#1ENSTAR ENSTAR GROUP LIMITED Company Overview Mid-Year Update August 2021 enstargroup.com#2DISCLAIMER For more complete information about Enstar Group Limited, you should read our reports filed with the SEC. You may get these documents for free through EDGAR on the SEC website at www.sec.gov, or through our website at https://investor.enstargroup.com/sec-filings. IMPORTANT INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information contained in this presentation, may include certain forward-looking statements regarding our views with respect to our business, operations, loss reserves, strategy, investment portfolio, economic model, and our expected performance for future periods, as well as the insurance market and industry conditions. These statements are intended as "forward-looking statements" under the Private Securities Litigation Reform Act of 1995. Actual results may materially differ from those set forth in the forward-looking statements. You may identify forward- looking statements by the use of words such as "believe," "expect," "plan," "intend," "anticipate," "estimate,” “predict,” “potential," "may," "should," "could," "will" or other words or expressions of similar meaning, although not all forward-looking statements contain such terms. Forward-looking statements involve significant risks and uncertainties, including risks of changing and uncertain economic conditions, the success of implementing our business strategies, the adequacy of our loss reserves, ongoing and future regulatory developments disrupting our business, lengthy and unpredictable litigation, risks relating to our acquisitions, increasing competitive pressures, loss of key personnel, risks relating to our active underwriting businesses, the performance of our investment portfolio and liquidity, and other factors detailed in our Annual Report on Form 10-K for the year ended December 31, 2020, our Form 10-Q for the interim period ended June 30, 2021, and our other reports filed from time to time with the Securities and Exchange Commission ("SEC"). Any forward-looking statement you see or hear during the presentation reflects Enstar Group Limited's current views with respect to future events and is subject to these and other risks, uncertainties and assumptions. If any of these risks or uncertainties materialize, or if our underlying assumptions prove to be incorrect, actual results may vary significantly from what we projected. You are cautioned not to place undue reliance on these forward- looking statements, which speak only as of the date on which they are made. The date of this presentation is listed on the cover page and Enstar does not undertake to update or keep it accurate after such date. ADDITIONAL INFORMATION The company has an effective shelf registration statement (including a prospectus) on file with the SEC. Any offering of securities will be made only by means of a prospectus supplement, which will be filed with the SEC. In the event that the company undertakes an offering, you may obtain a copy of the prospectus supplement and accompanying prospectus for the offering by visiting EDGAR on the SEC website at www.sec.gov. ENSTAR Property of Enstar Group Limited - Not for Distribution 2#3A LEADING GLOBAL INSURANCE GROUP Enstar is a leading global insurance group that offers innovative capital release solutions through our network of group companies. We have a 27+ year history of operating in the run-off space, with more than 100 total acquisitive transactions completed to date.