enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement June 30, 2022

| enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 4 Consolidated Results by Segment 5 Capital Position & Credit Ratings 9 Non-GAAP Measures 10 Reconciliation to Adjusted Book Value per Share 12 Reconciliation to Adjusted Return on Equity 13 Reconciliation to Adjusted Run-off Liability Earnings 14 Reconciliation to Adjusted Total Investment Return 16 Investable Assets - Management’s View 17

| enstargroup.com 3 Explanatory Notes About Enstar Enstar is a NASDAQ-listed leading global (re)insurance group that offers innovative capital release solutions through its network of group companies in Bermuda, the United States, the United Kingdom, Continental Europe, Australia, and other international locations. A market leader in completing legacy acquisitions, Enstar has acquired over 110 companies and portfolios since its formation in 2001. For further information about Enstar, see www.enstargroup.com. Basis of Presentation In this Investor Financial Supplement, the terms "we," "us," "our," "Enstar," or "the Company" refer to Enstar Group Limited and its consolidated subsidiaries. All information contained herein is unaudited. Unless otherwise noted, amounts are in millions of U.S. Dollars, except for share and per share amounts. Certain prior period comparatives have been reclassified to conform to the current presentation. This Investor Financial Supplement is being provided for informational purposes only. It should be read in conjunction with documents filed by Enstar with the U.S. Securities and Exchange Commission, including its Annual Reports on Form 10-K and its Quarterly Reports on Form 10-Q. Non-GAAP Financial Measures In addition to our key financial measures presented in accordance with GAAP, we present other non-GAAP financial measures that we use to manage our business, compare our performance against prior periods and against our peers, and as performance measures in our incentive compensation program. These non-GAAP financial measures provide an additional view of our operational performance over the long-term and provide the opportunity to analyze our results in a way that is more aligned with the manner in which our management measures our underlying performance. The presentation of these non-GAAP financial measures, which may be defined and calculated differently by other companies, is used to enhance the understanding of certain aspects of our financial performance. It is not meant to be considered in isolation, superior to, or as a substitute for the directly comparable financial measures prepared in accordance with GAAP. We have presented the results and GAAP reconciliations for these measures. Refer to pages 10 to 18 for further details. Cautionary Statement This Investor Financial Supplement contains certain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. These statements include statements regarding the intent, belief or current expectations of Enstar and its management team. Investors are cautioned that any such forward- looking statements speak only as of the date they are made, are not guarantees of future performance and involve risks and uncertainties, and that actual results may differ materially from those projected in the forward-looking statements as a result of various factors. Important risk factors regarding Enstar can be found under the heading "Risk Factors" in our Form 10-K for the year ended December 31, 2021 and are incorporated herein by reference. Furthermore, Enstar undertakes no obligation to update any written or oral forward-looking statements or publicly announce any updates or revisions to any of the forward-looking statements contained herein, to reflect any change in its expectations with regard thereto or any change in events, conditions, circumstances or assumptions underlying such statements, except as required by law.

