. Person sells or exchanges stock in a non-U.S. corporation and such person owned, directly, indirectly through certain non-U.S. entities or constructively, 10% or more of the voting power of the corporation at any time during the five-year period ending on the date of disposition when the corporation was a CFC, any gain from the sale or exchange of the shares will be treated as a dividend to the extent of the CFC’s earnings and profits (determined under U.S. federal income tax principles) during the period that the shareholder held the shares and while the corporation was a CFC (with certain adjustments). FIHL believes that because of the anticipated dispersion of ownership of FIHL’s Common Shares and provisions in its organizational documents that are intended to limit voting power in certain circumstances, no U.S. Holder of the Common Shares should be treated as owning (directly, indirectly through non-U.S. entities or constructively) 10% or more of the total voting power of FIHL; to the extent this is the case, the application of Code Section 1248 under the regular CFC rules should not apply to dispositions of the Common Shares. However, because the Common Shares may not be as widely dispersed as FIHL believes due to, for example, the application of certain ownership attribution rules, and the provisions in FIHL’s organizational documents described above have not been tested, no assurance may be given that a U.S. Holder will not be characterized as owning, directly, indirectly through certain non-U.S. entities or constructively, 10% or more of the voting power of FIHL, in which case such U.S. Holder may be subject to Code Section 1248 rules.

Additionally, Code Section 1248, in conjunction with the RPII rules, also applies to the sale or exchange of shares in a non-U.S. corporation if the non-U.S. corporation would be treated as a CFC for RPII purposes

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regardless of whether the shareholder owns, directly, indirectly through certain non-U.S. entities or constructively, 10% or more of the voting power of such non-U.S. corporation or the 20% Gross Income Exception or 20% Ownership Exception applies. Existing proposed regulations do not address whether Code Section 1248 would apply if a non-U.S. corporation is not a CFC but the non-U.S. corporation has a subsidiary that would be treated as a CFC for RPII purposes. FIHL believes, however, that this application of Code Section 1248 under the RPII rules should not apply to dispositions of Common Shares because FIHL will not be directly engaged in the insurance business. FIHL cannot be certain, however, that the IRS will not interpret the proposed regulations in a contrary manner or that the Treasury Department will not amend the proposed regulations to provide that these rules will apply to dispositions of Common Shares. Prospective investors should consult their tax advisors regarding the effects of these rules on a disposition of Common Shares.

Dividends from FIHL may not satisfy the requirements for “qualified dividend income,” and therefore may not be eligible for the reduced rates of U.S. federal income tax applicable to such income.

Non-corporate U.S. Holders, including individuals, generally will be subject to U.S. federal income taxation at a current maximum rate of 37% (not including the Medicare contribution tax) upon their receipt of dividend income from FIHL unless such dividends constitute “qualified dividend income” (as defined in the Code) (“QDI”). QDI received by non-corporate U.S. Holders meeting certain holding requirements from domestic corporations or “qualified foreign corporations” is subject to tax at long-term capital gains rates (up to a maximum of 20%, not including the Medicare contribution tax). Dividends paid by FIHL generally may constitute QDI if (i) FIHL is able to claim benefits under the income tax treaty between the U.S. and the U.K. (the “U.K. Tax Treaty”) or the Common Shares are readily tradable on an established securities market in the U.S., and (ii) FIHL is not treated as a PFIC for the taxable year such dividends are paid and the preceding taxable year. Under current U.S. Treasury Department guidance, the Common Shares would be treated as readily tradeable on an established securities market if they are listed on NYSE, as we intend the Common Shares to be after this offering. However, there can be no assurance that our Common Shares will continue to be listed on NYSE or that FIHL will not be treated as a PFIC for any taxable year.

Prospective investors are advised to consult their own tax advisors with respect to the application of these rules.

Information regarding a U.S. Holder’s identity may be reported to the relevant tax authority to ensure compliance with the U.S. Foreign Account Tax Compliance Act (“FATCA”) and similar regimes.

Under FATCA, the U.S. imposes a withholding tax of 30% on U.S.-source interest, dividends and certain other types of income which are received by a foreign financial institution (“FFI”), unless such FFI enters into an agreement with the IRS to obtain certain information as to the identity of the direct and indirect owners of accounts in such institution. Withholding on U.S.-source interest, dividends and certain other types of income applies currently, and proposed U.S. Treasury regulations provide that this withholding will not apply to gross proceeds.

Alternatively, a 30% withholding tax may be imposed on the above payments to certain passive non-financial foreign entities (“NFFE”) which do not (i) certify to each respective withholding agent that they have no “substantial U.S. owners” (i.e., a U.S. 10% direct or indirect shareholder), or (ii) provide such withholding agent with the certain information as to the identity of such substantial U.S. owners.

FIHL believes and intends to take the position that it will be an NFFE, and not an FFI, although no assurance can be given that the IRS would not assert, or that a court would not uphold, a different characterization of FIHL.

The U.K. has signed an intergovernmental agreement (“IGA”) with the U.S. (the “U.K. IGA”), and Bermuda has signed a Model 2 IGA with the U.S. (the “Bermuda IGA”) directing Bermuda FFIs to enter into agreements

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with the IRS to comply with FATCA. FIHL and FUL intend to comply with the U.K. IGA and Bermuda IGA and/or FATCA, as applicable, and FIBL intends to comply with the Bermuda IGA and/or FATCA, as applicable. Each of FIHL, FIBL and FUL will report all necessary information regarding substantial U.S. owners to the relevant authority. Any substantial U.S. owner will be required to use commercially reasonable best efforts to provide such identifying information, subject to reasonable confidentiality provisions that do not prohibit the disclosure of information reasonably required by FIHL, as is required to enable the company to comply. Shareholders who fail to provide such information could be subject to: (i) a forced sale of their Common Shares; or (ii) a redemption of their Common Shares. Should FIHL determine that it is an FFI, FIHL will report all necessary information regarding all U.S. Holders of the Common Shares.

Risks Relating to Taxation—U.K. Tax Risks

Any change in FIHL’s tax status or any change in U.K. tax laws could materially affect the Group’s business, prospects, financial condition or results of operations or ability to provide returns to shareholders.

FIHL is not incorporated in the U.K. but has filed returns for U.K. corporation tax on the basis that it is resident in the U.K. since August 2015. FIHL and the U.K.-incorporated companies within the Group are subject to U.K. tax in respect of their worldwide income and gains (subject to any applicable exemptions), which represent a material portion of the Group’s income and operations. Any change in FIHL’s tax status or any change in U.K. tax laws could materially affect the Group’s business, prospects, financial condition or results of operations or ability to provide returns to shareholders.

FIBL may be subject to U.K. tax, in which case its results of operations could be materially adversely affected.

FIBL is not incorporated in the U.K. and, accordingly, should not be treated as being resident in the U.K. for corporation tax purposes unless its central management and control is exercised in the U.K. The concept of central management and control is indicative of the highest level of control of a company, which is wholly a question of fact. The directors of FIBL intend to manage its affairs so that it is not resident in the U.K. for U.K. tax purposes as a result of the central management and control of FIBL being outside of the U.K.

A company that is not resident in the U.K. for corporation tax purposes can nevertheless be subject to U.K. corporation tax if it carries on a trade through a permanent establishment in the U.K., but, in that situation, the charge to U.K. corporation tax is limited to profits (both revenue profits and capital gains) attributable directly or indirectly to such permanent establishment.

The directors of FIBL intend to operate FIBL in such a manner that FIBL does not carry on a trade through a permanent establishment in the U.K. Nevertheless, because neither case law nor U.K. statute provides a clear definition as to the activities that constitute trading in the U.K. through a permanent establishment, His Majesty’s Revenue and Customs (“HMRC”) might contend successfully that FIBL is trading in the U.K. through a permanent establishment in the U.K.

The U.K. has no comprehensive income tax treaty with Bermuda. There are circumstances in which companies that are neither resident in the U.K. nor entitled to the protection afforded by a double tax treaty between the U.K. and the jurisdiction in which they are resident may be exposed to income tax in the U.K. (other than by deduction or withholding) on the profits of a trade carried on in the U.K. even if that trade is not carried on through a permanent establishment. However, the directors of FIBL intend to operate FIBL in such a manner that FIBL will not fall within the charge to income tax in the U.K. (other than by deduction or withholding).

If FIBL were treated as being resident in the U.K. for U.K. corporation tax purposes, or as carrying on a trade in the U.K., the results of the Group’s operations could be materially adversely affected.

The U.K. diverted profits tax (“DPT”) may apply in a situation where (i) an entity carries on activity in the U.K. in connection with the business of a non-U.K. resident company in circumstances where that entity does not

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constitute a U.K. permanent establishment of the non-U.K. company, (ii) it is reasonable to assume that an entity’s activities are designed to ensure that the non-U.K. resident company does not carry on a trade in the U.K. and (iii) one of the main purposes of the arrangements is the avoidance of U.K. corporation tax. DPT is charged at a higher rate than U.K. corporation tax and will remain at a higher rate following the increase in line with the U.K. corporation tax rate on April 1, 2023. If it applies, the results of the Group’s operations could be materially adversely affected.

Although the DPT is a relatively new tax and the statute and HMRC guidance are largely untested in the U.K. courts, the Group is of the view that the DPT is not applicable to the Group and does not intend to notify HMRC of any liability to DPT for the current or any preceding years.

Risks Relating to Taxation—Irish Tax Risks

FIID may be treated as being resident for tax purposes in a jurisdiction other than Ireland, which could negatively impact the Group’s results of operations.

• Under Irish tax law, a company which is incorporated in Ireland is automatically resident for tax purposes in Ireland. The one exception is that an Irish-incorporated company will not be resident for tax purposes in Ireland if it is treated as resident for tax purposes in another jurisdiction under the terms of a double tax treaty which has the force of law.

• FIID is incorporated in Ireland. As a result, FIID is automatically resident for tax purposes in Ireland, unless it is treated as resident elsewhere under the terms of a double tax treaty. The directors of FIID carry on (and intend to continue to carry on) FIID’s business in a manner which ensures that it is resident for tax purposes solely in Ireland. For example, a majority of FIID’s directors are resident in Ireland and FIID’s board meetings are convened in Ireland, with a majority of such directors in physical attendance. Nevertheless, there can be no guarantee that another jurisdiction will not assert that FIID is tax-resident in their jurisdiction. If FIID were treated as being resident for tax purposes in another jurisdiction, its profits may be subject to comprehensive taxation in that other jurisdiction and the results of the Group’s operations could be materially adversely affected.

• FIID’s directors also carry on (and intend to continue to carry on) FIID’s business in a manner which ensures that it does not have a permanent establishment in any jurisdiction and its profits are only subject to tax in Ireland as a result. It is possible that non-Irish agents or brokers distributing insurance underwritten by FIID could create permanent establishments outside of Ireland if they were not considered agents who are independent of FIID from a legal and economic perspective. The treatment of any agents as dependent agents may result in the creation of permanent establishments outside of Ireland to which FIID must allocate profits for tax purposes, resulting in such profits being subject to comprehensive taxation in that other jurisdiction and the results of the Group’s operations being materially adversely affected.

Any adverse adjustment to Irish tax law or the Irish Revenue Commissioners’ interpretation of the scope of an Irish value-added tax (“VAT”) group may give rise to additional irrecoverable Irish VAT cost, which could negatively impact the Group’s results of operations.

• The VAT exemption applicable to insurance and reinsurance transactions, including related services performed by insurance brokers and insurance agents has been the subject of a number of decisions of the CJEU which may be interpreted as having clarified a narrower scope of such exemption so as to apply to the supply of core insurance services and to brokerage services whereby prospective insurance clients are introduced to the insurer. In addition, the application of VAT exemption to insurance and reinsurance transactions is currently the subject of a review by the European Commission which may result in material amendments to the application of VAT to such services. Therefore, to the extent that FIID relies on such exemptions, in particular for the receipt or supply of such related or ancillary services, there is a risk that the application and scope of such exemptions may be amended and this could potentially give rise to material

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additional irrecoverable VAT costs in the structure. However, in circumstances where any entity in the structure is deemed to be carrying out activities which are subject to VAT (rather than exempt from VAT), such entity should be entitled to deduct any attributable input VAT.

• In addition, at present FIID may rely upon the existence of an Irish VAT group to result in no Irish VAT arising on supplies received by FIID from establishments outside Ireland of other Irish VAT group members. The Irish Revenue Commissioners have confirmed their interpretation that when an entity joins an Irish VAT group, the entire entity is deemed to be part of the Irish VAT group, which includes overseas establishments. It should be noted that a recent decision of the CJEU suggests that overseas establishments cannot form part of a VAT group and that VAT groups are perhaps limited in effect to supplies between establishments of VAT group members within the E.U. member state of such VAT group. Were Irish law to be amended and/or the Irish Revenue Commissioners to change their interpretation of the scope of an Irish VAT group, services provided by overseas establishments of any members of FIID’s Irish VAT group to other parties in the VAT group may give rise to additional irrecoverable Irish VAT costs in the structure where no VAT exemption applies to such services.

Any adverse adjustment under the proposed Council Directive to prevent the misuse of shell entities for tax purposes could adversely impact the Group’s tax liability.

• On December 22, 2021, the European Commission published a proposal for a Council Directive to prevent the misuse of shell entities for tax purposes (“ATAD III”). The new ATAD III proposals are aimed at legal entities which have limited substance and economic activity in their jurisdictions of residence. Where the rules apply, the proposal is that such entities should be denied the benefit of double taxation agreements entered into between E.U. member states as well as certain E.U. tax directives, including the Parent Subsidiary Directive and Interest and Royalty Directive.

• As currently drafted, the proposal contains exemptions for certain entities, including regulated insurance undertakings. There is no certainty that the proposal will be introduced in its current form. The proposal requires the unanimous approval of the E.U. Council before it is adopted. Until the proposal receives approval and a final directive is published, it is not possible to provide definitive guidance on the impact of the proposal on FIID’s Irish tax position (if any).

Risks Relating to Taxation—U.K. and Irish Tax Risks

Any adverse adjustment under the U.K. or Irish transfer pricing regimes, the anti-avoidance regime governing the transfer of corporate profits or the legislation governing the taxation of U.K. tax resident holding companies on the profits of their foreign subsidiaries could adversely impact the Group’s tax liability.

All intra-group services provided to or by FIHL or any of the U.K.-incorporated companies, including in particular the reinsurance arrangements between FIBL and FUL, FUL being a wholly owned subsidiary of the FIHL incorporated in England and Wales, are subject to the U.K. transfer pricing regime. In addition, the reinsurance arrangements between FIBL and FIID are subject to the Irish transfer pricing regime.