#4OUR HISTORY Enstar Group has become a global leader in releasing value for the world's largest insurers and reinsurers 1993 2001 2007 2020 Founded by members of the current management team in Bermuda in 1993 Holding company formed Merged with Enstar to form Enstar Group Limited (ticker:ESGR) Public listing Nasdaq $8.7bn total capital under management 1 ENSTAR CASTLEWOOD CASTLEWOOD ENSTAR ENSTAR 1 Total Capital under management includes includes, Ordinary Equity, Preferred Shares, Redeemable Non- controlling Interest and non- controlling Interest, Public Debt and Bank Debt Property of Enstar Group Limited - Not for Distribution 4#5KEY MILESTONES Executing market-leading solutions to the global (re)insurance market for 27+ years Joint venture with private equity investors created Castlewood Commenced first four Lloyd's RITC transactions through Holdings Limited Became Acquired StarStone "Enstar Shelbourne Group Syndicate 2008 Entered Limited" active underwriting Began trading on NASDAQ Completed reinsurance transaction with QBE and RSA Completed 4 RITC transactions with Am Trust Acquired BorgWarner Morse TEC business; acquired Atrium Completed reinsurance transaction with Coca-Cola Launched Kayla Re with Hillhouse & Stone Point Launched Enhanzed Re with Allianz & Hillhouse Acquired Kayla Re Acquired Maiden Re North America Completed recapitalization of StarStone U.S. Completed first IBT transaction in the US Completed a novation agreement with Lyft Completed reinsurance transaction with Hannover Re, Munich Re, AXA XL and Aspen Completed reinsurance transactions with Coca- Cola, Liberty Mutual, CNA, AXA XL, Hiscox and ProSight Announced reinsurance transaction with RSA 1993 2001 2007 2008 2013 2014 2016 2017 2018 2019 2020 2021 Founded in Bermuda by members of current management team 2001-2010 40 acquisitive transactions ENSTAR 2011-2020 63 acquisitive transactions 100+ acquisitive transactions to date Property of Enstar Group Limited - Not for Distribution 5#6SUMMARY OF RECENT TRANSACTIONS Primary Nature of Business ADC on a diversified mix of commercial and personal insurance lines across the U.K. and Ireland Total Liabilities from Transaction ($millions) 97 2021 RSA (Pending) ProSight LPT of U.S. discontinued workers' compensation and excess workers' compensation lines of business and ADC on a diversified mix of general liability classes of business 500 Hiscox LPT of diversified legacy insurance business, including surplus lines broker business 532 Coca Cola LPT of U.S. workers' compensation liability 48 AXA Group CNA ADC on a diversified mix of global casualty and professional lines LPT of U.S. excess workers' compensation liabilities 1,487 757 Liberty Mutual Hannover Re 2020 LPT of U.S. energy liability, construction liability and homebuilders liability Novation of U.S. asbestos, environmental and workers' compensation liabilities 389 182 Munich Re Business Transfer of Australian public liability, professional liability and builders' warranty liabilities 101 AXA Group LPT of U.S. construction general liability 180 Aspen Lyft ADC on a diversified mix of property, liability and specialty lines of business across the U.S., U.K. and Europe LPT of U.S. motor liabilities 782 465 Total 5,520 ENSTAR Property of Enstar Group Limited - Not for Distribution 6#7TRANSACTION CONSIDERATIONS BESPOKE TRANSACTION CONSIDERATIONS Each M&A transaction analysis is bespoke and deal considerations vary. STRUCTURAL FEATURES INVESTMENT YIELD AND COLLATERAL STRUCTURE ENSTAR EXTERNAL FACTORS CLAIMS SAVINGS CAPITAL ABSORPTION RISK PAYOUT PATTERNS VOLATILITY LIABILITY LIMIT Depending on a given transaction the various multifaceted considerations can carry different weights in determining if a given transaction meets our targeted return thresholds. Property of Enstar Group Limited - Not for Distribution 7#8HISTORIC GROWTH $37.0bn of total assets acquired $ millions Assets Acquired Acquired Total Assets and Gross Reserves By Year Gross Reserves and Defendant A&E liabilities Acquired Completed and Pending Transactions 2011 and 10,394 8,191 48 Prior 2012 411 411 4 2013 3,660 2,635 6 2014 2,547 1,292 2 of gross loss $30.0bn reserves and 2015 2,967 2,357 11 defendant A&E liabilities acquired 2016 1,846 1,627 5 2017 2,110 2,097 6 2018 4,478 3,216 8 2019 3,060 2,772 9 of reserves and 2020 1,710 1,710 5 $16.2bn defendant A&E liabilities have been 2021 3,713 3,628 6 successfully run-off Pending 97 97 1 Total 36,993 30,033 111 ENSTAR Property of Enstar Group Limited - Not for Distribution 8#9NON-LIFE RUN-OFF A large and growing market Global run-off NORTH AMERICA liabilities are $402bn estimated at $864bn Market Drivers UK & CONTINENTAL EUROPE $302bn REST OF WORLD $160bn Solvency II & Prolonged Low Capital Efficiency Interest Rate Environment Reserve Releases Declining Major Cat Loss Brexit Business Transfer Legislation Increased Consolidation ENSTAR Source: Global Insurance Run-Off Survey 2021 performed by PwC, IRLA, and AIRROC. Property of Enstar Group Limited - Not for Distribution 9#10BOOK VALUE AND SHARE PRICE PERFORMANCE $304.59 350% Diluted book value per share 300% June 30, 2021 250% 200% Pro Forma Fully Diluted book 150% $319.25 value per share June 30, 2021 2 100% 14.77% Compound annual 50% Comparison of 10 Year Cumulative Total Return & Growth in Fully Diluted BVPS growth rate in book value per share since 2010 (50)% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 YTD 2021 -Enstar Fully Diluted BVPS - ESGR Share Price (1) S&P 500 (1) S&P Insurance Index (1) Enstar Pro Forma Fully Diluted BVPS (2) (1) Source: S&P Market Intelligence (2) Pro forma fully diluted book value per share is a Non-GAAP measure that reflects adjustments to the numerator and denominator of fully diluted book value per share to give effect to share repurchase transactions completed subsequent to June 30, 2021. Refer to Book Value Per Share on slide 20. ENSTAR Property of Enstar Group Limited - Not for Distribution 10#11FINANCIAL HIGHLIGHTS Key Earnings Metrics $560.5m Net Earnings Six Months Ended June 30, 2021 $13.0bn Total Reserves June 30, 2021 $81.1m $24.6bn Run-off Reserve/Claims Savings¹ Six Months Ended June 30, 2021 $304.59 Diluted Book Value Per Share June 30, 2021 Total Assets June 30, 2021 2.30% Annualized Investment Book Yield Six Months Ended June 30, 2021 ENSTAR 16.0% Debt to Capital Ratio 2 June 30, 2021 'AAA' Capital Redundancy at S&P³ 1 Reserve / Claims Savings is a non-GAAP measure used by management to evaluate claims management performance in our Run-Off Segment. Refer to the explanatory note on slide 19 2 Total capital attributable to Enstar includes Enstar shareholders' equity and debt obligations and excludes noncontrolling interest and redeemable noncontrolling interest 3 Source: Standard & Poor's, Enstar Group Ltd. Full Analysis, 11/03/2020 Property of Enstar Group Limited - Not for Distribution 11#12ECONOMIC MODEL Our Run-off Business Enstar recycles capital through our business operating cycle, creating a strong source of book value per share growth and internal financing Acquire Liabilities Acquire insurance liabilities from motivated insurers Leverage experience and industry relationships • Global footprint aids in sourcing transactions Maintain price discipline Manage Liabilities Strive to generate profits from run- off entities through loss reserve savings, operational efficiencies, and investment income • Manage claims professionally, expeditiously and cost effectively Settle faster than the original claims payment pattern, thereby incurring lower ultimate claims handling costs ENSTAR Redeploy Capital Profits released from the underlying regulated entities can be redeployed into the business to fund future acquisitions and/or repay financing • Profitably commute assumed liabilities and ceded reinsurance assets Property of Enstar Group Limited - Not for Distribution 12#13STRATEGIC TRANSACTIONS Completed Internal Reorganization of StarStone and Atrium in early 2021 Recapitalization of StarStone US Closed Q4 2020 Atrium Exchange Transaction Closed Q1 2021 Sale of StarStone Underwriting Ltd Closed Q1 2021 StarStone International Put into Runoff StarStone US received new equity investments from an experienced investor group, bringing equity capitalization to over $900m Led by Jeff Consolino, incoming CEO, and Ed Noonan, incoming Executive Chairman Rebranded as Core Specialty Enstar acquired all of the Stone Point funds' interest in the new Core Specialty in exchange for a majority of Enstar's interest