| enstargroup.com 4 Three Months Ended Six Months Ended June 30, 2022 June 30, 2021 June 30, 2022 June 30, 2021 Key Earnings Metrics Return on equity (“ROE”) (9.8) % 6.0 % (13.9) % 9.1 % Annualized ROE (27.7) % 18.2 % Adjusted ROE (1) (4.2) % 10.9 % Annualized adjusted ROE (1) (8.4) % 21.7 % Basic net (loss) earnings per share $ (28.62) $ 17.44 $ (44.54) $ 25.95 Diluted net (loss) earnings per share $ (28.62) $ 17.28 $ (44.54) $ 25.60 Key Run-off Metrics Average net loss reserves $ 11,897 $ 9,690 Annualized Run-off liability earnings (“RLE”) 3.7 % 2.5 % Average adjusted net loss reserves (1) $ 11,963 $ 9,502 Annualized adjusted RLE (1) 0.5 % 1.1 % Key Investment Return Metrics Average aggregate invested assets $ 20,464 $ 18,636 Annualized total investment return (“TIR”) (8.1) % 6.8 % Annualized investment book yield 2.32 % 2.65 % 2.03 % 2.24 % Earnings from equity method investments $ 32 $ 115 Adjusted average aggregate invested assets (1) $ 21,024 $ 18,260 Annualized adjusted TIR (1) (0.8) % 8.0 % Key Shareholder Metrics Ordinary shares repurchased: Shares 535,446 30,364 697,580 48,367 Cost $ 121 $ 7 $ 163 $ 11 Average price per share $ 226.78 $ 237.39 $ 233.92 $ 236.39 As of June 30, 2022 December 31, 2021 Key Shareholder Metrics Ordinary shareholders’ equity $ 4,183 $ 5,586 Total Enstar shareholders’ equity $ 4,693 $ 6,096 Book value per ordinary share (“BVPS”) $ 245.93 $ 316.34 Adjusted BVPS (1) $ 241.05 $ 310.80 Change in adjusted BVPS (22.4) % 10.5 % Total ordinary shares outstanding 17,008,567 17,657,944 Adjusted ordinary shares outstanding 17,353,457 17,973,149 Key Balance Sheet Metrics Total assets $ 23,269 $ 24,429 Debt obligations $ 1,905 $ 1,691 Total liabilities $ 18,209 $ 17,924 Total investable assets to ordinary shareholders’ equity 4.99x 3.89x Total net loss reserves to ordinary shareholders’ equity 2.93x 2.07x Debt to total capitalization attributable to Enstar 28.9 % 21.7 % Financial Highlights (1) Non-GAAP financial measure, refer to pages 10 to 18 for explanatory notes and a reconciliation to the most directly comparable GAAP measure.

| enstargroup.com 5 Consolidated Results by Segment - QTD 2022 Three Months Ended June 30, 2022 Run-off Enhanzed Re Investments Legacy Underwriting Corporate & Other (1) Total INCOME Net premiums earned $ 9 $ 1 $ — $ 4 $ — $ 14 Net investment income — — 104 2 — 106 Net realized losses — — (38) — — (38) Net unrealized losses — — (589) (2) — (591) Other income 7 — — 2 14 23 Total income (loss) 16 1 (523) 6 14 (486) EXPENSES Net incurred losses and loss adjustment expenses Current period 14 — — (1) — 13 Prior period (121) — — 5 37 (79) Total net incurred losses and loss adjustment expenses (107) — — 4 37 (66) Policyholder benefit expenses — 6 — — — 6 Acquisition costs 9 — — 3 — 12 General and administrative expenses 36 2 10 (1) 36 83 Total expenses (62) 8 10 6 73 35 EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 78 (7) (533) — (59) (521) Earnings from equity method investments — — 1 — — 1 SEGMENT EARNINGS (LOSS) $ 78 $ (7) $ (532) $ — (59) (520) Interest expense (23) (23) Net foreign exchange gains 13 13 Income tax benefit 4 4 NET LOSS (526) Net loss attributable to noncontrolling interests 42 42 NET LOSS ATTRIBUTABLE TO ENSTAR (484) Dividends on preferred shares (9) (9) NET LOSS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (32) $ (493) (1) Other income (expense) for corporate and other activities includes the amortization of fair value adjustments associated with the acquisition of DCo, LLC (“DCo”) and Morse TEC LLC (“Morse TEC”). Net incurred losses and loss adjustment expenses for corporate and other activities includes amortization of deferred charge assets (“DCAs”) on retroactive reinsurance contracts and fair value adjustments associated with the acquisition of companies and the changes in the discount rate and risk margin components of the fair value of liabilities related to our assumed retroactive reinsurance agreements for which we have elected the fair value option. The three months ended June 30, 2022 included accelerated amortization of $72 million corresponding to increased favorable prior period development (“PPD”) on net ultimate liabilities recorded in our Run-off segment.