Consequently, if the reinsurance pursuant to these agreements (or any other intra-group services) is found not to be on arm’s-length terms and, as a result, a U.K. or Irish tax advantage is being obtained, an adjustment will be required to compute U.K. taxable profits for FUL, or to compute Irish taxable profits for FIID, as if the reinsurance or provision of marketing services were on arm’s-length terms.

Under section 1305A Corporation Tax Act 2009, where any payment between group companies is, in substance, a payment of all or a significant part of the profits of the business of the payer company, and the main purpose or one of the main purposes is to secure a tax advantage for any person, the payer’s profits are calculated for U.K. corporation tax purposes as if the profit transfer had not occurred. According to the Technical Note published by HMRC on March 19, 2014, where a company has entered into reinsurance arrangements within a

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group (for example quota share reinsurance) as part of ordinary commercial arrangements, this would not normally fall within the scope of this measure. This includes cases where the profitability of the ceding company is a factor taken into account in arriving at the premium to be paid.

DPT may apply in circumstances where (i) there is a transaction or series of transactions between a U.K. company and another related company, (ii) as a result of the transaction(s) there is a material reduction in the U.K. corporation tax liability of the U.K. company and (iii) it was reasonable to assume at the time of the transaction(s) that the financial benefits of the tax reduction would not be outweighed by the non-tax benefits.

Any transfer pricing adjustment, or the denial (in whole or in part) on any other basis, of a U.K. tax deduction for premiums paid pursuant to a reinsurance contract between companies in the Group, or the application of the DPT to the same, could adversely impact the Group’s U.K. corporation tax liability.

Under the U.K. CFC regime, the income profits of non-U.K. resident companies may in certain circumstances be attributed to controlling U.K.-resident shareholders for U.K. corporation tax purposes. The directors of each of the FIHL’S non-U.K. incorporated subsidiaries intend to operate those subsidiaries in such a manner that its profits are not taxed on FIHL under the CFC regime. Any change in the way in which each of the non-U.K. subsidiaries FIBL operates or any change in the CFC regime, resulting in an attribution of any of their income profits to FIHL for U.K. corporation tax purposes, could materially adversely affect the Group’s financial condition.

The financial results of the Group’s operations may be affected by measures taken in response to the OECD/G20 Two-Pillar Solution to address the tax challenges arising from the digitalization of the economy.

On October 5, 2015, the OECD released the final reports under its action plan on Base Erosion and Profit Shifting (“BEPS,” the action plan being the “BEPS Action Plan”). The actions contained in the BEPS Action Plan include a number of areas that could impact the Group, such as updated transfer pricing guidance and a broadened definition of “permanent establishment,” (both of which, to a certain extent, have been anticipated in the U.K. by the introduction of DPT), and new restrictions on interest deductions.

On October 8, 2021 the OECD/G20 Inclusive Framework on BEPS (the “IF”) issued a statement on the agreement of a two-pillar solution to address the tax challenges arising from the digitalization of the economy. This statement included the agreed components of the two pillars. Pillar One addresses the broader challenge of a digitalized economy and focuses on the allocation of group profits among taxing jurisdictions based on a market-based concept rather than historical “permanent establishment” concepts. Pillar One includes explicit exclusions for Regulated Financial Services (as defined therein), so is not expected to have a material impact on insurance and reinsurance groups. Pillar Two addresses the remaining BEPS risk of profit shifting to entities in low-tax jurisdictions by introducing a global minimum tax on large groups (groups with consolidated revenues in excess of €750 million), which would require large groups to calculate the effective tax rate of each group company operating in a relevant jurisdiction and, where a group company has an effective tax rate below 15%, pay an additional top-up tax. In December 2021, the OECD issued Pillar Two model rules for domestic implementation of the global minimum tax and shortly thereafter the European Commission proposed a Directive to implement the Pillar Two rules into E.U. law, which was unanimously agreed in December 2022 and will require E.U. member states to transpose the rules into their national laws by December 31, 2023, with certain measures initially coming into effect from January 1, 2024. The proposals, in particular in relation to Pillar Two, are broad in scope and FIHL is unable to determine at this time whether they would have a material adverse impact on its operations and results or those of any of its subsidiaries.

The U.K. and Ireland are currently legislating for the proposals set out in the IF statement with respect to the two-pillar solution and the final implemented legislation (and any further changes in U.K. or Irish tax law in response to the OECD’s initiatives described above) could materially adversely affect the Group’s liability to tax.

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Risks Relating to Taxation—Bermuda Tax Risks

FIHL and FIBL may become subject to taxes in Bermuda, which could negatively impact the Group’s results of operations.

FIHL and FIBL may become subject to taxes on capital gains and/or income in Bermuda after March 31, 2035, which may have a material adverse effect on the Group’s business, prospects, financial condition or results of operations. The Bermuda Minister of Finance (the “Minister”), under the Exempted Undertakings Tax Protection Act 1966 of Bermuda, as amended, has given FIHL and FIBL an assurance that if any legislation is enacted in Bermuda that would impose tax computed on profits or income, or computed on any capital asset, gain or appreciation, or any tax in the nature of estate duty or inheritance tax, then the imposition of any such tax will not be applicable to FIHL and/or FIBL and/or any of their respective operations, shares, debentures or other obligations until March 31, 2035 except insofar as such tax applies to persons ordinarily resident in Bermuda or is payable to FIHL or FIBL in respect of real property owned or leased by FIHL or FIBL in Bermuda. It cannot be certain that FIHL and FIBL will not be subject to any Bermuda tax after March 31, 2035.

The OECD’s review of harmful tax competition could adversely affect the Group’s tax status in Bermuda and elsewhere.

The OECD has published reports and launched a global dialogue among member and non-member countries on measures to limit harmful tax competition. These measures are largely directed at counteracting the effects of tax havens and preferential tax regimes around the world. Following a review in November 2021 by the OECD of Bermuda’s economic substance compliance, Bermuda was placed on the OECD’s “grey list.” Bermuda has already addressed the recommendations in practice and formalized these practices by April 2022. Following a formal review in October 2022, Bermuda was removed from the OECD’s grey list. However, the Group is not able to predict whether any changes will be made to this classification or whether any such changes will be subject to additional taxes.

The introduction of economic substance requirements in Bermuda required by the E.U. could adversely affect the Group.

During 2017, the E.U. Economic and Financial Affairs Council (the “ECOFIN”) released a list of non-cooperative jurisdictions for tax purposes. The stated aim of this list, and accompanying report, was to promote good governance worldwide in order to maximize efforts to prevent tax fraud and tax evasion. In an effort to remain off this list, Bermuda committed to address concerns relating to economic substance by December 31, 2018. In accordance with that commitment, Bermuda has enacted the Economic Substance Act 2018 (the “ES Act”). Pursuant to the ES Act, a registered entity other than an entity which is resident for tax purposes in certain jurisdictions outside Bermuda (“non-resident entity”) that carries on as a business any one or more of the “relevant activities” referred to in the ES Act must comply with economic substance requirements. The ES Act may require in scope Bermuda entities which are engaged in such “relevant activities” to be directed and managed in Bermuda, have an adequate level of qualified employees in Bermuda, incur an adequate level of annual expenditure in Bermuda, maintain physical offices and premises in Bermuda or perform core income-generating activities in Bermuda. The list of “relevant activities” includes carrying on any one or more of: banking, insurance, fund management, financing, leasing, headquarters, shipping, distribution and service center, intellectual property and holding entities. Any entity that must satisfy economic substance requirements but fails to do so could face automatic disclosure to competent authorities in the E.U. of the information filed by the entity with the Bermuda Registrar of Companies in connection with the economic substance requirements and may also face financial penalties, restriction or regulation of its business activities and/or may be struck off as a registered entity in Bermuda.

On July 19, 2019, the OECD’s Forum on Harmful Tax Practices formally reported its approval of Bermuda’s economic substance legislative framework. As the legislation is new and remains subject to further clarification and interpretation, it is not currently possible to predict the nature and effect of these requirements on the Group’s business. The new economic substance requirements may impact the manner in which the Group operates, which could adversely affect the Group’s business, prospects, financial condition or results of operations.

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Risks Relating to the Common Shares and this Offering

FIHL’s ability to pay dividends may be constrained by the Group’s structure, limitations on the payment of dividends which Bermuda law and regulations impose on the Group and the terms of our indebtedness.

FIHL is a holding company and, as such, has no substantial operations of its own. FIHL does not expect to have any significant operations or assets other than ownership of the shares of operating subsidiaries. Dividends and other permitted distributions and loans from operating subsidiaries are expected to be the sole source of funds to meet ongoing cash requirements, including payment of dividends to shareholders holding Series A Preference Securities, debt service payments and other expenses and to pay dividends, if any, to holders of the Common Shares. The Group’s operating subsidiaries are subject to significant regulatory restrictions limiting their ability to declare and pay dividends and make loans to other Group companies. FIHL’s ability to pay dividends on Common Shares is also dependent on the availability of distributable reserves. The inability of operating subsidiaries to pay dividends in an amount sufficient to enable FIHL to meet its cash requirements at the holding company level could have a material adverse effect on the Common Shares. As FIHL is subject to Group Supervision by the BMA, it is prohibited from declaring a dividend if it is in breach of its Group Enhanced Capital Requirement or the declaration or payment would cause such a breach. In addition, FIHL’s ability to pay dividends is subject to the restrictive covenants of our existing and outstanding indebtedness and may be limited by covenants of any future indebtedness we incur.

FIBL may be prohibited from declaring or paying dividends if it is in breach of its enhanced capital requirement, solvency margin or minimum liquidity ratio or if the declaration or payment of such dividend would cause such a breach. Where an insurer fails to meet its solvency margin or minimum liquidity ratio on the last day of any financial year, it is prohibited from declaring or paying any dividends during the next financial year without the approval of the BMA in its absolute discretion. Further, FIBL may be prohibited from declaring or paying in any financial year any dividend of more than 25% of its total statutory capital and surplus, unless it files with the BMA an affidavit stating that it will continue to meet its solvency margin or minimum liquidity ratio. FIBL will be required to obtain the BMA’s prior approval for a reduction by 15% or more of the total statutory capital as set forth in its previous year’s financial statements.

In addition, the Bermuda Companies Act 1981 (the “Companies Act”) limits the FIHL’s ability to pay dividends to shareholders. Under Bermuda law, when a company issues shares, the aggregate paid in par value of the issued shares comprises the company’s share capital account. When shares are issued at a premium the amount paid in excess of the par value must be allocated to and maintained in a capital account called the “share premium account.” The Companies Act requires shareholder approval prior to any reduction of the FIHL’s share capital or share premium account.

Under Bermuda law, FIHL may not declare or pay dividends, or make a distribution out of contributed surplus, if there are reasonable grounds for believing that (i) it is, or would after the payment be, unable to pay its liabilities as they become due; or (ii) the realizable value of its assets would thereby be less than its liabilities.

The PRA regulatory requirements impose no explicit restrictions on the Group’s U.K. subsidiaries’ ability to pay a dividend, but the Group would have to notify the PRA 28 days prior to any proposed dividend payment. Additionally, under the U.K. Companies Act 2006, dividends may only be distributed from profits available for distribution.

With respect to FIID, the Group would have to notify the CBI prior to any proposed dividend payment and FIID would only be permitted to proceed with the dividend if no communication is received from the CBI within 30 days of the notification. Additionally, under Irish company law, dividends may only be distributed from profits available for distribution, which consist of accumulated realized profits less accumulated realized losses.

Any difficulty or FIHL’s inability to receive dividends from its operating subsidiaries would have a material adverse effect on the Group’s business, prospects, financial condition or results of operations.

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No market currently exists for our Common Shares, and an active, liquid trading market for our Common Shares may not develop, which may cause our Common Shares to trade at a discount from the initial offering price and make it difficult to sell the Common Shares.

Prior to this offering, there has not been a public trading market for our Common Shares. The Group cannot predict the extent to which investor interest in FIHL will lead to the development of a trading market or how active and liquid that market may become. If an active and liquid trading market does not develop or continue, investors may have difficulty selling their Common Shares at an attractive price or at all. The initial public offering price per Common Share will be determined by negotiations between the Group and the underwriters, and may not be indicative of the price at which Common Shares will trade in the public market following the consummation of this offering. The market price of our Common Shares may decline below the initial offering price and investors may not be able to sell their Common Shares at or above the price they paid in this offering, or at all.

The price per Common Share may change significantly following this offering, and investors may not be able to resell their Common Shares at or above the price they paid or at all, and investors could lose all or part of their investment as a result.

The Group and the underwriters will negotiate to determine the initial public offering price. Investors may not be able to resell their Common Shares at or above the initial public offering price due to a number of factors such as those listed in this “Risk Factors” section and the following:

• occurrence of a large catastrophic loss;

• results of operations that vary from the expectations of securities analysts and investors;

• results of operations that vary from those of the Group’s competitors compared to market expectations;

• changes in expectations as to the Group’s future financial performance, including financial estimates and investment recommendations by securities analysts and investors;

• changes in market valuations of, or earnings and other announcements by, companies in the (re)insurance industry;

• declines in the market prices of stocks generally, particularly those in the (re)insurance industry;

• announcements by the Group or its competitors of significant contracts, new products or technologies, acquisitions, joint ventures, other strategic relationships or capital commitments;

• changes in general economic or market conditions or trends in the (re)insurance industry or the economy as a whole and, in particular, in the softening of rates;

• changes in business or regulatory conditions which adversely affect the (re)insurance industry, the Group or Fidelis MGU;

• future issuances, exchanges or sales, or expected issuances, exchanges or sales of the Common Shares or other securities of FIHL;

• investor perceptions, of or the investment opportunity associated with, the Common Shares relative to other investment alternatives;

• the market’s reaction to the Group’s outsourced underwriting arrangements with Fidelis MGU, which is a novel structure among the Group’s peers;

• the market’s reaction to the Group’s reduced disclosure and other requirements as a result of being treated as a “foreign private issuer”;

• the public’s response to press releases or other public announcements by the Group or third parties, including the Group’s filings with the SEC;

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• guidance, if any, that the Group provides to the public, any changes in this guidance or the Group’s failure to meet this guidance;

• the development and sustainability of an active trading market for our Common Shares; and

• other events or factors, including those resulting from informational technology system failures and disruptions, natural disasters, war, acts of terrorism or responses to these events.