in Atrium Enstar and Stone Point sold SUL, the Lloyd's managing agency, together with the right to operate Lloyd's Syndicate 1301, to Inigo Limited, a new specialty re/insurance company. Retained interest in go-forward "Inigo" Operations will remain in place to serve the needs of policyholders/regulatory requirements Enstar will no longer consolidate any active underwriting operations in financial statements on a net basis, but retains exposure to active platforms through minority investments 13#14INVESTMENT PORTFOLIO COMPOSITION $20.2bn Total Investable Assets 1 $1.1bn Cash and restricted cash $13.7bn 4.69yrs Investment Portfolio 2 Average Duration 3 A+ Average Investment Portfolio Credit Rating 4 Investable Assets (As of June 30, 2021) - Composition by Asset Class5 2.3% Book Yield Six Months Ended June 30, 2021 Cash and Cash Equivalents 5.6% Fixed Maturities 53.1% Other Fixed Income 6 Equities? Other Investments Funds Held 8 4.2% 10.4% 4.8% 10.9% Net Variable Interest Entity Assets of the In Re Fund 11.0% Other Investments Fixed Income, Trading and AFS Other Fixed Income Private equity funds 2.7% U.S. Government & Agency 3.9 % Fixed Income Funds 3.0 % Hedge funds 0.4 % U.K. Government 0.2% Other Government 2.4 % Private Credit Funds Total 1.2% Equity funds - % CLO equities 0.7 % 4.2 % CLO equity funds 0.9% Corporate 33.0 % Other 0.1 % Municipal 1.2% Equities Total 4.8 % Publicly traded equities 1.5 % Residential Mortgage-backed 2.9% Exchange-traded funds 2.5% Commercial Mortgage-backed 4.9 % Privately held equities 1.7 % Asset-backed 4.6 % Total 53.1 % Equity method investments Total 4.7 % 10.4 % 1. Includes total investments, cash and cash equivalents (including restricted cash), funds held by reinsured companies and the net variable interest entity assets of InRe Fund. 2. Fair Value as of June 30, 2021. 3. Duration calculation includes cash and cash equivalents, short-term investments, fixed maturities and the fixed maturities within our funds held - directly managed portfolios at June 30, 2021. 4. The average credit ratings calculation includes cash and cash equivalents, short-term investments, fixed maturities and the fixed maturities within our funds held - directly managed portfolios at June 30, 2021 5. See Appendix for further detail on investable asset composition. 6. Classified as "Other Investments" under GAAP 7. Includes publicly traded equities, exchange-traded funds, privately held equities, and equity method investments. 8. Includes Funds held by reinsured companies and assets within funds held - directly managed. 14 14#15CAPITAL, LIQUIDITY & LEVERAGE Debt/total 16.0% $1,300 capital ratio 1 June 30, 2021 21.9% $1,100 Enstar Group Debt / Capital Ratio $1,500 35.0% 20.5% Debt + $900 19.2% preferred/total capital ratio 1 June 30, 2021 $700 $500 S&P (BBB) positive Long-term issuer outlook $300 6.5% investment grade credit Fitch (BBB) ratings $100 positive $107 outlook ENSTAR enstargroup.com $452 $320 2.2% $600 19.4% 17.1% $862 18.1% 19.7% $674 $647 $1,191 $1,373 $1,364 30.0% 25.0% 20.0% 17.1% 16.0% 15.0% 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 $-100 0.0% Total Debt mns Debt/(Debt + Shareholders' Equity) 1 Total capital attributable to Enstar includes Enstar Group Limited shareholders' equity and debt obligations and excludes noncontrolling interest and redeemable noncontrolling interest. Property of Enstar Group Limited = Not for Distribution 15 5.0% 10.0%#16APPENDIX ENSTAR Property of Enstar Group Limited - Not for Distribution 16#17FINANCIAL DATA Summary Income Statement $ millions Net premiums earned Fees & commission income Net investment income and net realized and unrealized gains Other income Net gain on sale of subsidiaries Net incurred losses and LAE liabilities Acquisition costs Interest expense General and administrative and net foreign exchange Income taxes Earnings (losses) from equity method investments Net earnings from continuing operations Net loss from discontinuing operations, net of income tax expense Net