| enstargroup.com 6 Consolidated Results by Segment - QTD 2021 Three Months Ended June 30, 2021 Run-off Investments Legacy Underwriting Corporate & Other (1) Total INCOME Net premiums earned $ 42 $ — $ 17 $ — $ 59 Net investment income — 76 — — 76 Net realized gains — 6 — — 6 Net unrealized gains — 400 — — 400 Other income (expense) 14 — (2) (6) 6 Total income (loss) 56 482 15 (6) 547 EXPENSES Net incurred losses and loss adjustment expenses Current period 42 — 8 — 50 Prior period (59) — 3 46 (10) Total net incurred losses and loss adjustment expenses (17) — 11 46 40 Acquisition costs — — 5 — 5 General and administrative expenses (2) 64 13 1 15 93 Total expenses 47 13 17 61 138 EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 9 469 (2) (67) 409 Loss from equity method investments — (3) — — (3) SEGMENT EARNINGS (LOSS) $ 9 $ 466 $ (2) (67) 406 Interest expense (17) (17) Net foreign exchange gains 10 10 Income tax expense (9) (9) NET EARNINGS 390 Net earnings attributable to noncontrolling interests (3) (3) NET EARNINGS ATTRIBUTABLE TO ENSTAR 387 Dividends on preferred shares (9) (9) NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (95) $ 378 (1) Other income (expense) for corporate and other activities includes the amortization of fair value adjustments associated with the acquisition of DCo and Morse TEC. Net incurred losses and loss adjustment expenses for corporate and other activities includes amortization of DCAs on retroactive reinsurance contracts and fair value adjustments associated with the acquisition of companies and the changes in the discount rate and risk margin components of the fair value of liabilities related to our assumed retroactive reinsurance agreements for which we have elected the fair value option. The three months ended June 30, 2021 included accelerated amortization of $11 million corresponding to increased favorable prior period development PPD on net ultimate liabilities recorded in our Run-off segment. (2) Results for the three months ended June 30, 2021 include incremental expenses attributable to the first quarter 2021 general and administrative expenses following a refinement made to the allocation of expenses in the second quarter of 2021, which increased general and administrative expenses for the Run-off and Investments segments by $16 million and $3 million, respectively, and decreased our corporate and other activities by $19 million.

| enstargroup.com 7 Consolidated Results by Segment - YTD 2022 Six Months Ended June 30, 2022 Run-off Enhanzed Re Investment s Legacy Underwriting Corporate & Other (1) Total INCOME Net premiums earned $ 26 $ 15 $ — $ 7 $ — $ 48 Net investment income — — 180 6 — 186 Net realized losses — — (75) — — (75) Net unrealized losses — — (964) (8) — (972) Other income 17 — — 3 17 37 Total income (loss) 43 15 (859) 8 17 (776) EXPENSES Net incurred losses and loss adjustment expenses Current period 25 — — 1 — 26 Prior period (171) (29) — 4 (26) (222) Total net incurred losses and loss adjustment expenses (146) (29) — 5 (26) (196) Policyholder benefit expenses — 18 — — — 18 Acquisition costs 17 — — 3 — 20 General and administrative expenses 75 4 19 — 70 168 Total expenses (54) (7) 19 8 44 10 EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 97 22 (878) — (27) (786) Earnings from equity method investments — — 32 — — 32 SEGMENT INCOME (LOSS) $ 97 $ 22 $ (846) $ — (27) (754) Interest expense (48) (48) Net foreign exchange gains 10 10 Income tax benefit 4 4 NET LOSS (788) Net loss attributable to noncontrolling interests 31 31 NET LOSS ATTRIBUTABLE TO ENSTAR (757) Dividends on preferred shares (18) (18) NET LOSS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (48) $ (775) (1) Other income (expense) for corporate and other activities includes the amortization of fair value adjustments associated with the acquisition of DCo and Morse TEC. Net incurred losses and loss adjustment expenses for corporate and other activities includes amortization of DCAs on retroactive reinsurance contracts and fair value adjustments associated with the acquisition of companies and the changes in the discount rate and risk margin components of the fair value of liabilities related to our assumed retroactive reinsurance agreements for which we have elected the fair value option. The six months ended June 30, 2022 included accelerated amortization of $96 million corresponding to increased favorable PPD on net ultimate liabilities recorded in our Run-off segment.