Furthermore, the stock market has experienced and is likely to continue to experience extreme volatility and significant price and volume fluctuations that, in some cases, have been and may be unrelated or disproportionate to the operating performance of particular companies. These broad market and industry fluctuations may adversely affect the market price of our Common Shares, regardless of our actual operating performance. In addition, price volatility may be greater if the public float and trading volume of our Common Shares is low.

In the past, following periods of market volatility, shareholders have instituted securities class action litigation. If the Group were to become involved in securities litigation, it could have a substantial cost and divert resources and the attention of executive management from our business regardless of the outcome of such litigation.

If securities or industry analysts do not publish research or reports about the Group’s business or if they downgrade the Common Shares or the (re)insurance industry generally, or if there is any fluctuation in the Group’s ratings, the price of the Common Shares and trading volume could decline.

The trading market for our Common Shares will rely in part on the research and reports that industry or financial analysts publish about the Group and its business. The Group does not control these analysts. Furthermore, if one or more of the analysts who do cover the Group downgrade the Common Shares or the (re)insurance industry, or the stock of any of the Group’s competitors, or publish inaccurate or unfavorable research about the Group’s business, the price of Common Shares could decline. If one or more of these analysts stop covering the Group or fail to publish reports on it regularly, we could lose visibility in the market, which in turn could cause the price or trading volume of the Common Shares to decline.

Additionally, any fluctuation in the Group’s ratings may impact the Group’s ability to access debt markets in the future or increase the cost of future debt, which could have a material adverse effect on the Group’s operations and financial condition, which in return may adversely affect the trading price of the Common Shares.

As a foreign private issuer, there is less required publicly available information concerning FIHL than there would be if it were a U.S. public company.

FIHL is a “foreign private issuer,” as defined in the SEC’s rules and regulations and, consequently, it is not subject to all of the disclosure requirements applicable to public companies organized within the U.S. For example, FIHL is exempt from certain rules under the Exchange Act that regulate disclosure obligations and procedural requirements related to the solicitation of proxies, consents or authorizations applicable to a security registered under the Exchange Act, including the U.S. proxy rules under Section 14 of the Exchange Act. In addition, FIHL’s senior management and directors are exempt from the reporting and “short-swing” profit recovery provisions of Section 16 of the Exchange Act and related rules with respect to their purchases and sales of Common Shares or FIHL’s other securities. Moreover, FIHL is not required to file periodic reports and financial statements with the SEC as frequently or as promptly as U.S. public companies.

If FIHL or its existing shareholders sell additional Common Shares after this offering or are perceived by the public markets as intending to sell additional Common Shares, the market price of the Common Shares could decline.

The sale of substantial amounts of Common Shares in the public market, or the perception that such sales could occur, could harm the prevailing market price of the Common Shares. These sales, or the possibility that

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these sales may occur, also might make it more difficult for FIHL to sell Common Shares in the future at a time and at a price that it deems appropriate. Upon consummation of this offering, FIHL will have a total of 116,486,183 Common Shares outstanding. All of the Common Shares sold in this offering will be freely tradable without restriction or further registration under the Securities Act, by persons other than our “affiliates,” as that term is defined under Rule 144 of the Securities Act. Certain existing holders of our Common Shares and holders of Common Shares issued following the exercise of the outstanding warrants and RSUs have registration rights, pursuant to the Registration Rights Agreement (as defined below), subject to some conditions, to require us to file registration statements covering the sale of their shares or to include their shares in registration statements that we may file for ourselves or other shareholders in the future. In the event that we register the Common Shares for the holders of registration rights, they can be freely sold in the public market upon issuance. See “Shares Eligible for Future Sale” and “Material Contracts and Related Party Transactions—Registration Rights Agreement.”

The Selling Shareholders have agreed, subject to certain exceptions, not to dispose of or hedge any Common Shares for 180 days from the date of this prospectus, except with the underwriters’ prior written consent. See “Underwriting.” Upon the expiration of these lock-up agreements, all of such Common Shares will be eligible for resale in the public market, subject, in the case of Common Shares held by our affiliates, to volume, manner of sale and other limitations under Rule 144 and Rule 701. The market price of the Common Shares may decline when the restrictions on resale lapse. A decline in the price of our Common Shares might impede our ability to raise capital through the issuance of additional Common Shares or other equity securities. See “Description of Share Capital” and “Shares Eligible for Future Sale.”

Certain securities of FIHL rank senior to the Common Shares.

FIHL has previously issued certain securities that rank senior to the Common Shares. FIHL has in issue a number Series A Preference Securities as well as certain Notes (see “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Capital Management”). Both the Series A Preference Securities and the Notes rank senior to the Common Shares and have prior rights to interest payments, income and capital which may significantly affect FIHL’s capital attributable to the Common Shares and the likelihood that the Board will declare dividends payable on Common Shares. At March 31, 2023 FIHL had $58.4 million outstanding in liquidation preference of the Series A Preference Securities. See “Description of Share Capital.”

The Group may require additional capital in the future, which may not be available to it on satisfactory terms, if at all. Furthermore, the Group’s raising of additional capital could dilute the ownership interest of the holders of Common Shares and reduce the value of their investment. The Group may have to raise capital following significant insured losses, potentially resulting in capital being raised at valuations significantly below the original Common Share price.

The Group will require liquidity from sources of cash flows from operating, financing or investing activities to:

• pay claims;

• fund its operating expenses;

• to the extent declared, pay dividends (including the payment of dividends to the holders of the Series A Preference Securities);

• fund liquidity needs caused by investment losses;

• replace or improve capital in the event of a depletion of the Group’s capital as a result of significant reinsurance losses or adverse reserve developments;

• satisfy unfunded obligations in the event that it cannot obtain recoveries from its outwards reinsurance and retrocessional protection;

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• satisfy letters of credit or guarantee bond requirements that may be imposed by its clients or by its regulators;

• meet rating agency or regulatory capital requirements;

• respond to competitive pressures; and

• service its debt, including paying interest due on the Notes.

To the extent that the cash flow generated by the Group’s ongoing operations or investments is insufficient or unavailable, whether due to regulatory or contractual restrictions, underwriting or investment losses or otherwise, to cover its liquidity requirements, the Group may need to raise additional funds through financing. If the Group cannot obtain adequate capital or sources of credit on favorable terms, or at all, its business, results of operations or financial condition could be materially adversely affected.

Financial markets have experienced extreme volatility and disruption due in part to financial stresses affecting the liquidity of the banking system and the financial markets generally. These circumstances have reduced access to the public and private equity and debt markets at such times.

Future offerings of debt or equity securities which would rank senior to the Common Shares may adversely affect the market price of the Common Shares.

If, in the future, FIHL decides to issue debt or equity securities that rank senior to the Common Shares, it is likely that such securities will be governed by an indenture or other instrument containing covenants restricting the Group’s operating flexibility. Additionally, any convertible or exchangeable securities that FIHL may issue in the future may have rights, preferences and privileges more favorable than those of the Common Shares and may result in dilution to owners of the Common Shares. FIHL and, indirectly, its shareholders, will bear the cost of issuing and servicing such securities.

The Group takes a proactive approach to capital management based on opportunities presented and sought out. The Group may therefore seek to raise additional funds through opportunistic financings in order to take advantage of market conditions and opportunities to write more business. FIHL may raise such funds by issuing further securities including equity and debt, whether senior or subordinated in ranking.

Because the decision to issue debt or equity securities in any future offering will depend on market conditions and other factors beyond the Group’s control, the Group cannot predict or estimate the amount, timing or nature of such future offerings. Thus, holders of Common Shares will bear the risk of future offerings reducing the market price of the Common Shares and diluting the value of their holdings in FIHL.

Prior to the consummation of this offering, the current bye-laws of FIHL (the “Existing Bye-Laws”) will be amended and restated (the “Amended and Restated Bye-Laws”). The Amended and Restated Bye-Laws contain provisions that could impede an attempt to replace or remove the Board or delay or prevent the sale of FIHL, which could diminish the value of the Common Shares or prevent holders of Common Shares from receiving premium prices for their Common Shares in an unsolicited takeover.

The Amended and Restated Bye-Laws contain certain provisions that could delay or prevent changes in the Board or a change of control that a shareholder might consider favorable. These provisions may encourage companies interested in acquiring FIHL to negotiate in advance with the Board, since the Board has the authority to overrule the operation of several of the limitations. Even in the absence of a takeover attempt, these provisions may adversely affect the value of the Common Shares if they are viewed as discouraging takeover attempts in the future. For example, provisions in the Amended and Restated Bye-Laws that could delay or prevent a change in the Board or management or change in control include:

• the authorized number of directors may be increased by resolution adopted by the affirmative vote of a simple majority of the Board;

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• each of the Founders and MGU HoldCo has the right to nominate one individual to serve as a director on the Board and the Founders jointly, have the right to nominate one individual to serve as a director on the Board, subject to certain conditions;

• following the listing of the Common Shares on NYSE, the Board will be a classified board in which the directors of the class elected at each annual general meeting hold office for a term of three years, with the term of each class expiring at successive annual general meetings of shareholders. The classified board will be in place until the annual general meeting occurring in 2030, following which, all of the directors shall be of one class and shall serve for a term ending at the next following annual general meeting;

• shareholders may fill any vacancy on the Board at the meeting at which such director is removed, provided that in the event the vacancy to be filled is for a director nominated by a Founder or MGU HoldCo, then the relevant Founder or MGU HoldCo shall have the right to nominate a person to fill such vacancy and the Board shall promptly fill the vacancy with such successor nominee; it being understood that any such nominee shall serve the remainder of the term of the director whom such nominee replaces;

• each of the Founders and MGU HoldCo has a consent right before any amendments are made to the Amended and Restated Bye-Laws conferring special rights unto them so long as they each beneficially own a specified minimum percentage of our Common Shares or they have a designated director serving on the Board. These provisions relate to, among other things, the governance rights held by each of the Founders and MGU HoldCo and which are similarly reflected in the Amended and Restated Common Shareholders Agreement;

• advance notice of shareholders’ proposals is required in connection with annual general meetings; and

• a simple majority vote of shareholders is required to effect certain amendments to the Amended and Restated Bye-Laws.

Any such provision could prevent the shareholders from receiving the benefit from any premium to the market price of the Common Shares offered by a bidder in a takeover context. Moreover, jurisdictions in which the Group’s subsidiaries are domiciled have laws and regulations that require regulatory approval of a change in control of an insurer or an insurer’s holding company. Where such laws apply to the Group, there can be no effective change in our control unless the person seeking to acquire control has filed a statement with the regulators and has obtained prior approval for the proposed change from such regulators. The usual measure for a presumptive change in control pursuant to these laws is the acquisition of 10% or more of the voting power of the insurance company or its parent, although this presumption is rebuttable in some jurisdictions. Consequently, a person may not acquire 10% or more of the Common Shares without the prior approval of insurance regulators in the jurisdiction in which our subsidiaries are domiciled.

The Amended and Restated Common Shareholders Agreement will confer certain consent rights on MGU HoldCo and the Founders, which will allow them to exercise a certain amount of control over FIHL and limit other shareholders’ ability to influence the outcome of matters submitted to a shareholder vote.

Upon the completion of the Separation Transactions, MGU HoldCo became a 9.9% holder of our Common Shares. Under the terms of the Amended and Restated Common Shareholders Agreement, for so long as MGU HoldCo holds at least 4.9% of our Common Shares, once listed, the consent of MGU HoldCo is required to undertake a number of key corporate actions requiring shareholder approval, thereby having the ability to exercise substantial control over such actions, irrespective of how FIHL’s other shareholders may vote. Additionally, in relation to any proposed issuance of further Common Shares, MGU HoldCo has the benefit of an Allocation Right (as defined below; see “Material Contracts and Related Party Transactions—Consent Rights and Minority Protections”) effectively allowing it to purchase up to its pro rata portion of the Common Shares at a specific price and within a specific period, in accordance with the terms of the Amended and Restated Common Shareholders Agreement. There can be no assurance that courts and regulators will continue to permit consent, director appointment and other rights granted through a shareholders agreement. For the avoidance of doubt, if,

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following the consummation of this offering, MGU HoldCo sells any of its Common Shares, other than in connection with any stock conversions, buybacks, repurchases, redemptions, or other changes resulting from any stock split, combination or similar recapitalization, or its ownership of FIHL’s Common Shares otherwise falls below 4.9% as a consequence of a dilutive action taken by FIHL, MGU HoldCo will no longer be entitled to exercise its consent rights. See “Material Contracts and Related Party Transactions.” In addition, MGU HoldCo has a Board nomination right that may enable it to exercise a level of control through a director over corporate actions. See “Description of Share Capital—Certain Provisions of the Amended and Restated Bye-Laws—Number of Directors.”

For so long as the Founders, together with their Shareholder Affiliate Transferees, in the aggregate beneficially own at least 25% of the Common Shares, the Founders shall have the right, by unanimous decision by each Founder that beneficially owns at least 1% of the Common Shares, to restrict FIHL from taking the following actions, except to the extent such actions are required by applicable law: (i) adopt or propose to FIHL’s shareholders any amendment, modification or restatement of or supplement to FIHL’s organizational documents which have an adverse impact on the rights granted to the Founders, (ii) commence a voluntary case or proceeding under any applicable U.S. or foreign bankruptcy, insolvency, reorganization or similar law or make an assignment for the benefit of creditors, or admit in writing of its or their inability to pay its or their debts generally as they become due, or take any action in furtherance of any such action, (iii) change the size of the Board, (iv) engage in any transaction in which any person or group acquires more than 50% of the then outstanding Common Shares of FIHL or the power to elect a majority of the members of the Board or (v) terminate or hire the chief executive officer of FIHL or any successor or replacement serving in such role.

MGU HoldCo’s and the Founders’ consent rights may also adversely affect the trading price for the Common Shares to the extent investors perceive disadvantages in owning shares of a company with shareholders with the ability to exercise a degree of control and influence over such company. For example, MGU HoldCo’s and the Founders’ rights may delay, defer or prevent a change in control of FIHL or impede a merger, takeover or other business combination which may otherwise be favorable for the Group.

Any future exercise of the right of the holders of the Series A Preference Securities to convert, some or all of, their outstanding Series A Preference Securities in exchange for Common Shares in the event of a change of control may dilute the ownership interest of the holders of the Common Shares and reduce the value of their investment in FIHL.

The holders of the Series A Preference Securities have a right to convert some or all of their outstanding Series A Preference Securities in exchange for Common Shares in the event of a change of control of FIHL based on a certain conversion ratio. Any future issuance of Common Shares upon exercise of such right could dilute the ownership interests of the holders of the Common Shares. This may make it more difficult for a potential buyer to effectuate a change of control transaction where holders of Common Shares receive a premium on the Common Shares and may impact the price a potential buyer is willing to pay for FIHL.