earnings Net (earnings) loss attributable to non-controlling interest Dividends on preferred shares Net earnings attributable to Enstar Group Limited ENSTAR 3 Months Ended June 30, 2021 3 Months Ended June 30, 2020 $143 6 Months Ended June 30, 2021 6 Months Ended June 30, 2020 $60 8 481 $153 $302 10 18 18 1,062 523 508 (1) (3) 19 — - 15 (39) (5 (187) 16 (230) (49) (39) (95) (16) (14) (32) (27) (85) (149) (170) (238) (9) (17) (3) (11) (3) (9) 115 4 389 789 593 250 - (1) (3) 389 788 593 247 20 (14) 53 (9) (9) (18) (18) $377 $799 $561 $282 Property of Enstar Group Limited - Not for Distribution 17 12#18FINANCIAL DATA Summary Balance Sheet $ millions Assets Total investments Cash and cash equivalents (including restricted cash) Funds held by reinsured companies Variable interest entity assets of the InRe Fund Reinsurance and insurance recoverable Other Total Assets Liabilities Loss and loss adjustment expense June 30, 2021 December 31, 2020 $14,622 $15,257 1,126 1,373 2,202 636 2,220 1,977 2,089 2,474 2,292 24,621 21,647 13,038 10,593 Defendant asbestos and environmental liabilities 678 706 Debt obligations 1,364 1,373 Variable interest entity liabilities of the InRe Fund 694 Other 1,470 1,922 Total Liabilities 17,244 14,594 Redeemable noncontrolling interest ("RNCI") Shareholders' Equity Ordinary shareholders' equity Series D & E preferred shares Non-controlling interest Total Shareholders' Equity Total Liabilities, RNCI & Shareholders' Equity ENSTAR 177 365 6,677 510 6,164 510 13 14 7,200 $24,621 6,688 $21,647 Property of Enstar Group Limited - Not for Distribution 18#19RUN-OFF RESERVE / CLAIMS SAVINGS Reconciliation of reserve / claims savings to GAAP line items in the Run- off segment: FS Reference (1) Three Months Ended June 30, 2021 2020 Six Months Ended June 30, 2021 2020 Net incurred losses and LAE: Reduction (increase) in estimates of net ultimate losses - prior periods (A) Reduction (increase) in estimates of net ultimate losses - current period Reduction in provisions for unallocated LAE Note 8 $41,696 $55,910 $67,063 $83,473 Note 8 (40,445) (8,086) (83,135) (15,935) Note 8 15,746 12,425 28,444 19,904 Net incurred losses and LAE - Run-off Note 8 $16,997 $60,249 $12,372 $87,442 Other income (expense): Reduction in estimates of ultimate net defendant A&E liabilities - prior periods (B) Reduction (increase) in estimated future defendant A&E expenses Note 9 $4,450 $ Note 9 745 1,978 975 $14,002 $26,893 3,508 3,003 All other income (expense) - Run-off Other income (expense) - Run-off 1 (2,054) 1 (1,234) Note 22 $5,196 $899 $17,511 $28,662 Run-off reserve / claims savings: Reduction (increase) in estimates of net ultimate losses - prior periods = (A) Reduction in estimates of ultimate net defendant A&E liabilities - prior periods = (B) Reserve / claims savings: total reduction in net ultimate losses (2) = (A) + (B) Note 8 Note 9 $41,696 4,450 $55,910 $67,063 $83,473 $46,146 1,978 $57,888 14,002 26,893 $81,065 $110,366 (1) Refer to the corresponding note to our consolidated financial statements included within Item 1 of our Quarterly Report on Form 10-Q for the interim period ended June 30, 2021 for further details. (2) Reserve / Claims Savings is a non-GAAP measure calculated using components of amounts determined in accordance with U.S. GAAP and disclosed in our quarterly and annual U.S. GAAP consolidated financial statements. Reserve / Claims Savings is calculated by adding (i) the reduction (increase) in estimates of net ultimate losses relating to prior periods, included in net incurred losses and LAE, and (ii) the reduction (increase) in estimates of ultimate net defendant asbestos and environmental ("Defendant A&E") liabilities relating to prior periods, included in other income (expense). Because the reduction (increase) in estimates of ultimate Defendant A&E liabilities for prior periods is presented as a component of other income (expense) in our consolidated statement of earnings, there is not a U.S. GAAP measure that is directly comparable to