| enstargroup.com 8 Consolidated Results by Segment - YTD 2021 Six Months Ended June 30, 2021 Run-off Investment s Legacy Underwriting Corporate & Other (1) Total INCOME Net premiums earned $ 115 $ — $ 37 $ — $ 152 Net investment income — 137 1 — 138 Net realized losses — (4) (1) — (5) Net unrealized gains — 390 — — 390 Other income (expense) 36 — (9) (11) 16 Net gain of sale of subsidiaries — — — 15 15 Total income 151 523 28 4 706 EXPENSES Net incurred losses and loss adjustment expenses Current period 86 — 18 — 104 Prior period (98) — (3) (19) (120) Total net incurred losses and loss adjustment expenses (12) — 15 (19) (16) Acquisition costs 29 — 10 — 39 General and administrative expenses 92 16 3 65 176 Total expenses 109 16 28 46 199 EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 42 507 — (42) 507 Earnings from equity method investments — 115 — — 115 SEGMENT INCOME (LOSS) $ 42 $ 622 $ — (42) 622 Interest expense (33) (33) Net foreign exchange gains 7 7 Income tax expense (3) (3) NET EARNINGS 593 Net earnings attributable to noncontrolling interests (14) (14) NET EARNINGS ATTRIBUTABLE TO ENSTAR 579 Dividends on preferred shares (18) (18) NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (103) $ 561 (1) Other income (expense) for corporate and other activities includes the amortization of fair value adjustments associated with the acquisition of DCo and Morse TEC. Net incurred losses and loss adjustment expenses for corporate and other activities includes amortization of DCAs on retroactive reinsurance contracts and fair value adjustments associated with the acquisition of companies and the changes in the discount rate and risk margin components of the fair value of liabilities related to our assumed retroactive reinsurance agreements for which we have elected the fair value option. The six months ended June 30, 2021 included accelerated amortization of $11 million corresponding to increased favorable PPD on net ultimate liabilities recorded in our Run-off segment.

| enstargroup.com 9 Capital position June 30, 2022 December 31, 2021 $ / pp Change Ordinary shareholders' equity $ 4,183 $ 5,586 $ (1,403) Series D and E preferred shares 510 510 — Total Enstar shareholders' equity 4,693 6,096 (1,403) Noncontrolling interests 193 230 (37) Total shareholders' equity 4,886 6,326 (1,440) Senior notes 991 1,270 (279) Subordinated notes 914 421 493 Total debt obligations 1,905 1,691 214 Redeemable noncontrolling interests 174 179 (5) Total capitalization $ 6,965 $ 8,196 $ (1,231) Total capitalization attributable to Enstar $ 6,598 $ 7,787 $ (1,189) Debt to total capitalization 27.4 % 20.6 % 6.8 pp Debt and Series D and E Preferred Shares to total capitalization 34.7 % 26.9 % 7.8 pp Debt to total capitalization attributable to Enstar 28.9 % 21.7 % 7.2 pp Debt and Series D and E Preferred Shares to total capitalization attributable to Enstar 36.6 % 28.3 % 8.3 pp Capital Position & Credit Ratings Credit ratings (1) Standard and Poor’s Fitch Ratings Long-term issuer BBB (Outlook: Positive) BBB+ (Outlook: Stable) 2029 Senior Notes BBB BBB 2031 Senior Notes BBB- BBB 2040 and 2042 Junior Subordinated Notes BB+ BBB- 2031 Subordinated Notes Not Rated Not Rated Series D and E Preferred Shares BB+ BBB- (1) Credit ratings are provided by third parties, Standard & Poor’s and Fitch Ratings, and are subject to certain limitations and disclaimers. For information on these ratings, refer to the rating agencies’ websites and other publications. pp - Percentage point(s)