U.S. persons who own Common Shares may have more difficulty in protecting their interests than U.S. persons who are shareholders of a U.S. corporation.

The Bermuda Companies Act, which applies to FIHL, differs in certain material respects from laws generally applicable to U.S. corporations and their shareholders. See “Comparison of Shareholder Rights” for a summary of certain significant provisions of the Bermuda Companies Act and the Amended and Restated Bye-Laws that differ in certain respects from provisions of Delaware corporate law.

The enforcement of civil liabilities against the Group may be difficult.

FIHL is a Bermuda company and some of its directors and officers are residents of various jurisdictions outside the U.S. All or a substantial portion of the Group’s assets and the assets of those persons may be located

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outside the U.S. As a result, it may be difficult for a shareholder to effect service of process within the U.S. upon those persons or to enforce in U.S. courts judgments obtained against those persons.

Puglisi & Associates is our agent for service of process with respect to actions based on offers and sales of securities made in the U.S. The Group has been advised by its special Bermuda legal counsel, Conyers Dill & Pearman Limited, that the U.S. and Bermuda do not currently have a treaty providing for reciprocal recognition and enforcement of judgments of U.S. courts in civil and commercial matters and that a final judgment for the payment of money rendered by a court in the U.S. based on civil liability, whether or not predicated solely upon the U.S. federal securities laws, would, therefore, not be automatically enforceable in Bermuda. The Group has been advised by Conyers Dill & Pearman Limited that a final and conclusive judgment obtained in a court in the U.S. under which a sum of money is payable as compensatory damages (i.e., not being a sum claimed by a revenue authority for taxes or other charges of a similar nature by a governmental authority, or in respect of a fine or penalty or multiple or punitive damages) may be the subject of an action on a debt in the Supreme Court of Bermuda under the common law doctrine of obligation.

Such an action should be successful upon proof that the sum of money is due and payable and without having to prove the facts supporting the underlying judgment, as long as: (i) the court which gave the judgment had proper jurisdiction over the parties to such judgment; (ii) such court did not contravene the rules of natural justice of Bermuda; (iii) such judgment was not obtained by fraud; (iv) the enforcement of the judgment would not be contrary to the public policy of Bermuda; (v) no new admissible evidence relevant to the action is submitted prior to the rendering of the judgment by the courts of Bermuda; and (vi) there is due compliance with the correct procedures under Bermuda law.

A Bermuda court may impose civil liability on FIHL or its directors or officers in a suit brought in the Supreme Court of Bermuda against it or such persons with respect to a violation of U.S. federal securities laws, provided that the facts surrounding such violation would constitute or give rise to a cause of action under Bermuda law.

Members of the Board will be permitted to participate in decisions in which they have interests that are different from those of the other shareholders.

Under Bermuda law, directors are not required to recuse themselves from voting on matters in which they have an interest. The directors may have interests that are different from, or in addition to, the interests of the shareholders. Provided the directors disclose their interests in a matter under consideration by the Board in accordance with Bermuda law and the Amended and Restated Bye-Laws, they will be entitled to participate in the deliberation on and vote in respect of that matter, unless the Board by resolution of a simple majority of the Board (which vote shall exclude the interested director) requires such director to abstain from any vote on the conflicted matter.

Shareholders will be limited in their rights relating to FIHL’s operations.

FIHL is managed exclusively by the Board. Shareholders do not make decisions with respect to the management, disposition or other realization of any investment, the day-to-day operations of FIHL and/or the Group, or any other decisions regarding the FIHL’s and/or the Group’s business and affairs, except for limited circumstances. Specifically, shareholders do not have an opportunity to evaluate for themselves the relevant economic, financial and other information regarding investments or underwriting by the Group. Shareholders should expect to rely solely on the ability of the Board with respect to the FIHL’s and the Group’s operations.

FIHL is permitted to adopt certain home country practices in relation to its corporate governance, which may afford investors less protection.

As a foreign private issuer, FIHL is permitted to adopt certain home country practices in relation to corporate governance matters that differ significantly from the NYSE corporate governance listing standards.

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These practices may afford less protection to shareholders than they would enjoy if FIHL complied fully with corporate governance listing standards.

As an issuer whose shares will be listed on NYSE, FIHL will be subject to the corporate governance listing standards of NYSE. However, NYSE rules permit a foreign private issuer like FIHL to follow the corporate governance practices of its home country. FIHL may elect not to comply with certain corporate governance requirements of NYSE.

Certain corporate governance practices in Bermuda, which is our home country, may differ significantly from the NYSE corporate governance listing standards. Currently, FIHL intends to comply with all NYSE corporate governance listing standards for a foreign private issuer. See “Management and Corporate Governance.” If, however, FIHL chose not to comply with certain NYSE corporate governance listing standards and instead rely on the Bermuda requirements, shareholders may be afforded less protection than they otherwise would have.

FIHL may lose its foreign private issuer status which would then require it to comply with the Exchange Act’s domestic reporting regime and cause it to incur additional legal, accounting and other expenses.

For so long as FIHL qualifies as a foreign private issuer, it is not required to comply with all of the periodic disclosure and current reporting requirements of the Exchange Act applicable to U.S. domestic issuers. In order to maintain its current status as a foreign private issuer, either (a) a majority of Common Shares must be either directly or indirectly owned of record by non-residents of the U.S. or (b)(i) a majority of FIHL’s executive officers or directors cannot be U.S. citizens or residents, (ii) more than 50% of FIHL’s assets must be located outside the U.S. and (iii) FIHL’s business must be administered principally outside the U.S.

If FIHL loses its status as a foreign private issuer, it would be required to comply with the Exchange Act reporting and other requirements applicable to U.S. domestic issuers, which are more detailed and extensive than the requirements for foreign private issuers. FIHL may also be required to make changes in its corporate governance practices in accordance with various SEC and NYSE rules. For example, the annual report on Form 10-K requires domestic issuers to disclose executive compensation information on an individual basis with specific disclosure regarding the domestic compensation philosophy, objectives, annual total compensation (base salary, bonus, and equity compensation) and potential payments in connection with change in control, retirement, death or disability, while the annual report on Form 20-F permits foreign private issuers to disclose compensation information on an aggregate basis. FIHL would also have to mandatorily comply with U.S. federal proxy requirements, and its officers, directors, and principal shareholders will become subject to the short-swing profit disclosure and recovery provisions of Section 16 of the Exchange Act.

The regulatory and compliance costs to the Group under U.S. securities laws if FIHL were required to comply with the reporting requirements applicable to a U.S. domestic issuer may be higher than the cost the Group would incur if FIHL remains a foreign private issuer. As a result, we expect that a loss of foreign private issuer status would increase the Group’s legal and financial compliance costs and is likely to make some activities highly time consuming and costly.

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USE OF PROCEEDS

We estimate that the net proceeds to us from the sale of Common Shares in this offering will be approximately $87.7 million, based upon the assumed initial public offering price of $17.50 per Common Share, which is the midpoint of the estimated offering price range set forth on the cover page of this prospectus, and after deducting the estimated underwriting discounts and estimated offering expenses payable by us. An increase in the offering price above the midpoint of the estimated offering price range set forth on the cover page of this prospectus will result in us selling fewer Common Shares such that our gross proceeds will not exceed $100.0 million. We will not receive any of the proceeds from the sale of our Common Shares in this offering by the Selling Shareholders.

A $1.00 decrease in the assumed initial public offering price of $17.50 per Common Share would decrease the net proceeds that we receive from this offering by approximately $5.4 million, assuming that the number of Common Shares offered by us, as set forth on the cover page of this prospectus, remains the same and after deducting the estimated underwriting discounts and estimated offering expenses payable by us. An increase in the offering price above the midpoint of the estimated offering price range set forth on the cover page of this prospectus will result in us selling fewer Common Shares such that our gross proceeds will not exceed $100.0 million.

We intend to use the net proceeds to us from this offering to make capital contributions to our insurance operating subsidiaries, which, together with other sources of liquidity, should enable us to take advantage of the ongoing rate hardening in the key markets in which we participate by writing more business under our planned strategy (as discussed in more detail in “Business—Our Strategy” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Liquidity and Capital Resources”).

This expected use of net proceeds from this offering represents our intentions based on our current plans and business conditions, which could change in the future as our plans and business conditions evolve. As a result, our management will have broad discretion over the uses of the net proceeds from this offering and investors will be relying on the judgment of our management regarding the application of the net proceeds from this offering.

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DIVIDEND POLICY

The declaration, amount and payment of any dividends on our Common Shares will be at the sole discretion of the Board, which may take into account general and economic conditions, our financial condition and results of operations, our available cash and current and anticipated cash needs, capital requirements, contractual, legal, tax and regulatory restrictions and implications on the payment of dividends by us to our shareholders or by our subsidiaries to us, including restrictions under any of our then outstanding indebtedness, and such other factors as the Board may deem relevant. If we elect to pay dividends in the future, we may reduce or discontinue entirely the payment of such dividends at any time. At the Board’s discretion, we declare and pay a dividend quarterly on the Series A Preference Securities, which rank senior to and have priority over the Common Shares. The Board approved a dividend of $225.0 per Series A Preference Security with a record date of February 15, 2023, paid on March 15, 2023. The Board also approved a dividend of $225.0 per Series A Preference Security with a record date of May 15, 2023, to be paid on June 15, 2023. For a more detailed description of the Series A Preference Securities see “Material Contracts and Related Party Transactions—Preference Securityholders Agreement.”

FIHL is a holding company and, as such, has no substantial operations of its own. FIHL does not expect to have any significant operations or assets other than ownership of the shares of its insurance operating subsidiaries. As a result, we will not be able to pay any dividends unless Current Fidelis’ insurance operating subsidiaries make distributions in an amount sufficient to cover the dividend that may be declared by FIHL. Moreover, Current Fidelis’ operating subsidiaries are subject to significant regulatory restrictions limiting their ability to declare and pay dividends to other Group companies. FIHL’s ability to pay dividends on Common Shares will also be dependent on the availability of distributable reserves.

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CAPITALIZATION

The following table sets forth our consolidated capitalization at March 31, 2023:

• on a historical basis for Current Fidelis; and

• on an as-adjusted basis to give effect to our issuance and sale of Common Shares in this offering at an assumed initial public offering price of $17.50 per Common Share, the midpoint of the price range set forth on the cover page of this prospectus, after deducting the estimated underwriting discounts and estimated offering expenses payable by us. We will not receive any proceeds from the sale of our Common Shares by the Selling Shareholders.

You should read the following table in conjunction with the sections entitled “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and “Summary Financial and Operating Data—Summary Statement of Operations Data,” as well as the audited consolidated financial statements and accompanying notes included elsewhere in this prospectus.

The as-adjusted information set forth in the table below is illustrative only and will be adjusted based on the terms of this offering determined at pricing.

($ in millions)	At March 31, 2023			As-adjusted following consummation of this offering(1)
Long-term debt obligations:
4.875% Senior Notes due 2030	$	324.5		$	324.50
6.625% Fixed Rate Reset Junior Subordinated Notes due 2041		123.2			123.2
Total long-term debt obligations		447.7			447.7
Preference securities		58.4			58.4
Shareholders’ equity:
Common Shares of par value $0.01 per share: 110,771,897 issued and outstanding, actual; and 116,486,183 issued and outstanding, as-adjusted following consummation of this offering.		1.1			1.2
Additional paid-in capital		1,943.5			2,031.2
Accumulated other comprehensive loss		(76.8	)	$	(76.8	)
Retained earnings		36.7			36.7
Total shareholders’ equity	$	1,904.5		$	1,992.3
Total capitalization	$	2,410.6		$	2,498.4

(1) The “As-adjusted following consummation of this offering” column reflects the changes in the capital of FIHL on an as-adjusted basis following the consummation of this offering. A $1.00 decrease in the assumed initial public offering price of $17.50 per Common Share would decrease the net proceeds that we receive from this offering by approximately $5.4 million, assuming that the number of Common Shares offered by us, as set forth on the cover page of this prospectus, remains the same and after deducting the estimated underwriting discounts and estimated offering expenses payable by us. An increase in the offering price above the midpoint of the estimated offering price range set forth on the cover page of this prospectus will result in us selling fewer Common Shares such that our gross proceeds will not exceed $100.0 million.

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DILUTION

If you invest in our Common Shares in this offering, your interest will be immediately diluted to the extent of the difference between the initial public offering price per Common Share in this offering and the book value per Common Share after this offering. At March 31, 2023, we had a historical net book value of $1,904.5 million, or $17.19 per Common Share. Our net book value represents total assets less total liabilities, all divided by the number of Common Shares outstanding on such date.

After giving further effect to the sale of 5,714,286 Common Shares in this offering at an assumed initial public offering price of $17.50 per Common Share, the midpoint of the price range set forth on the cover page of this prospectus and after deducting the estimated underwriting discounts and estimated offering expenses payable by us, our as adjusted net book value at March 31, 2023 would have been $1,992.3 million, or $17.10 per Common Share. This represents an immediate decrease in book value of $0.09 per Common Share to existing shareholders and an immediate dilution in book value of $0.40 per Common Share to new investors purchasing Common Shares in this offering. Dilution per Common Share to new investors is determined by subtracting as adjusted book value per Common Share after this offering from the initial public offering price per Common Share paid by new investors. The following table illustrates this per Common Share dilution:

Assumed initial public offering price per Common Share				$	17.50
Historical book value per Common Share at March 31, 2023	$	17.19
Decrease in book value per Common Share attributable to this offering		(0.09	)
As adjusted book value per Common Share after this offering					17.10
Dilution in book value per Common Share to new investors in this offering				$	0.40

A $1.00 decrease in the assumed initial public offering price of $17.50 per Common Share, the midpoint of the price range set forth on the cover page of this prospectus, would decrease, our as adjusted book value per Common Share after this offering by $0.05, and would decrease dilution per Common Share to new investors in this offering by $0.95, in each case assuming that the number of Common Shares offered by us, as set forth on the cover page of this prospectus, remains the same and after deducting the estimated underwriting discounts and estimated offering expenses payable by us. An increase in the offering price above the midpoint of the estimated offering price range set forth on the cover page of this prospectus will result in us selling fewer Common Shares such that our gross proceeds will not exceed $100.0 million.