Reserve/Claims Savings presented on a non-GAAP basis. However, we believe Reserve / Claims Savings provides investors with a meaningful measure of claims management performance within our Claims Management segment that is consistent with management's view of the business because it combines the reduction (increase) in estimates of net ultimate losses related to our direct exposure to certain acquired asbestos and environmental liabilities with the reduction (increase) in estimates of net ultimate losses related to liabilities that we have insured. ENSTAR Property of Enstar Group Limited - Not for Distribution 19#20BOOK VALUE PER SHARE June 30, 2021 December 31, 2020 Numerator: Total Enstar shareholders' equity Less: Series D and E preferred shares Total Enstar ordinary shareholders' equity (A) Proceeds from assumed conversion of warrants (1) $7,187,308 510,000 6,677,308 $6,674,395 510,000 6,164,395 20,229 Numerator for fully diluted book value per ordinary share calculations (B) $6,677,308 $6,184,624 July Share Repurchases (2) (890,023) Numerator for pro forma fully diluted book value per ordinary share calculations (C) 5,787,285 Denominator: Ordinary shares outstanding (D) (3) 21,604,803 21,519,602 Effect of dilutive securities: Share-based compensation plans (4) Warrants (1) Fully diluted ordinary shares outstanding (E) July Share Repurchases (2) Pro forma fully diluted ordinary shares outstanding (F) Book value per ordinary share: 317,380 298,095 21,922,183 175,901 21,993,598 Basic book value per ordinary share = (A)/(D) Fully diluted book value per ordinary share = (B)/(E) (3,794,711) 18,127,472 $309.07 $304.59 $319.25 $286.45 $281.20 Pro forma fully diluted book value per ordinary share = (C) / (F) (1) Warrants to acquire 175,901 Series C Non-Voting Ordinary Shares for an exercise price of $115.00 per share were exercised on a non-cash basis during the six months ended June 30, 2021, which resulted in a total of 89,590 Series C Non-Voting Ordinary Shares being issued in the period. (2) Represents shares repurchased in transactions described within the explanatory notes below. (3) Ordinary shares outstanding includes voting and non-voting shares but excludes ordinary shares held in the Enstar Group Limited Employee Benefit Trust (the "EB Trust") in respect of awards made under our Joint Share Ownership Plan, a sub-plan to our Amended and Restated 2016 Equity Incentive Plan (the "JSOP"). (4) Share-based dilutive securities include restricted shares, restricted share units, and performance share units ("PSUs"). The amounts for PSUs, and for ordinary shares held in the EB Trust in respect of the JSOP, are adjusted at the end of each period end to reflect the latest estimated performance multipliers for the respective awards. The JSOP shares did not have a dilutive effect as at June 30, 2021. Pro Forma Fully Diluted Book Value Per Ordinary Share - Non-GAAP In addition to presenting fully diluted book value per ordinary share calculated as of June 30, 2021, we have presented pro forma fully diluted book value per share, which reflects adjustments to fully diluted book value per share as of June 30, 2021 to give effect to share repurchases that were completed subsequent to June 30, 2021. On July 22, 2021, we completed a repurchase of 3,749,400 of our ordinary shares held by funds managed by Hillhouse Group for a price of $234.52 per share, totaling $879.3 million in aggregate. The shares represented these funds' entire interest in Enstar, which constituted 16.9% of total ordinary shares and 9.4% of voting ordinary shares. Subsequent to June 30, 2021, we have also repurchased 45,311 shares for $10.7 million as part of our ordinary share Repurchase Program before terminating the Repurchase Program on July 15, 2021. We believe that the presentation of pro forma fully diluted book value per share to give effect to these transactions provides readers of our financial statements with useful information regarding the impact of this significant strategic share