| enstargroup.com 10 Non-GAAP Measures Non-GAAP Measure Definition Purpose of Non-GAAP Measure over GAAP Measure Adjusted book value per ordinary share Total Enstar ordinary shareholders' equity Divided by Number of ordinary shares outstanding, adjusted for: -the ultimate effect of any dilutive securities on the number of ordinary shares outstanding Increases the number of ordinary shares to reflect equity awards granted but not yet vested as, over the long term, this presents a prudent view of our book value per share. We use this non-GAAP measure in our incentive compensation program. Adjusted return on equity (%) Adjusted operating income (loss) attributable to Enstar ordinary shareholders divided by adjusted opening Enstar ordinary shareholder's equity Calculating the operating income (loss) as a percentage of our adjusted opening Enstar ordinary shareholders' equity provides a more valuable and consistent measure of the performance of our business, and enhances comparisons to prior periods: • by adjusting investment returns for the temporary impact of the change in fair value of fixed maturity securities (both credit spreads and interest rates) which we hold until the earlier of maturity or used to fund any settlement of related liabilities which are generally recorded at cost; • by removing the impact of non-cash charges that obscure our trends on a consistent basis; and • by removing items that are not indicative of our ongoing operations; We use this non-GAAP measure in our annual incentive compensation program. We include the amortization of fair value adjustments as a non- GAAP adjustment to the adjusted operating income (loss) attributable to Enstar ordinary shareholders as it is considered to be a non-cash charge and not indicative of our operating results. Adjusted operating income (loss) attributable to Enstar ordinary shareholders (numerator) Net earnings (loss) attributable to Enstar ordinary shareholders, adjusted for: -net realized and unrealized (gains) losses on fixed maturity investments and funds held- directly managed -change in fair value of insurance contracts for which we have elected the fair value option (1) -amortization of fair value adjustments -net gain/loss on purchase and sales of subsidiaries (if any) -net earnings from discontinued operations (if any) -tax effects of adjustments -adjustments attributable to noncontrolling interests Adjusted opening Enstar ordinary shareholders' equity (denominator) Opening Enstar ordinary shareholders' equity, less: -net unrealized gains (losses) on fixed maturity investments and funds held-directly managed, -fair value of insurance contracts for which we have elected the fair value option (1), -fair value adjustments, and -net assets of held for sale or disposed subsidiaries classified as discontinued operations (if any) Adjusted total investment return (%) Adjusted total investment return (dollars) recognized in earnings for the applicable period divided by period average adjusted total investable assets. Provides a key measure of the return generated on the capital held in the business and is reflective of our investment strategy. Provides a consistent measure of investment returns as a percentage of all assets generating investment returns. Adjusts investment returns for the temporary impact of the change in fair value of fixed maturity securities (both credit spreads and interest rates) which we hold until the earlier of maturity or used to fund any settlement of related liabilities which are generally recorded at cost. Adjusted total investment return ($) (numerator) Total investment return (dollars), adjusted for: -net realized and unrealized (gains) losses on fixed maturity investments and funds held- directly managed Adjusted average aggregate total investable assets (denominator) Total average investable assets, adjusted for: -net unrealized (gains) losses on fixed maturities, AFS investments included within AOCI -net unrealized (gains) losses on fixed maturities, trading instruments (1) Comprises the discount rate and risk margin components. (1) Comprises the discount rate and risk margin components.

| enstargroup.com 11 Non-GAAP Measures (continued) Non-GAAP Measure Definition Purpose of Non-GAAP Measure over GAAP Measure Adjusted run-off liability earnings (%) Adjusted PPD divided by average adjusted net loss reserves Calculating the RLE as a percentage of our adjusted average net loss reserves provides a more meaningful measurement of our claims management performance. We use this measure to evaluate our ability to settle our obligations for amounts less than our initial estimate at the point of acquiring the obligations. In order to provide a complete and consistent picture of our claims performance, we combine the reduction (increase) in estimates of prior period net ultimate losses relating to our Run-off segment with the amortization of deferred charge assets, both of which are included in net incurred losses and LAE and have an inverse effect on our results. We also include our performance in managing our defendant A&E liabilities, that do not form part of loss reserves. The remaining components of net incurred losses and LAE and net loss reserves are not considered key components of our claims performance as they are either not non-life run-off in nature, or are considered to be non-cash charges that obscure our trends on a consistent basis. We use this measure to assess the performance of our claim strategies and part of the performance assessment of our past acquisitions. Adjusted prior period development (numerator) Prior period net incurred losses and LAE, adjusted to: Remove: -Legacy Underwriting and Enhanzed Re operations -the reduction/(increase) in provisions for unallocated LAE (ULAE) -amortization of fair value adjustments, -change in fair value of insurance contracts for which we have elected the fair value option (1), and Add: -the reduction/(increase) in estimates of our defendant A&E ultimate net liabilities. Adjusted net loss reserves (denominator) Net losses and LAE, adjusted to: Remove: -Legacy Underwriting and Enhanzed Re net loss reserves -current period net loss reserves -the net ULAE provision -net fair value adjustments associated with the acquisition of companies, -the fair value adjustments for contracts for which we have elected the fair value option (1) and Add: -net nominal defendant asbestos and environmental exposures. Investable assets - management's view Investable assets, adjusted to reallocate certain categories of investments based on management's view of the underlying economic exposure of a particular investment. Refer to the reconciliation for further details. Management’s view “looks through” the legal form of an investment and aggregates the classification based upon the underlying economic exposure of each investment, which is consistent with the manner in which management views our investment portfolio composition. (1) Comprises the discount rate and risk margin components.