The following table summarizes, on an as adjusted basis at March 31, 2023, the differences between the number of Common Shares purchased from us, the total consideration paid and the average price per Common Share paid by existing shareholders and to be paid by the new investors purchasing Common Shares in this offering, at the assumed initial public offering price of $17.50 per Common Share, the midpoint of the price range set forth on the cover page of this prospectus, before deducting the estimated underwriting discounts and estimated offering expenses payable by us:

	Common Shares purchased					Total consideration
	Number		Percent			Amount ($ in millions)		Percent			Average price per share
Existing investors		110,771,897		95.1	%	$	1,944.6		95.1	%	$	17.55
New investors in this offering		5,714,286		4.9			100.0		4.9		$	17.50
Total		116,486,183		100	%	$	2,044.6		100.0	%

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Sales by the Selling Shareholders in this offering will reduce the number of Common Shares held by existing shareholders to 99,343,383, or approximately 85.3% of the total Common Shares outstanding after this offering, and will increase the number of Common Shares held by new investors to 17,142,799, or 14.7% of the total Common Shares outstanding after this offering.

The table above assumes no exercise of the underwriters’ option to purchase additional Common Shares from the Selling Shareholders in this offering. If the underwriters’ option to purchase additional Common Shares from the Selling Shareholders is exercised in full, the number of Common Shares held by existing shareholders would be reduced to 83.1% of the total number of Common Shares outstanding after this offering, and the number of Common Shares held by new investors purchasing Common Shares in this offering would be increased to 16.9% of the total number of Common Shares outstanding after this offering.

The number of Common Shares that will be outstanding after this offering is based on 110,771,897 Common Shares issued and outstanding immediately prior to the closing of this offering, and excludes 4,615,500 Common Shares reserved for issuance under our 2023 Long-Term Incentive Plan.

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CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS

This prospectus contains forward-looking statements that are intended to enhance the reader’s ability to assess our future financial and business performance. These statements are based on the beliefs and assumptions of our management, and are subject to known and unknown risks and uncertainties. Generally, statements that are not about historical facts, including statements concerning our possible or assumed future actions or results of operations, are forward-looking statements. Forward-looking statements include, but are not limited to, statements that represent our beliefs, expectations or estimates concerning future operations, strategies, financial results or performance, financings, investments, acquisitions, expenditures or other developments and anticipated trends and competition in the markets in which we operate. Forward-looking statements can also be identified by the use of forward-looking terminology such as “may,” “believes,” “intends,” “anticipates,” “plans,” “estimates,” “targets,” “potential,” “will,” “can have,” “likely,” “continue,” “expects,” “should,” “could” or similar expressions.

Forward-looking statements are not guarantees of performance and we caution prospective investors not to rely on them. We qualify all of our forward-looking statements by these cautionary statements, because these forward-looking statements are based on estimates and assumptions that are subject to significant business, economic and competitive uncertainties, many of which are beyond our control or are subject to change. Actual results or other outcomes could differ materially from those expressed or implied in our forward-looking statements, as a result of several factors, including the following:

• changes to our strategic relationship with MGU HoldCo or the termination by MGU HoldCo or any of its subsidiaries of any of the Framework Agreement, the Delegated Underwriting Authority Agreements or the Inter-Group Services Agreement;

• our dependence on the Delegated Underwriting Authority Agreements for our underwriting and claims handling operations;

• our ability to manage risks associated with macroeconomic conditions resulting from the global COVID-19 pandemic or any other public health crisis, current or anticipated military conflict, including the ongoing Ukraine Conflict, terrorism, sanctions, rising energy prices, inflation and interest rates and other geopolitical events globally;

• our ability to successfully implement our strategy following the Separation Transactions;

• our limited operating history;

• fluctuations in the results of our operations;

• market reaction amongst clients, brokers and reinsurers and other trading partners to the Separation Transactions and this offering;

• our ability to compete successfully with more established competitors and risks relating to consolidation in the reinsurance and insurance industries;

• our losses exceeding our reserves;

• downgrades, potential downgrades or other negative actions by rating agencies;

• our dependence on key executives and inability to attract qualified personnel and in particular in very competitive hiring conditions, or the potential loss of Bermudian personnel as a result of Bermuda employment restrictions;

• our dependence on letter of credit facilities that may not be available on commercially acceptable terms;

• our potential inability to pay dividends or distributions;

• our potential need for additional capital in the future and the potential unavailability of such capital to us on favorable terms or at all;

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• our dependence on clients’ evaluations of risks associated with such clients’ insurance underwriting;

• the suspension or revocation of our subsidiaries’ insurance licenses;

• FIHL potentially being deemed an investment company under U.S. federal securities law;

• the potential characterization of us and/or any of our subsidiaries as a passive foreign investment company, or PFIC;

• risks associated with our investment strategy being greater than those faced by competitors;

• changes in the regulatory environment and the potential for greater regulatory scrutiny of the Group going forward as a result of the outsourcing arrangements;

• a cyclical downturn of the (re)insurance industry;

• the impact of inflation or deflation in relevant economies in which we operate;

• our ability to evaluate and measure our business, prospects and performance metrics;

• the failure of our risk management policies and procedures to be adequate to identify, monitor and manage risks, which may leave us exposed to unidentified or unanticipated risks;

• operational failures, including the operational risk associated with the outsourcing to Fidelis MGU, failure of information systems or failure to protect the confidentiality of customer information, including by service providers, or losses due to defaults, errors or omissions by third parties and affiliates;

• FIHL’s status as a foreign private issuer means that it will not be subject to U.S. proxy rules and will be subject to Exchange Act reporting obligations that, to some extent, are more lenient and less frequent than those of a U.S. domestic public company;

• risks relating to our ability to identify and execute opportunities for growth or our ability to complete transactions as planned or realize the anticipated benefits of our acquisitions or other investments;

• our ability to maintain effective internal controls and changes in U.S. GAAP;

• our ability to maintain effective internal controls and procedures under the applicable corporate governance requirements of the Sarbanes-Oxley Act of 2002, the rules adopted by the SEC and the NYSE corporate governance rules and listing standards;

• our ability to maintain the listing of our Common Shares on NYSE or another national securities exchange;

• our potentially becoming subject to U.S. federal income taxation;

• our potentially becoming subject to U.S. withholding and information reporting requirements under the U.S. Foreign Account Tax Compliance Act, or FATCA, provisions; and

• the other risks identified in this prospectus, including, without limitation, those under the sections titled “Risk Factors,” “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and “Business.”

Consequently, such forward-looking statements should be regarded solely as our current plans, estimates or belief as of the date of this prospectus. We do not intend, and do not undertake, any obligation to update any forward-looking statements to reflect future events or circumstances after the date of this prospectus. Given such limitations, prospective investors should not rely on these forward-looking statements in deciding whether to invest in our Common Shares.

Prospective investors should review carefully the section captioned “Risk Factors” in this prospectus for a more complete discussion of risks and uncertainties relating to an investment in our Common Shares.

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THE SEPARATION TRANSACTIONS

References to “Previous Fidelis” refer to FIHL and its consolidated subsidiaries prior to the consummation of the Separation Transactions and this offering. References to “Current Fidelis” refer to FIHL and its consolidated subsidiaries following the consummation of the Separation Transactions. Unless otherwise indicated, or the context otherwise requires, references herein to “Fidelis,” “Group,” “we,” “our,” “us,” and other similar references refer (i) prior to the consummation of the Separation Transactions and this offering to Previous Fidelis and (ii) following the consummation of the Separation Transactions to Current Fidelis.

Overview

On July 23, 2022, FIHL and MGU HoldCo, among others, entered into a Cooperation Agreement (as defined herein) agreeing to cooperate regarding certain matters related to this offering and the furtherance of the Separation Transactions. See “Material Contracts and Related Party Transactions—Cooperation Agreement.” On January 3, 2023, the Separation Transactions were completed and two distinct holding companies and businesses were created: FIHL and MGU HoldCo.

FIHL is the parent holding company for Current Fidelis. It is the issuer of the Common Shares sold by the holders of Common Shares in this offering and it owns all of the operating insurance carrier subsidiaries of Current Fidelis (i.e., FIBL, FUL and FIID).

MGU HoldCo is the parent holding company of Fidelis MGU that carries on the origination and underwriting activities on behalf of Current Fidelis. MGU HoldCo’s principal operating subsidiaries are Bermuda MGU, Pine Walk Capital and Pine Walk Europe. The underwriting activities of each of the licensed insurance carriers of Current Fidelis (FIBL, FUL and FIID) are outsourced to the corresponding operating subsidiaries of Fidelis MGU on a jurisdictional basis (Bermuda MGU, Pine Walk Capital and Pine Walk Europe, respectively). Each of the operating subsidiaries of Fidelis MGU has delegated underwriting authority to source and bind contracts for and on behalf of each of FIBL, FUL and FIID, respectively. See “Material Contracts and Related Party Transactions—Framework Agreement.” MGU HoldCo and its subsidiaries will not be consolidated with FIHL and its subsidiaries. The Fidelis MGU’s principal investors include the Alfa Entities, SPFM Holdings, LLC and Capital Z and entities affiliated with Capital Z (each, as defined below), Further Global Capital, Barings LLC, Oak Hill Advisors and Blackstone.

Current Fidelis also has a U.K. service company, FIHL (UK) Services, with a branch in Ireland. MGU HoldCo owns 100% of the outstanding shares of FML, a U.K. service company (which also has a branch in Ireland).

The Separation Transactions involved a number of steps to reorganize the structure of Previous Fidelis and to establish Fidelis MGU - a new, stand-alone platform, comprising a series of jurisdiction-specific managing general underwriting entities (i.e., Bermuda MGU, Pine Walk Capital and Pine Walk Europe, as noted above), each of which entered into a Delegated Underwriting Authority Agreement with the relevant operating insurance carrier subsidiary of Current Fidelis for each applicable jurisdiction (i.e., the United Kingdom, Ireland/the EEA and Bermuda). See “Business—Strategic Relationship with the MGU” for further detail. In order to effect the Separation Transactions, FIHL transferred its shares in FML, Fidelis U.S. Holdings, LLC (“Fidelis U.S.”), Pine Walk Capital and Radius Specialty Limited to MGU HoldCo. As part of the new Fidelis MGU, certain new entities or branches of transferring Group companies were established in the relevant jurisdictions, supported by the necessary personnel, and were authorized to operate as managing general underwriters under the applicable regulatory rules.

In connection with the Separation Transactions, certain capabilities of Previous Fidelis, including underwriting and non-underwriting business support services, were transferred to Fidelis MGU. The underwriting relationship between Current Fidelis and Fidelis MGU is governed primarily by the Framework Agreement, which was entered into by FIHL and MGU HoldCo. There are also a series of jurisdiction-specific Delegated Underwriting Authority Agreements, which were entered into between each of Current Fidelis’

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operating insurance carrier subsidiaries and the applicable subsidiaries of Fidelis MGU. See “Material Contracts and Related Party Transactions—Framework Agreement.”

FIHL and MGU HoldCo have also entered into the Inter-Group Services Agreement in connection with applicable non-underwriting business support services to be provided by Fidelis MGU to either: (i) FIHL and FIHL (UK) Services; or (ii) upon mutual agreement between FIHL and Fidelis MGU, any entity within Current Fidelis. The covered services include accounting services, other finance and reporting services and IT infrastructure maintenance and system development services. Pursuant to the Inter-Group Services Agreement, MGU HoldCo must place relevant source codes for critical proprietary systems (including Prequel, Jarvis, and FireAnt) in an escrow arrangement.

The Framework Agreement, the Delegated Underwriting Authority Agreements and the Inter-Group Services Agreement are of sufficiently critical importance to the business of Current Fidelis that the arrangements are treated as “material outsourcing” under the PRA rules, the BMA outsourcing guidance and by the CBI under the Solvency II rules for outsourcing critical or important functions or activities. As a result, these agreements were and are subject to certain regulatory notifications and requirements. See “Certain Regulatory Considerations” for further detail.

Following the consummation of the Separation Transactions, MGU HoldCo became a shareholder of FIHL, holding 9.9% of our Common Shares. See “Material Contracts and Related Party Transactions.”

Current Fidelis Structure

The diagram below provides a simplified overview of the principal organizational structure of Current Fidelis, which, other than the percentage ownership changes noted at note (1) below, will remain unchanged following the consummation of this offering. Current Fidelis primarily consists of FIHL and its principal operating insurance subsidiaries, FIBL, FUL and FIID, together with its service company, FIHL (UK) Services.

Current Fidelis Structure

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(1) See “Principal and Selling Shareholders” for detail of the percentage ownership prior to this offering, as well as the percentage ownership of FIHL following the consummation of this offering (including in the event of a full option exercise) by each of MGU HoldCo, the Founders, other institutional investors, management and other existing shareholders.

(2) FUL is a limited liability company incorporated in England and Wales, authorized by the PRA and supervised by the FCA and the PRA as an insurer.

(3) FIBL is a limited liability company incorporated in Bermuda, authorized and supervised by the BMA as an insurer.

(4) FIHL (UK) Services is a limited liability company incorporated in England and Wales and is the service company of Current Fidelis. FIHL (UK) Services also has a branch in Ireland.

(5) FEHL is a limited liability company incorporated in England and Wales.

(6) FIID is a designated activity company incorporated in Ireland, is authorized and supervised by the CBI as an insurer.

Fidelis MGU

The diagram below provides a simplified overview of Fidelis MGU’s principal organizational structure. Fidelis MGU primarily consists of MGU HoldCo and the platform’s managing general underwriting entities, Pine Walk Capital in the U.K., Pine Walk Europe, a Belgian company operating via its Ireland and U.K. branches, and Bermuda MGU, together with FML as the service company of Fidelis MGU.

Fidelis MGU Group Structure

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UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

The following unaudited pro forma condensed combined financial information gives effect to the Separation Transactions and the related transaction accounting and autonomous entity adjustments. The unaudited pro forma condensed combined financial information should be read in conjunction with our audited consolidated financial statements and the accompanying notes at and for the year ended December 31, 2022 included elsewhere in this prospectus.

The unaudited pro forma condensed combined statement of income for the year ended December 31, 2022 has been prepared to give effect to the Separation Transactions as if these transactions had occurred on January 1, 2022.

The unaudited pro forma condensed combined balance sheet at December 31, 2022 has been prepared to give effect to the Separation Transactions as if these transactions had occurred on December 31, 2022.

Basis of Pro Forma Presentation

The following unaudited pro forma condensed combined financial information and related notes (the “Pro Forma Financial Information”) has been prepared in accordance with Article 11 of Regulation S-X, as amended by the final rule, Release No. 33-10786, and has been derived from the historical consolidated financial statements of the Group that were prepared in accordance with U.S. GAAP, adjusted to reflect expected effects of the Separation Transactions.