repurchase that had a material impact on the number of our outstanding ordinary shares. We do not expect to present this measure in future periods. Pro forma fully diluted book value per share is calculated by adjusting the numerator and denominator of fully diluted book value per share to give effect to the completed share repurchase transactions described above. ENSTAR Property of Enstar Group Limited - Not for Distribution 20#21EXECUTIVE MANAGEMENT TEAM Dominic Silvester Chief Executive Officer & Co-founder Years at Enstar: 27 Industry Experience: 30+ years Age: 61 Paul O'Shea President, Co-founder Years at Enstar: 26 Industry Experience: 30+ years Age: 63 Orla Gregory Chief Operating Officer & Acting Chief Financial Officer Years at Enstar: 17 Industry Experience: 25+ years Age: 47 Paul Brockman Chief Claims Officer Years at Enstar: 8 Industry Experience: 25+ years Age: 49 Nazar Alobaidat Chief Investment Officer Years at Enstar: 5 Industry Experience: 20+ years Age: 43 Audrey Taranto General Counsel Years at Enstar: 9 Industry Experience: 10+ years Age: 41 Average Industry Experience: 23+ years Collective Industry Experience: 140+ years Average Years at Enstar: 15+ years ENSTAR Property of Enstar Group Limited - Not for Distribution 21 24#22BOARD OF DIRECTORS Robert Campbell Independent Chairman of the Board Partner, Beck Mack & Oliver US resident; US citizen Financial, accounting and investment expertise, leadership skills Age: 72 Dominic Silvester Enstar Chief Executive Officer; Co-Founder UK resident; UK citizen Company leader, proven ability to manage and grow the business, Industry expertise, corporate strategy Age: 61 Rick Becker Independent Chairman of Compensation and Nominating / Governance Committees Chairman and Founder, Clarity Group, Inc. US resident; US citizen Compensation, industry, and risk management expertise Age: 75 Jim Carey Managing Director, Stone Point Capital LLC US resident; US citizen Investment expertise, significant acquisition experience within the industry, industry knowledge Age: 54 Susan Cross Independent Director Former Executive Vice President and Global Chief Actuary, XL Group Ltd. (now AXA XL) US resident; US citizen Actuarial and analytics expertise, proven insurance and risk executive Age: 61 Hans-Peter Gerhardt Independent Director Former CEO, Asia Capital Re/ Former CEO, PARIS RE Swiss resident; German citizen Underwriting expertise, proven industry veteran, CEO experience Age: 66 Myron Henry Independent Director Former Executive VP & Chief Platform Officer, XL Catlin US resident; US citizen Operations and technology expertise Age: 72 Paul O'Shea Enstar President; Co-Founder Bermuda resident; Dual Bermuda / Irish citizen Company leader, significant track record of successful acquisitions, industry expertise Age: 63 Hitesh Patel Independent Director Former Chief Executive Officer, Lucida plc (UK life insurer); Former KPMG Lead Partner of Regulatory and Insurance UK resident; UK citizen Accounting expertise, significant regulatory and governance skills Age: 60 Poul Winslow Independent Director Head of Thematic Investing, CPPIB Canadian resident; Danish citizen Investment expertise Age: 55 ENSTAR Property of Enstar Group Limited - Not for Distribution 22 22#23MAJOR SHAREHOLDERS Firm or Individual Name CPP Investment Board Stone Point Capital The Vanguard Group Wellington Management BlackRock Institutional Trust Beck, Mack & Oliver LLC Fidelity Management & Research Capital World Investors Dominic Silvester Other Shareholders (< 2.5% economic / < 3.0% voting) Total outstanding August 5, 2021 Economic Percent (1) Voting Percent (1) 21% 8% 9% 9% 6% 6% 6% 6% 5% 5% 4% 4% 4% 4% 3% 3% 3% 3% 39% 52% 100% 100% (1) Percentages are calculated using Enstar's ordinary shares outstanding as of August 5, 2021 and the most recent publicly available information with respect to amounts held by shareholders, which may not reflect current actual shareholder ownership. ENSTAR Property of Enstar Group Limited - Not for Distribution 23 23