| enstargroup.com 12 Reconciliation to Adjusted Book Value Per Share As of June 30, 2022 December 31, 2021 Equity (1) Ordinary Shares Per Share Amount Equity (1) Ordinary Shares Per Share Amount Book value per ordinary share $ 4,183 17,008,567 $ 245.93 $ 5,586 17,657,944 $ 316.34 Non-GAAP adjustments: Share-based compensation plans 344,890 315,205 Adjusted book value per ordinary share* $ 4,183 17,353,457 $ 241.05 $ 5,586 17,973,149 $ 310.80 (1) Equity comprises Enstar ordinary shareholders' equity, which is calculated as Enstar shareholders' equity less preferred shares ($510 million), prior to any non-GAAP adjustments. * Non-GAAP financial measure.

| enstargroup.com 13 Reconciliation to Adjusted Return on Equity Three Months Ended June 30, 2022 2021 Net (loss) earnings (1) Opening equity (1) (Adj) ROE Annualized (Adj) ROE Net (loss) earnings (1) Opening equity (1) (Adj) ROE Annualized (Adj) ROE Net (loss) earnings/Opening equity/ROE/Annualized ROE (1) $ (493) $ 5,024 (9.8) % (39.3) % $ 378 $ 6,251 6.0 % 24.2 % Non-GAAP adjustments: Net realized and unrealized losses (gains) on fixed maturity investments and funds held - directly managed / Net unrealized losses (gains) on fixed maturity investments and funds held - directly managed (2) 409 458 (110) (228) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) (48) (201) 17 (109) Amortization of fair value adjustments / Fair value adjustments 5 (104) 6 (125) Tax effects of adjustments (4) 20 4 Adjustments attributable to noncontrolling interests (5) (43) 1 Adjusted operating (loss) income/Adjusted opening equity/Adjusted ROE/Annualized adjusted ROE* $ (150) $ 5,177 (2.9) % (11.6) % $ 296 $ 5,789 5.1 % 20.5 % (1) Net (loss) earnings comprises net (loss) earnings attributable to Enstar ordinary shareholders, prior to any non-GAAP adjustments. Opening equity comprises Enstar ordinary shareholders' equity, which is calculated as opening Enstar shareholders' equity less preferred shares ($510 million), prior to any non-GAAP adjustments. (2) Represents the net realized and unrealized losses (gains) related to fixed maturity securities. Our fixed maturity securities are held directly on our balance sheet and also within the "Funds held - directly managed" balance. (3) Comprises the discount rate and risk margin components. (4) Represents an aggregation of the tax expense or benefit associated with the specific country to which the pre-tax adjustment relates, calculated at the applicable jurisdictional tax rate. (5) Represents the impact of the adjustments on the net earnings (loss) attributable to noncontrolling interests associated with the specific subsidiaries to which the adjustments relate. * Non-GAAP financial measure. Six Months Ended June 30, 2022 2021 Net earnings (1) Opening Equity (1) (Adj) Ratio Annualized (Adj) ROE Net earnings (1) Opening Equity (1) (Adj) Ratio Annualized (Adj) ROE Net (loss) earnings/Opening equity/ROE/Annualized ROE (1) $ (775) $ 5,586 (13.9) % (27.7) % $ 561 $ 6,164 9.1 % 18.2 % Non-GAAP adjustments: Net realized and unrealized losses on fixed maturity investments and funds held - directly managed / Net unrealized gains on fixed maturity investments and funds held - directly managed (2) 743 (89) 96 (560) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) (146) (107) (58) (33) Amortization of fair value adjustments / Fair value adjustments 7 (106) 8 (128) Net gain on sales of subsidiaries — (15) Tax effects of adjustments (4) (4) (13) Adjustments attributable to noncontrolling interests (5) (48) 12 Adjusted operating (loss) income/Adjusted opening equity/Adjusted ROE/Annualized adjusted ROE* $ (223) $ 5,284 (4.2) % (8.4) % $ 591 $ 5,443 10.9 % 21.7 %