The unaudited pro forma condensed combined financial information is presented, to give effect to adjustments which are considered necessary to enable an understanding of the entities and their operations after the Separation Transactions, including:

Transaction Accounting Adjustments which include:

• the impact of the Separation Transactions in respect of the distribution of Fidelis MGU to the FIHL shareholders, resulting in the deconsolidation and consequent elimination of the net assets of Fidelis MGU and its subsidiaries, and

• other adjustments including the acceleration of vesting of restricted stock units, the exercise of warrants, and the related tax impact of these adjustments.

Autonomous Entity Adjustments which reflect the impact of certain agreements as part of the Separation Transactions. These include:

• the inclusion of commissions and expenses that will be paid to Fidelis MGU for sourcing and managing the insurance business under the Framework Agreement,

• the impact of additional costs for staff and services that will be required by the Group to undertake certain functions as a standalone entity,

• the removal of costs in respect of employees and related overheads that have transferred to Fidelis MGU, and

• the inclusion of costs reflecting the charges set out in the Inter-Group Services Agreement for the services to be provided by Fidelis MGU, and

• the inclusion of commissions and expenses that will be paid to Fidelis MGU for sourcing and managing the insurance business under the Framework Agreement.

See “Material Contracts and Related Party Transactions” for further information on the charges expected to be levied on the Group in accordance with the Framework Agreement and Inter-Group Services Agreement.

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The unaudited pro forma condensed combined financial information is provided for illustrative and informational purposes only. The pro forma adjustments are based upon available information and certain assumptions that management believes are reasonable, that reflect the impact of the Separation Transactions as if they had been consummated at a prior date. The unaudited pro forma condensed combined financial information is not necessarily indicative of the financial results that would have been obtained had the Separation Transactions occurred on and at the dates referenced above and should not be viewed as indicative of the results of operations or financial position of the Group in future periods.

Fidelis Insurance Holdings Limited

Unaudited Pro Forma Condensed Combined Balance Sheet At December 31, 2022

(Expressed in millions of U.S. dollars)

	FIHL at December 31, 2022		Transaction Accounting Adjustments			Autonomous Entity Adjustments		Pro Forma Balance Sheet
Assets
Fixed maturity securities, available-for-sale at fair value	$	2,050.9	$	—		$	—	$	2,050.9
Short-term investments, available-for-sale at fair value		257.0							257.0
Other investments, at fair value		117.1							117.1
Total investments	$	2,425.0	$	—		$	—	$	2,425.0
Cash and cash equivalents		1,222.0		(231.5	) (a) (b)				990.5
Restricted cash and cash equivalents		185.9							185.9
Derivative assets, at fair value		6.3							6.3
Accrued investment income		10.9							10.9
Investments pending settlement		2.0							2.0
Premiums and other receivables		1,862.7		9.3	(a)				1,872.0
Deferred reinsurance premiums		823.7							823.7
Reinsurance balances recoverable on paid losses		159.4							159.4
Reinsurance balances recoverable on reserves for losses and loss adjustment expenses		976.1							976.1
Deferred policy acquisition costs		515.8		0.2	(a)				516.0
Deferred tax asset		58.5		(7.3	) (a)				51.2
Operating right of use assets		26.8							26.8
Other assets		37.4		(11.8	) (a)				25.6
Total Assets	$	8,312.5	$	(241.1	)	$	—	$	8,071.4
Total shareholders’ equity attributable to common shareholders
Liabilities
Reserves for losses and loss adjustment expenses		2,045.2							2,045.2
Unearned premiums		2,618.6							2,618.6
Reinsurance balances payable		1,057.0							1,057.0
Long term debt		447.5							447.5
Preference securities		58.4							58.4
Other liabilities		70.2		(52.4	) (a)				17.8
Operating lease liabilities		28.5							28.5
Total Liabilities	$	6,325.4	$	(52.4	)	$	—	$	6,273.0

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	FIHL at December 31, 2022			Transaction Accounting Adjustments			Autonomous Entity Adjustments		Pro Forma Balance Sheet
Shareholders’ equity
Ordinary shares		1.9								1.9
Additional paid-in capital		2,075.2			(132.4	) (c)				1,942.8
Accumulated other comprehensive loss		(100.8	)		1.1	(d)				(99.7	)
Accumulated deficit		0.5			(47.1	) (e)				(46.6	)
Total shareholders’ equity attributable to common shareholders	$	1,976.8		$	(178.4	)	$	—	$	1,798.4
Non-controlling interests		10.3			(10.3	) (f)				—
Total shareholders’ equity including non-controlling interests		1,987.1		$	(188.7	)	$	—	$	1,798.4
Total liabilities and shareholders’ equity	$	8,312.5		$	(241.1	)	$	—	$	8,071.4

Explanatory notes (a) to (f) are contained within note 4 “Transaction Accounting Adjustments” of this unaudited pro forma condensed combined financial information.

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Fidelis Insurance Holdings Limited

Unaudited Pro Forma Condensed Combined Statement of Operations for the year ended December 31, 2022

(Expressed in millions of U.S. dollars except for per share data)

	FIHL 2022			Transaction Accounting Adjustments			Autonomous Entity Adjustments			Pro Forma Statement of Operations
Revenues
Gross premiums written	$	3,000.1		$			$	(10.3	) (i)	$	2,989.8
Reinsurance premiums ceded		(1,137.5	)					(5.4	) (m)		(1,142.9	)
Net premiums written		1,862.6			—			(15.7	)		1,846.9
Change in net unearned premiums		(357.9	)								(357.9	)
Net premiums earned		1,504.7			—			(15.7	)		1,489.0
Net investment losses		(33.7	)								(33.7	)
Net investment income		40.7						(0.1	) (i)		40.6
Net foreign exchange gains		6.8						(2.7	) (i)		4.1
Net gain on distribution of Fidelis MGU		—			1,638.1	(g)					1,638.1
Other income		1.9						(1.6	) (i)		0.3
Total revenues	$	1,520.4		$	1,638.1		$	(20.1	)	$	3,138.4
Expenses
Losses and loss adjustment expenses		830.2									830.2
Policy acquisition expenses (includes Fidelis MGU commissions of $119.5)		447.7						81.7	(j)		529.4
General and administrative expenses		106.4						(35.3	) (k)		71.1
Corporate and other expenses		20.5						(1.9	) (i)		18.6
Financing costs		35.5									35.5
Total expenses	$	1,440.3		$	—		$	44.5		$	1,484.8
Net income before tax		80.1			1,638.1			(64.6	)		1,653.6
Income tax expense		(17.8	)		10.7	(h)		5.8	(l)		(1.3	)
Net income	$	62.3		$	1,648.8		$	(58.8	)	$	1,652.3
Net income attributable to non-controlling interests		(9.7	)		9.7	(f)					—
Net income available to common shareholders	$	52.6		$	1,658.5		$	(58.8	)	$	1,652.3
Other comprehensive gain (loss)
Unrealized loss on AFS assets		(96.5	)								(96.5	)
Income tax benefit		8.1									8.1
Currency translation adjustments		(1.1	)		1.1	(d)					—
Total other comprehensive loss	$	(89.5	)	$	1.1		$	—		$	(88.4	)
Comprehensive gain (loss) attributable to common shareholders	$	(36.9	)	$	1,659.6		$	(58.8	)	$	1,563.9
Per share data
Earnings per common share:
Earnings per common share:		0.27									14.91
Earnings per diluted common share		0.26									14.91
Weighted average common shares outstanding		194.3									110.8
Weighted average diluted common shares outstanding		199.4									110.8

Explanatory notes (d), (f), (g) and (h) are contained within note 4 “Transaction Accounting Adjustments” of this unaudited pro forma condensed combined financial information.

Explanatory notes (i) to (m) are contained within note 5 “Autonomous Entity Adjustments” of this unaudited pro forma condensed combined financial information.

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Notes To The Unaudited Pro Forma Condensed Combined Financial Information

Note 1. Basis of Presentation

The accompanying unaudited pro forma condensed combined financial information and related notes have been prepared in accordance with Article 11 of Regulation S-X, as amended by the final rule, Release No. 33-10786 and have been derived from the historical combined financial statements of the Group.

The unaudited pro forma condensed combined financial information reflect pro forma adjustments that are described in the accompanying notes and are based on available information and certain assumptions that the Group believes are reasonable. However, actual results may differ from those reflected in these unaudited pro forma condensed combined financial information. In the Group’s opinion, all adjustments that are necessary to present fairly the pro forma information have been made. The unaudited pro forma condensed combined financial information does not purport to represent what the Group’s financial position or results of operations would have been if the Separation Transactions had actually occurred on the dates indicated above, nor are they indicative of FIHL’s future financial position or results of operations. The unaudited pro forma condensed combined financial information should be read in conjunction with the historical financial statements and related notes thereto for the periods presented, as included elsewhere in this prospectus.

Note 2. Unaudited Pro Forma Condensed Combined Balance Sheet

For purposes of preparing the unaudited pro forma condensed combined balance sheet at December 31, 2022, the Separation Transactions will be accounted for as if they had occurred on December 31, 2022. The unaudited pro forma condensed combined balance sheet includes the impact of the Separation Transactions in respect of the distribution of Fidelis MGU to the FIHL shareholders, resulting in the deconsolidation and consequent elimination of the net assets of Fidelis MGU and its subsidiaries. Refer to note 25 (“Subsequent Events”) of our audited consolidated financial statements contained elsewhere in this prospectus for further information on the accounting treatment of the Separation Transactions.

As discussed in note 25 (“Subsequent Events”) of our audited consolidated financial statements contained elsewhere in this prospectus, following the consummation of the Separation Transactions, Fidelis MGU acquired 9.9% of the Common Shares of FIHL. Such Common Shares were acquired in private transactions with the Group’s shareholders and did not impact the number of issued and outstanding Common Shares or the cash flows of the Group. Accordingly, these sales by shareholders are not reflected within this pro forma condensed combined balance sheet.

Note 3. Unaudited Pro Forma Condensed Combined Statement of Operations

For the purposes of preparing the unaudited pro forma condensed combined statement of operations for the year ended December 31, 2022, the autonomous entity adjustments are accounted for as if they had occurred on January 1, 2022. With respect to the transaction accounting adjustments, we have also taken account of the impact of additional expenses that were incurred from the consummation of the Separation Transactions.

Note 4. Transaction Accounting Adjustments

The unaudited pro forma condensed combined balance sheet and statement of operations include the following transaction accounting pro forma adjustments:

a. To reflect the removal of the assets and liabilities of Fidelis MGU.

We note that premiums and other receivables have increased by $9.3 million. This amount represents premiums receivable that were collected by Pine Walk Capital from third parties on or prior to December 31, 2022 but not remitted to the insurance operating subsidiaries of the Group. In the pro forma condensed combined balance sheet, these amounts have been reclassified from cash and cash equivalents to premiums and other receivables.

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b. To reflect the impact on cash and cash equivalents of the removal of Fidelis MGU in the amount of $111.6 million plus the payment of various expenses and employee tax on net settled share compensation awards related to the Separation Transactions in the amount of $119.9 million.

c. To reflect the impact on additional paid-in capital of the transaction accounting adjustments.

d. To reflect the elimination of the currency translation adjustment of Fidelis MGU.

e. To reflect the impact on accumulated deficit of the transaction accounting adjustments. The following table shows a reconciliation from our U.S. GAAP accumulated deficit to the pro forma accumulated deficit (amounts expressed in millions of U.S. dollars):

	December 31, 2022
Accumulated deficit at December 31, 2022		0.5
Fair value of Fidelis MGU at January 3, 2023		1,775.0
Net assets of Fidelis MGU		(68.8	)
Expenses of Separation Transactions		(68.1	)
Net gain on distribution of Fidelis MGU		1,638.1
Fair value of Fidelis MGU at January 3, 2023		1,775.0
Net assets of Fidelis MGU		(68.8	)
Distribution of Fidelis MGU to common shareholders		(1,706.2	)
Tax impact of Transaction Accounting adjustments		10.7
Elimination of non-controlling interests		10.3
Pro forma accumulated deficit		(46.6	)

f. To reflect the elimination of the non-controlling interests following the distribution of Pine Walk Capital Limited and its subsidiaries as part of the Separation Transaction.

g. To reflect the net gain on distribution of Fidelis MGU. The gain has been calculated as the fair value of Fidelis MGU of $1,775 million, less the net assets of Fidelis MGU of $68.8 million and less the direct costs of the Separation Transactions of $68.1 million. Refer to note 25 (“Subsequent Events”) of our audited consolidated financial statements contained elsewhere in this prospectus for further information on the accounting treatment of the Separation Transactions.

We have determined the fair value of Fidelis MGU in accordance with the requirements of Financial Accounting Standards Board Accounting Standards Codification 820 – Fair Value Measurements (“ASC 820”). We have obtained the services of a third-party independent valuation expert in arriving at that determination of fair value. ASC 820 explains the concept of fair value for financial reporting. Under ASC 820, fair value is a market-based measurement, not an entity specific measurement. The objective of ASC 820 is to estimate the price at which an orderly transaction to sell the asset would take place between market participants at the measurement date under current market conditions (that is, an exit price at the measurement date from the perspective of a market participant).

When a price for an identical asset is not observable, a reporting entity measures fair value using another valuation technique that maximizes the use of relevant observable inputs and minimizes the use of unobservable inputs. Fair value is measured using the assumptions that market participants would use when pricing the asset or liability, including assumptions about risk.

For purposes of our valuation of Fidelis MGU, we have used an income approach using a discounted cash flow methodology, and a market approach using comparable listed trading and precedent transaction multiples. These approaches generated a range of values for Fidelis MGU of $1.7 billion to $1.9 billion. Our determined fair value for Fidelis MGU of $1.775 billion was based on the price of the most recent transactions in Fidelis MGU shares, and close to the mid-point of the valuation range. On January 3, 2023, following the distribution of Fidelis MGU to shareholders of the Group, certain

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shareholders sold their shares, and certain third parties purchased shares, in Fidelis MGU at a price per share determined using a fair value of $1.775 billion.

h. To reflect the income tax effect of the adjustments discussed above, determined using the applicable statutory tax rates of the United Kingdom, Ireland and Bermuda for the year then ended.