| enstargroup.com 14 Reconciliation to Adjusted Run-off Liability Earnings - QTD Three Months Ended As of Three Months Ended June 30, 2022 June 30, 2022 March 31, 2022 June 30, 2022 June 30, 2022 PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % PPD/net loss reserves/Annualized RLE $ 79 $ 12,238 $ 10,962 $ 11,600 2.7 % Non-GAAP Adjustments: Enhanzed Re (1) (147) (150) (149) Legacy Underwriting 6 (140) (142) (141) Net loss reserves - current period — (26) (13) (20) Reduction in provisions for ULAE / Net ULAE provisions (13) (504) (394) (449) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 5 99 104 102 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) (48) 239 201 220 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 1 574 586 580 Adjusted PPD/Adjusted net loss reserves/Annualized Adjusted RLE* $ 29 $ 12,333 $ 11,154 $ 11,743 1.0 % (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure. Three Months Ended As of Three Months Ended June 30, 2021 June 30, 2021 March 31, 2021 June 30, 2021 June 30, 2021 PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % PPD/net loss reserves/Annualized RLE $ 10 $ 10,835 $ 9,215 $ 10,025 0.4 % Non-GAAP Adjustments: Legacy Underwriting 4 (156) (153) (155) Net loss reserves - current period — (91) (48) (70) Reduction in provisions for ULAE / Net ULAE provisions (18) (410) (396) (403) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 6 120 125 123 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 17 91 109 100 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 5 584 599 592 Adjusted PPD/Adjusted net loss reserves/Annualized Adjusted RLE* $ 24 $ 10,973 $ 9,451 $ 10,212 0.9 %

| enstargroup.com 15 Reconciliation to Adjusted Run-off Liability Earnings - YTD Six Months Ended As of Six Months Ended June 30, 2021 June 30, 2021 December 31, 2020 June 30, 2021 June 30, 2021 PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % (in millions of U.S. dollars) PPD/Net loss reserves/RLE $ 120 $ 10,835 $ 8,544 $ 9,690 2.5 % Non-GAAP Adjustments: Legacy Underwriting (2) (156) (955) (556) Increase (reduction) in estimates of net ultimate losses - current period — (91) — (46) Increase (reduction) in provisions for ULAE (32) (410) (334) (372) Amortization of fair value adjustments 8 120 128 124 Changes in fair value - fair value option (1) (58) 91 33 62 Change in estimate of net ultimate liabilities - defendant A&E 14 584 615 600 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE* $ 50 $ 10,973 $ 8,031 $ 9,502 1.1 % (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure. Six Months Ended As of Six Months Ended June 30, 2022 June 30, 2022 December 31, 2021 June 30, 2022 June 30, 2022 PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % (in millions of U.S. dollars) PPD/Net loss reserves/RLE $ 222 $ 12,238 $ 11,555 $ 11,897 3.7 % Non-GAAP Adjustments: Enhanzed Re (29) (147) (181) (164) Legacy Underwriting 5 (140) (153) (147) Increase (reduction) in estimates of net ultimate losses - current period — (26) — (13) Increase (reduction) in provisions for ULAE (35) (504) (416) (460) Amortization of fair value adjustments 7 99 106 103 Changes in fair value - fair value option (1) (146) 239 107 173 Change in estimate of net ultimate liabilities - defendant A&E 4 574 574 574 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE* $ 28 $ 12,333 $ 11,592 $ 11,963 0.5 %