Note 5. Autonomous Entity Adjustments

The unaudited pro forma condensed combined statement of operations includes the following autonomous entity pro forma adjustments:

i. To reflect the elimination of Fidelis MGU from our combined statement of operations. This includes the profit commission payable to Fidelis MGU, which was recorded as part of GPW, that was previously eliminated on consolidation. We have also removed the impact of amounts earned and expensed by Fidelis MGU for net investment income, net foreign exchange gains, other income and corporate expenses.

j. To reflect the effects of the Framework Agreement. Included in the unaudited pro forma condensed combined statement of operations for the year ended December 31, 2022 is an adjustment that reflects incremental commissions associated with underwriting origination performed by Fidelis MGU. The incremental cost represents commissions payable to Fidelis MGU as a percentage of net premiums written on business originated by Fidelis MGU from January 1, 2022. This also includes commission payable to Fidelis MGU subsidiaries, Pine Walk Capital and Pine Walk Europe, that was previously eliminated on consolidation. The amounts calculated assume the commissions that would have been payable to Fidelis MGU for all business written in 2022. The commission payable is deferred and amortized over the related policy period in line with earned premiums. The commission percentage payable to Fidelis MGU will depend on whether the business was sourced in the open market, was sourced by Fidelis MGU via an existing underwriting origination contract with third-party managing general underwriters or has been placed with the Group from subsidiary cells of Pine Walk Capital and Pine Walk Europe.

We have also reflected incremental portfolio management fees payable to Fidelis MGU as a percentage of net premiums written. The portfolio management fee payable is deferred and amortized over the related policy period in line with earned premiums.

The total of such commissions and portfolio management fee is $119.5 million.

We have reclassified the commissions on ceded business of $61.7 million from general and administrative expenses to policy acquisition expenses. This adjustment has been made to ensure consistency with the presentation of commissions on ceded business in our unaudited consolidated financial statements for the three months ended March 31, 2023 and 2022 (see note 2, Significant Accounting Policies). We have deducted the proportion of the commissions on ceded business of $23.9 million that will be received by Fidelis MGU. The Framework Agreement provides that in respect of commissions on ceded quota share business the Group shall retain 1.0% of reinsurance premiums ceded and the remainder is to be paid to Fidelis MGU. This adjustment only considers the 2022 year of account as all overrider commissions receivable on business ceded in prior years of account will remain to the account of FIHL.

k. Included in the unaudited pro forma condensed combined statement of operations for the year ended December 31, 2022 is a net decrease to general and administrative expenses that reflects:

i. the elimination of the direct staff costs and costs of services of $122.2 million resulting from the deconsolidation of Fidelis MGU.

ii. the incremental costs of additional staff and services of $21.7 million required by FIHL necessary to undertake certain functions as a standalone entity independent of Fidelis MGU.

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iii. the effects of the Inter-Group Services Agreement. This reflects the incremental costs of $3.5 million associated with certain finance, human resources and IT services that will be provided by Fidelis MGU. The level of the service costs payable to Fidelis MGU will ultimately depend on the extent of the services that are to be provided.

iv. the reclassification of commissions on ceded business of $61.7 million to policy acquisition expenses.

l. To reflect the income tax effect of the autonomous entity adjustments, determined using the applicable statutory tax rates of the United Kingdom, Ireland and Bermuda for the year then ended.

m. The elimination of profit commissions incurred on certain existing quota share reinsurance contracts ceded to third party reinsurers that will instead be received by Fidelis MGU. This adjustment relates to the 2022 year of account as all profit commissions receivable on business ceded in prior years of account will be earned by FIHL.

Note 6. Earnings per share

The Separation Transactions resulted in the accelerated vesting and exercise of all restricted stock units and in-the-money warrants, with an additional 13,553,681 Common Shares being issued on January 3, 2023. The distribution of Fidelis MGU to shareholders of FIHL resulted in the cancellation of 97,327,049 Common Shares, with 110,771,897 Common Shares remaining.

Our earnings per share has been restated to take account of the impact on net income available to common shareholders of the transaction accounting and autonomous entity adjustments. We have also restated our basic and diluted shares to reflect the Common Shares in issuance after the Separation Transactions. As all restricted stock units and warrants were issued and exercised as part of the Separation Transactions, our pro-forma basic and diluted earnings per share are equal.

Note 7. Impact on Performance Measures and non-U.S. GAAP financial measures

Below is a description of our unaudited pro forma performance measures and pro forma non-U.S. GAAP financial measures. Our pro forma non-U.S. GAAP financial measures are not measures of financial performance under U.S. GAAP and should not be construed as a substitute for the most directly comparable pro forma U.S. GAAP measures, which are reconciled below. These measures have limitations as analytical tools, and when assessing our operating performance, you should not consider these measures in isolation or as a substitute for GAAP measures. Other companies may calculate these measures differently than we do, limiting their usefulness as a comparative measure. Please refer to “Management’s Discussion and Analysis of Financial Condition and Results of Operations – Performance Measures and Non-U.S. GAAP Financial Measures” for further details as to how we calculate these measures and why we believe they are meaningful.

We have not presented a pro forma net investment return percentage and total investment return percentage as the impact of the pro forma adjustments on these performance measures was 0.0% and 0.1%, respectively.

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The table below shows the impact on our loss ratio, expense ratio and combined ratio of the pro forma adjustments discussed in notes 4 and 5 above ($ in millions unless stated in percentages):

	For the Year Ended December 31, 2022
	Pro Forma
Losses and loss adjustment expenses	$	830.2
Pro forma policy acquisition expenses		409.9
Pro forma Fidelis MGU commissions		119.5
Pro forma general and administrative expenses		71.1
Pro forma total underwriting expenses	$	600.5
Net premiums earned	$	1,489.0
Pro forma loss ratio		55.8	%
Pro forma expense ratio		40.3	%
Pro forma combined ratio		96.1	%

The table below shows the impact on our operating net income, RoE and our Operating RoE of the pro forma adjustments discussed in notes 4 and 5 above ($ in millions unless stated in percentages):

	For the Year Ended December 31, 2022
	Pro Forma
Opening common shareholders’ equity		2,013.9
Pro forma net income available to common shareholders	$	1,652.3
Add back: net foreign exchange gains		(4.1	)
Add back: corporate and other expenses		18.6
Add back: net gain on distribution of Fidelis MGU		(1,638.1	)
Tax impact of the above		(12.2	)
Pro forma operating income	$	16.5
Pro forma RoE		82.0	%
Pro forma Operating RoE		0.8	%

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MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

The following is a discussion and analysis of our financial condition and results of operations. This discussion and analysis should be read in conjunction with the section entitled “Unaudited Pro Forma Condensed Combined Financial Information,” as well as our audited consolidated financial statements for those respective periods and related notes contained therein, which are contained elsewhere in this prospectus. This discussion and analysis contains forward-looking statements that involve risks and uncertainties and that are not historical facts, including statements about our beliefs and expectations. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including those discussed below and in this prospectus under the headings “Risk Factors,” “Business” and “Cautionary Statement Regarding Forward-Looking Statements.”

Overview

Fidelis is a global (re)insurance company, with operations in Bermuda, Ireland and the United Kingdom. FIHL was formed in Bermuda in 2014 by Richard Brindle, under the principles of focused, process-driven and disciplined underwriting and risk selection, strong client and broker relationships and nimble capital deployment. Fidelis completed its initial funding and began underwriting business in June 2015 under the direction of an experienced management team led by Richard Brindle. Since then, Fidelis has assembled a diversified global book of (re)insurance business and achieved scale as a specialty (re)insurer with GPW of $3.0 billion, total revenues of $1.5 billion and net income of $62.3 million for the year ended December 31, 2022.

On January 3, 2023, the Separation Transactions were completed and two distinct holding companies and businesses were created: FIHL and MGU HoldCo. FIHL is the parent holding company for Current Fidelis, is the issuer of the Common Shares sold by the Selling Shareholders in this offering and continues to own all of the insurance operating subsidiaries of Current Fidelis, comprised of FIBL, FUL and FIID. Current Fidelis also has its own service company, FIHL (UK) Services, with a branch in Ireland.

MGU HoldCo is the parent holding company for Fidelis MGU that carries on the origination and underwriting activities on behalf of Current Fidelis and is led by Mr. Brindle. MGU HoldCo’s principal operating subsidiaries are Bermuda MGU, Pine Walk Capital and Pine Walk Europe. The underwriting activities of each of the licensed insurance carriers of Current Fidelis (FIBL, FUL and FIID) are outsourced to the corresponding operating subsidiaries of Fidelis MGU on a jurisdictional basis (Bermuda MGU, Pine Walk Capital and Pine Walk Europe, respectively). Each of the operating subsidiaries of Fidelis MGU has delegated underwriting authority to source and bind contracts for and on behalf of each of FIBL, FUL and FIID, respectively. See “Material Contracts and Related Party Transactions—Framework Agreement.” MGU HoldCo and its subsidiaries will not be consolidated with FIHL and its subsidiaries.

FIHL and MGU HoldCo have entered into the Framework Agreement that governs the ongoing relationship between the two groups of companies (see “Business—Our Corporate Structure” for additional details). Following consummation of the Separation Transactions on January 3, 2023, Mr. Brindle’s employment agreement and the employment agreements of certain other senior management and other employees of Previous Fidelis are with FML, and Mr. Brindle is now the Chairman and Chief Executive Officer of Fidelis MGU. See “The Separation Transactions.”

The Separation Transactions allow FIHL to access the underwriting expertise of Fidelis MGU while allowing Fidelis MGU to attract and retain highly sophisticated underwriting talent, including Mr. Brindle and senior underwriters. We believe that the Separation Transactions and the Framework Agreement have structural benefits for both groups of companies, including increased flexibility to quickly respond to evolving insurance and reinsurance market conditions and help sustain our strong underwriting results through access to top talent. Our objective following the completion of the Separation Transactions remains to further solidify Fidelis’ position as a sophisticated bespoke and specialty underwriter.

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History

FIHL was established on August 22, 2014 and in 2015 raised $1.5 billion of ordinary equity capital to support its underwriting plans. Following further capital raises in 2019, 2020 and 2021, at December 31, 2022 Fidelis had $1,976.8 million of shareholders’ equity, $58.4 million of Series A Preference Securities and $447.5 million of long-term debt.

Through FIBL and FUL, Fidelis has offices in Bermuda and London, which we consider to be the largest specialty (re)insurance hubs globally. Fidelis also accesses the E.U. through FIID, which has an office in Ireland.

FIBL is a wholly owned subsidiary of FIHL and was incorporated as an exempted company under the laws of Bermuda on February 26, 2015 and is registered as a Class 4 insurer. FIBL predominantly writes property insurance and reinsurance on a global basis along with certain Bespoke and Specialty lines. FUL is a wholly owned subsidiary of FIHL and was incorporated on August 28, 2015 under the laws of England and Wales. FUL writes predominantly Bespoke and Specialty insurance on a global basis and writes a smaller portion of property reinsurance business relative to FIBL. FIID is an indirect wholly owned subsidiary of FIHL and was incorporated under the laws of Ireland on December 27, 2017. FIID writes Fidelis’ European Bespoke and Specialty business. As part of its Brexit planning, on March 29, 2019, FIID accepted non-U.K. E.U. insurance policies from FUL through a Part VII transfer under the U.K.’s Financial Services and Markets Act of 2000 in preparation for the U.K.’s exit from the E.U.

The following discussion and analysis relates to our historical financial results for periods prior to the completion of the Separation Transactions on January 3, 2023, pursuant to which two distinct holding companies and businesses were created, FIHL and MGU HoldCo. FIHL is the parent holding company for Current Fidelis and owns all of the current operating insurance companies of Current Fidelis and is the issuer of the Common Shares sold by the Selling Shareholders in this offering. MGU HoldCo is the parent holding company for Fidelis MGU, the managing general underwriter platform that will lead the origination and underwriting activities of Current Fidelis. Fidelis MGU is led by Mr. Brindle. See “The Separation Transactions” for further details.

Strategy

Our strategy is to match adequately priced risks with efficient sources of capital to produce strong returns for shareholders.

Fidelis MGU will originate business from multiple sources including brokers, third-party delegated underwriting, existing capital relationships, and open market business originated by its underwriters. Historically, 70.0% of NPW has been sourced in open market activities, with the remainder sourced equally from the existing Pine Walk Capital relationships and third-party managing general underwriters.

Fidelis’ business consists of the following reportable segments or ‘pillars’: Specialty, Bespoke, and Reinsurance.

Fidelis believes that the most effective operating model for a (re)insurance group is to enter into long-term agreements with strategic outsource providers. This operating model will allow us to manage operating expenses effectively and to access strong underwriting, risk management and information technology systems and data. See “Business—Strategic Relationship with the MGU” and “Material Contracts and Related Party Transactions” for more information.

We have incurred costs engaging external advisors to assist in the planning and execution of the Separation Transactions (the “Separation Costs”). For further detail on the Separation Transactions, see “The Separation Transactions.” The Separation Costs include, among other things, legal and professional fees. All Separation Costs were incurred prior to consummation of the Separation Transactions and are not expected to reoccur. See “Unaudited Pro Forma Condensed Combined Financial Information” for the impact of the Separation Transactions on the consolidated financial statements of FIHL.

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Fidelis’ Year in Review for 2022

2022 saw continued growth in our GPW to $3,000.1 million from $2,787.7 million in 2021, driven by our Bespoke and Specialty segments. Following another year of continued elevated catastrophe losses in 2021, we significantly reduced the 2022 GPW in our Reinsurance segment. Our combined ratio was slightly lower than the prior year, at 92.1% in 2022 compared to 92.9% in 2021. This was driven by a decrease in our Reinsurance segment loss ratio to 74.3% from 114.2%, partially offset by large losses of $135 million in relation to the Ukraine Conflict. Increases in interest rates generated realized and unrealized losses on investments in 2022, and our income tax expense increased due to more profits being earned in taxable jurisdictions. Our Operating RoE was 3.3% in 2022 compared with 3.6% in 2021.

Following another year of worldwide natural catastrophe losses in excess of $100 billion we have reduced our Reinsurance GPW along with the related exposure. Working with our underwriting, actuarial and modelling teams, as well as external consultants, we developed a proprietary Fidelis View of Risk, which incorporates a science-based estimation of the impact of climate change on atmospheric perils and has meaningfully increased the modeled losses across a range of coverages such as convective storms, floods and wildfires. As a result, we believe the Fidelis View of Risk has the potential to more accurately reflect potential expected losses, compared to industry models and we consider this when pricing and underwriting our risks.