| enstargroup.com 16 Reconciliation to Adjusted Total Investment Return Three Months Ended June 30, Six Months Ended June 30, 2022 2021 2022 2021 Investment results Net investment income $ 106 $ 76 $ 186 $ 138 Net realized (losses) gains (38) 6 (75) (5) Net unrealized (losses) gains (591) 400 (972) 390 Earnings (loss) from equity method investments 1 (3) 32 115 TIR ($) $ (522) $ 479 $ (829) $ 638 Non-GAAP adjustment: Net realized and unrealized losses (gains) on fixed maturity investments and funds held-directly managed 409 (110) 743 96 Adjusted TIR ($)* $ (113) $ 369 $ (86) $ 734 Total investments 15,827 14,621 15,827 14,621 Cash and cash equivalents, including restricted cash and cash equivalents 1,086 1,126 1,086 1,126 Funds held by reinsured companies 3,956 2,202 3,956 2,202 Net variable interest entity assets — 2,220 — 2,220 Total investable assets $ 20,869 $ 20,169 $ 20,869 $ 20,169 Average aggregate invested assets, at fair value (1) $ 19,826 $ 19,176 $ 20,464 $ 18,636 Annualized TIR % (2) (10.5) % 10.0 % (8.1) % 6.8 % Non-GAAP adjustment: Net unrealized losses (gains) on fixed maturities, AFS investments included within AOCI and net unrealized losses (gains) on fixed maturities, trading instruments 1,246 (339) 1,246 (339) Adjusted investable assets* $ 22,115 $ 19,830 $ 22,115 $ 19,830 Adjusted average aggregate invested assets, at fair value (3) $ 20,711 $ 18,896 $ 21,024 $ 18,260 Annualized adjusted TIR %* (4) (2.2) % 7.8 % (0.8) % 8.0 % (1) This amount is a two and three period average of the total investable assets for the three and six ended June 30, 2022 and 2021, respectively, as presented above, and is comprised of amounts disclosed in our quarterly and annual U.S. GAAP consolidated financial statements. (2) Annualized TIR % is calculated by dividing the annualized TIR ($) by average aggregate invested assets, at fair value. (3) This amount is a two and three period average of the adjusted investable assets* for the three and six ended June 30, 2022 and 2021, respectively, as presented above. (4) Annualized adjusted TIR %* is calculated by dividing the annualized adjusted TIR* ($) by adjusted average aggregate invested assets, at fair value*. *Non-GAAP measure.

| enstargroup.com 17 Investable Assets - Management’s View* - June 30, 2022 * Non-GAAP financial measure. Consolidated Balance Sheet View June 30, 2022 Exchange traded funds backed by fixed income securities Bonds, CLO equities and private credit held in equity format Equities, private equity, privately held equity, and real estate held in fund format CLO equity funds Other assets and liabilities in funds held format Private equities in infrastructure format Cash held in fund format June 30, 2022 Management's View of Underlying Economic Exposure Short-term and fixed maturity investments, trading and AFS and funds held - directly managed, excluding other assets $ 10,374 $ 10,374 Fixed maturities Other assets included within funds held - directly managed 46 (46) — Equities 1,776 (562) (117) 86 1,183 Equities* Other Investments: Hedge funds 447 447 Hedge funds Fixed income funds 609 562 58 68 1,297 Bond/loan funds* Equity funds 3 (3) — Private equity funds 1,240 (295) (13) (306) 626 Private equity funds* CLO equities 144 27 213 384 CLO equities* CLO equity funds 213 (213) — Private credit funds 318 32 95 445 Private credit* Real estate debt fund 151 49 200 Real estate* — 13 13 Infrastructure* Total 3,125 3,412 Equity method investments 506 506 Equity method investments Total investments 15,827 15,475 Cash and cash equivalents (including restricted cash) 1,086 306 1,392 Cash and cash equivalents (including restricted cash) Funds held by reinsured companies 3,956 46 4,002 Funds held* Total investable assets $ 20,869 $ 20,869 Total investable assets

| enstargroup.com 18 Investable Assets - Management’s View* - December 31, 2021 * Non-GAAP financial measure. Consolidated Balance Sheet View December 31, 2021 Exchange traded funds backed by fixed income securities Bonds, CLO equities and private debt held in equity format Equities, privately held equity, private credit and real estate held in fund format CLO equity funds Other assets and liabilities in funds held format December 31, 2021 Management's View of Underlying Economic Exposure Short-term and fixed maturity investments, trading and AFS and funds held - directly managed, excluding other assets $ 12,254 $ 12,254 Fixed maturities Other assets included within funds held - directly managed 201 (201) — Equities 1,995 (969) (121) (3) 902 Equities* Other Investments: Hedge funds 291 291 Hedge funds Fixed income funds 573 969 64 1,606 Bond/loan funds* Equity funds 5 (5) — Private equity funds 752 (110) 642 Private equity funds* CLO equities 161 32 207 400 CLO equities* CLO equity funds 207 (207) — Private credit funds 275 25 85 385 Private credit* Real estate debt fund 69 33 102 Real estate* Total 2,333 3,426 Equity method investments 493 493 Equity method investments Total investments 17,276 17,075 Cash and cash equivalents (including restricted cash) 2,092 2,092 Cash and cash equivalents (including restricted cash) Funds held by reinsured companies 2,340 201 2,541 Funds held* Total investable assets $ 21,708 $ 21,708 Total investable assets