Additionally, we have looked at lessons learned about the wide variance in ceding insurers’ loss estimation and adjustment capabilities, as well as financial capacity, and we plan to reduce exposure to property treaty clients who score poorly in these assessments. In 2022 this led us to reduce our catastrophe treaty excess-of-loss writings to deploy less capacity to layers that are more exposed to increased frequency of atmospheric peril losses, and to increase pricing on these lines. With respect to loss handling, we see better alignment with our clients in our property D&F portfolio and we view this as a better way to deploy natural catastrophe capacity at this stage of the (re)insurance cycle.

Our swift action in positioning our portfolio for our view of coming market trends is emblematic of our approach to being proactive in acknowledging and responding to new data and information. 2019 and prior years saw softer market conditions, for instance, in 2019, as a reflection of the soft rate market conditions in specialty, our business mix was allocated 57.5% (by NPW) to our Bespoke pillar and only 11.9% (by NPW) to our Specialty pillar. The hardening Specialty rate environment in 2020 and Bespoke risks associated with the economic cycle and the COVID-19 pandemic drove us to rebalance the portfolio mix with Specialty representing 44.5% of NPW. We believe the reallocation of our Reinsurance appetite offers an attractive risk-adjusted return under current market conditions.

Bespoke and Specialty business accounted for 87.2% of our portfolio (by NPW) in 2022 and we expect to see continued market hardening across most lines. We paused the growth of our Bespoke book in 2020 as we assessed the impact of the downturn in the economy from COVID-19. Our Bespoke products proved resilient to the economic downturn, and as the economy started to pick up again, we saw a resumption in the growth trajectory of our Bespoke business in 2022 and 2021 and are pleased with the performance of our portfolio.

We have continued to build out our operational teams and underwriting tools including our analytical and aggregation system FireAnt (which we license from Fidelis MGU following the consummation of the Separation Transactions).

We have continued our cautious stance on investments, focusing on a high credit quality, short-duration core fixed maturity strategy.

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Current Outlook, Market Conditions and Rate Trends

The global reinsurance and insurance business is highly competitive, and cyclical by product and market. As such, financial results tend to fluctuate between periods of constrained capital availability and associated higher premium rates and stronger profits followed by periods of abundant capacity, lower rates and constrained profitability. The fluctuation of these market conditions may affect demand for our products, the premiums we charge, the terms and conditions of the (re)insurance policies we write and changes in our underwriting strategy.

A substantial component of our business is influenced by other factors such as the frequency and/or severity of underwriting losses, including natural disasters or other catastrophic events, pandemics, variations in interest rates and financial markets, changes in the legal, regulatory and judicial environments, inflationary pressures and general economic conditions. These factors influence, among other things, the demand for and profitability of our products. Consequently, there will be a degree of volatility in our financial results based upon the frequency and severity of losses that occur and to which we are exposed. See “Risk Factors.”

Premium Environment and Cycle: Premiums typically rise in response to losses, which leads to higher profitability and in turn attracts new capital into the insurance market to support underwriting. This additional influx of capital then typically leads to reduced rates and softening prices over time.

The global Specialty market rate growth has been strong in recent years. For example, Lloyd’s risk-adjusted rate change increased by 7.7% for 2022 versus the prior year, and cumulatively increased by 43.9% from 2018. We believe these favorable underwriting conditions are expected to continue in the near term as a result of the interaction between the supply of new capital and continued claims trends and development. See “Business—Insurance Market Conditions.”

Claims Experience and Pricing Support: In recent years, climate change has driven an increase in the frequency and severity of catastrophe events which we believe has increased the claims experience of property and specialty (re)insurers, including us. The effects of these claims have been exacerbated by the impact of other climate-related losses such as wildfires and floods.

We believe that claims experience has also been affected by “social inflation,” which is driving claims costs over and above economic inflation as a result of increasing societal trends towards higher litigation costs and jury awards. Additionally, certain economic, social and political events, such as the COVID-19 pandemic and other public health crises have had a material effect on supply chains affecting the availability and pricing of underlying raw materials, which led to issues for (re)insurance companies paying out on claims. Furthermore, the Ukraine Conflict has led to widespread disruption in the upstream supply chains for oil, gas and certain agricultural commodities, putting further pressure on the challenges facing the (re)insurance industry. While the length and severity of the strain the supply chains are under is unknown, a prolonged period of disruptions may have a material adverse effect on the (re)insurance industry’s ability to pay out on claims both in terms of monetary costs as well as availability of the underlying goods and services necessary for the payout. See “Risk Factors—Risks Related to Recent Events.”

Furthermore, in recent years, we believe favorable prior year claims development and associated loss reserve releases (which is a key driver of recent profitability) have declined. This claims development and reserve release pattern suggests that underwriters will need to maintain underwriting discipline to maintain profitability, which may result in a prolonged hard rate environment.

However, while there is naturally some uncertainty as to future rate developments, we believe that there is sufficient support, driven by a number of factors, to expect continued rate hardening in the near term in many (re)insurance classes in which we participate. With the Ukraine Conflict, for example, a number of lines within Specialty and Bespoke could be exposed to potential losses, adding further momentum to continuing rate increases. See “Risk Factors—Risks Relating to Recent Events.”

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COVID-19: We have performed an analysis to estimate potential exposure to property business interruption losses from the COVID-19 pandemic. In general, our property reinsurance portfolio is more focused on residential exposure rather than commercial and the vast majority of cedants have strong exclusions in place. This reduces the potential for losses through property business interruption. At December 31, 2022 we had estimated loss reserves of $15.2 million in our reserves for Business Interruption losses relating to the COVID-19 pandemic. Areas within our financial statements that have a potential to be impacted by the continued uncertainty related to the effects of the COVID-19 pandemic include valuation of the investment portfolio and net reserves for losses and loss adjustment expenses. The potential for losses arising from the COVID-19 pandemic have been and will continue to be monitored.

Effects of Inflation: General economic inflation has increased and there is a risk of inflation remaining elevated for an extended period, which could cause claims and claim expenses to increase, impact the performance of our investment portfolio or have other adverse effects. See “Risk Factors—Risks Relating to Recent Events—The current inflationary environment could have a material adverse impact on the Group’s operations.”

The impact of inflation on Fidelis’ results cannot be known with any certainty; however, we have considered the possible effects of inflation in catastrophe loss models and on our investment portfolio. Furthermore, our estimates of the potential effects of inflation are also considered in pricing and in estimating reserves for unpaid claims and claim expenses. The actual effects of inflation on our results cannot be accurately known until claims are ultimately resolved. See “Risk Factors—Risks Relating to Recent Events” and “Risk Factors—Risks Relating to Financial Markets and Liquidity.”

Competitive Landscape: While Fidelis’ market share of the global specialty market is small, we believe Fidelis has an appreciable share of the niche markets in which it participates. This approach is consistent with our strategy of participating in classes where Fidelis believes it has a competitive advantage or sees pricing opportunities.

We deploy large line sizes in these classes opportunistically to extract preferential terms and rates over our peers. The ability to write large line sizes means Fidelis is able to assume a significant exposure under a single insurance policy. These large line sizes are more attractive to brokers as they minimize the number of underwriters with whom they must negotiate and provide us with greater leverage for preferable pricing and terms.

Our management team believes that it is well positioned to take advantage of the ongoing rate hardening in the key markets in which we participate and will continue to address and respond to the ongoing uncertainties presented by the challenges facing the (re)insurance industry.

Recent Developments and Activity

The Ukraine Conflict began on February 24, 2022 and subsequently the E.U. and a number of other countries, including the U.S. and the U.K., placed significant sanctions on Russian institutions and persons that resulted in a devaluation of the ruble and a fall in the value of Russian fixed maturity and equity assets, as well as the prompt withdrawal of certain companies from Russia without securing their assets. Fidelis has potential exposure to losses associated with the Ukraine Conflict through certain lines in its Bespoke and Specialty segments. For example, as a result of the aircraft lessor claims, and related proceedings, on account of the unreturned aircraft in Russia, provision has been made in the Group’s reserves as of March 31, 2023 in the amount of $145.6 million for any potential exposures relating to the Ukraine Conflict, the majority of which is related to leased aircraft in Russia. Any related exposure remains subject to a number of complexities and implications subject to ongoing evaluation and determination. For additional information, see the risk factors titled “The full extent of the impacts of the ongoing Ukraine Conflict on the (re)insurance industry and on the Group’s business, financial condition and results of operations, including in relation to claims under the Group’s (re)insurance policies, are uncertain and remain unknown.” and “We may be subject to litigation which could adversely affect our business.”

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The final cost may be different from the current reserving estimate due to the uncertainty associated with any change in the political situation, the ultimate outcome of the litigation matters, the asset valuation process, the unique issues as to scope of coverage and the outcome of explorative discussions underway between Western aircraft lessors and Russian airline operators for the sale of some of the unreturned aircraft. Based on our knowledge and assessment of current events, we do not believe that the Ukraine Conflict will adversely affect our ability to operate as a going concern.

Performance Measures and Non-U.S. GAAP Financial Measures

In presenting our results, management has included certain non-U.S. GAAP financial measures that we believe are useful to consider, in addition to our U.S. GAAP results, for a more complete understanding of the financial performance and position of FIHL. The key financial U.S. GAAP and non-U.S. GAAP measures that we believe are meaningful in analyzing our performance are summarized below and where applicable a reconciliation of non-U.S. GAAP measures to U.S. GAAP financials is set out. However, any non-U.S. GAAP measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP and our methodology for calculating these measures may be different from the way our industry peers calculate these measures.

• Loss Ratio: is a measure of the losses that have been incurred by the business compared to the premiums that have been recorded to cover those losses and is expressed as a percentage of the losses and loss adjustment expenses divided by NPE. The losses will be affected by the occurrence and frequency of catastrophe events, the volume and severity of non-catastrophe losses and the extent of any outwards reinsurance that has been put in place to mitigate the effect of those losses. The loss ratio in 2022 of 55.2% was primarily impacted by the ongoing Ukraine Conflict. The loss ratio in 2021 of 60.4% was impacted by significant catastrophes that occurred in 2021, including Winter Storm Uri, Hurricane Ida, Storm Bernd and the U.S. Midwest tornados that occurred in December 2021. The loss ratio of 44.5% in 2020 was primarily driven by the impact of Hurricane Laura and the U.S. Midwest derecho and COVID-19 losses.

• Accident Year Loss Ratio Excluding Catastrophes, Large Losses and Prior Year Reserve Movements: is a non-U.S. GAAP measure of the representation of the loss ratio excluding the impact of catastrophes, large losses and prior year reserve movements, and supports meaningful comparison between periods. Accident year loss ratio excluding catastrophes, large losses and prior year reserve movements is calculated by dividing net incurred losses and loss adjustment expenses excluding catastrophes, large losses and prior year reserve movements by net premiums earned excluding catastrophe-related reinstatement premiums. Our large losses and catastrophe losses in 2022 included Australia floods, European storms, Hurricane Ian and the Russian invasion of Ukraine. Our large losses and catastrophe losses in 2021 included Winter Storm Uri, Hurricane Ida and Storm Bernd. Our large losses and catastrophe losses in 2020 included Hurricane Laura and the U.S. Midwest derecho. Our accident year loss ratio excluding catastrophes, large losses and prior year reserve movements in 2022 was 31.5% compared with 27.4% in 2021. A key factor in the increase in the ratio is the changing underlying mix of our portfolio. In 2022 we grew our Specialty segment and began to reduce our Reinsurance segment exposure. The Specialty segment has a higher attritional loss ratio than the Reinsurance segment, which is more catastrophe exposed. Our accident year loss ratio excluding catastrophes, large losses and prior year reserve movements in 2021 of 27.4% increased from 25.8% in 2020. This was driven by the growth in our Specialty segment over this period and its higher attritional loss ratio than our catastrophe-driven Reinsurance segment.

• Underwriting Ratio: is a measure of the underwriting performance and is expressed as a percentage of the losses and loss adjustment expenses plus the commissions that are paid to brokers and delegated underwriters that source the business on our behalf divided by earned premium, net of reinsurance. Our underwriting ratio of 85.0% decreased from 86.4% in 2021 driven by a decrease in our Reinsurance segment underwriting ratio. Our underwriting ratio of 86.4% in 2021 increased from 69.1% in 2020, primarily driven by increased natural catastrophe loss activity in 2021.

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• Expense Ratio: is a measure of the extent of the commissions that are paid to brokers and delegated underwriters that source the business on our behalf plus the general and administrative expenses that are incurred to run the business compared to the amount of premium that is earned. Overrider income earned on business ceded to third party reinsurers is credited to general and administrative expenses. The expense ratio is expressed as a percentage and is the ratio of policy acquisition expenses (net of ceded reinsurers’ share of acquisition costs) and general and administrative expenses to net premiums earned. Our expense ratio in 2022 was 36.9% compared with 32.5% in 2021. The increase is partly caused by the increase in net premiums earned in our Bespoke segment which has higher ceding commissions than our other segments, and higher professional fees within our general and administrative expenses. Our expense ratio was 32.5% in 2021 compared with 36.1% in 2020.

• Combined Ratio: is a measure of our underwriting profitability and is expressed as the sum of the loss ratio and expense ratio. A combined ratio under 100% indicates an underwriting profit, while a combined ratio over 100% indicates an underwriting loss. Our combined ratio decreased to 92.1% in 2022 from 92.9% in 2021, primarily driven by a lower loss ratio in our Reinsurance segment. Our combined ratio of 92.9% in 2021 increased from 80.6% in 2020, primarily driven by increased natural catastrophe loss activity in 2021.

The table below reconciles our accident year loss ratio excluding catastrophes, large losses and prior year reserve movements to losses and loss adjustment expenses, loss ratio, expense ratio and combined ratio for the years ended December 31, 2022, 2021, and 2020:

	Year Ended December 31,
	2022			2021			2020
	($ in millions unless stated in percentages)
Catastrophe and large losses	$	378.9		$	389.6		$	175.3
Prior year releases		(22.1	)		(9.6	)		(38.4	)
Attritional losses		473.4			316.8			187.6
Losses and loss adjustment expenses	$	830.2		$	696.8		$	324.5
Policy acquisition expenses		447.7			299.9			179.2
General and administrative expenses		106.4			75.4			83.5
Net premiums earned		1,504.7			1,154.2			728.6
Catastrophe and large loss impact on loss ratio		25.1	%		33.8	%		24.1	%
Prior year release impact on loss ratio		(1.5	%)		(0.8	%)		(5.3	%)
Accident year loss ratio excluding catastrophes, large losses and prior year reserve movements		31.5	%		27.4	%		25.7	%
Loss ratio		55.1	%		60.4	%		44.5	%
Underwriting ratio		85.0	%		86.4	%		69.1	%
Expense ratio		36.9	%		32.5	%		36.1	%