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UNITED STATES SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 10-Q

QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the quarterly period ended September 30, 2023

Commission File Number 001-33289

ENSTAR GROUP LIMITED

(Exact name of Registrant as specified in its charter)

BERMUDA			N/A
(State or other jurisdiction of incorporation or organization)			(I.R.S. Employer Identification No.)

Windsor Place, 3rd Floor, 22 Queen Street, Hamilton HM JX, Bermuda

(Address of principal executive offices, including zip code)

Registrant’s telephone number, including area code: (441) 292-3645

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

Title of Each Class			Trading Symbol(s)			Name of Each Exchange on Which Registered
Ordinary shares, par value $1.00 per share			ESGR			The NASDAQ Stock Market			LLC
Depositary Shares, Each Representing a 1/1,000th Interest in a 7.00%			ESGRP			The NASDAQ Stock Market			LLC
Fixed-to-Floating Rate Perpetual Non-Cumulative Preferred Share, Series D, Par Value $1.00 Per Share
Depositary Shares, Each Representing a 1/1,000th Interest in a 7.00%			ESGRO			The NASDAQ Stock Market			LLC
Perpetual Non-Cumulative Preferred Share, Series E, Par Value $1.00 Per Share

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

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

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

Large accelerated filer

☒

Accelerated filer

¨

Non-accelerated filer

¨

Smaller reporting company

☐

Emerging growth company

☐

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

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

As at November 6, 2023, the registrant had outstanding 16,039,324 voting ordinary shares, par value $1.00 per share.

1

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Table of Contents

Enstar Group Limited

Quarterly Report on Form 10-Q

For the Period Ended September 30, 2023

Table of Contents

 

						Page
			Glossary of Key Terms			3
PART I
Item 2.			Management's Discussion and Analysis of Financial Condition and Results of Operations			8
Item 3.			Quantitative and Qualitative Disclosures about Market Risk			60
Item 1.			Financial Statements			61
Item 4.			Controls and Procedures			111
PART II
Item 1.			Legal Proceedings			112
Item 1A.			Risk Factors			112
Item 2.			Unregistered Sales of Equity Securities and Use of Proceeds			112
Item 3.			Defaults Upon Senior Securities			112
Item 4.			Mine Safety Disclosures			112
Item 5.			Other Information			112
Item 6.			Exhibits			113

2

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Table of Contents

GLOSSARY OF KEY TERMS

A&E						Asbestos and environmental
Acquisition costs						Costs that are directly related to the successful efforts of acquiring new insurance contracts or renewing existing insurance contracts, and which principally consist of incremental costs such as: commissions, brokerage expenses, premium taxes and other fees incurred at the time that a contract or policy is issued.
ADC						Adverse development cover – A retrospective reinsurance arrangement that will insure losses in excess of an established reserve and provide protection up to a contractually agreed amount.
Adjusted BVPS						Adjusted book value per ordinary share - Non-GAAP financial measure calculated by dividing Enstar ordinary shareholders’ equity by the number of ordinary shares outstanding, adjusted for equity awards granted and not yet vested. See “Non-GAAP Financial Measures” for reconciliation.
Adjusted RLE						Adjusted run-off liability earnings - Non-GAAP financial measure calculated by dividing adjusted prior period development by average adjusted net loss reserves. See “Non-GAAP Financial Measures” for reconciliation.
Adjusted ROE						Adjusted return on equity - Non-GAAP financial measure calculated by dividing adjusted operating income (loss) attributable to Enstar ordinary shareholders by adjusted opening Enstar ordinary shareholders’ equity. See “Non-GAAP Financial Measures” for reconciliation.
Adjusted TIR						Adjusted total investment return - Non-GAAP financial measure calculated by dividing adjusted total investment return by average adjusted total investable assets. See “Non-GAAP Financial Measures” for reconciliation.
AFS						Available-for-sale
Allianz						Allianz SE
AmTrust						AmTrust Financial Services, Inc.
Annualized						Calculation of the quarterly result or year-to-date result multiplied by four and then divided by the number of quarters elapsed within the applicable year-to-date period.
AOCI						Accumulated other comprehensive income
ASC						Accounting Standards Codification
ASU						Accounting Standards Update
Arden						Arden Reinsurance Company Ltd.
Atrium						Atrium Underwriting Group Limited
bps						Basis point(s)
BMA						Bermuda Monetary Authority
BSCR						Bermuda Solvency Capital Requirement
BVPS						Book value per ordinary share - GAAP financial measure calculated by dividing Enstar ordinary shareholders’ equity by the number of ordinary shares outstanding.
Cavello						Cavello Bay Reinsurance Limited, a wholly-owned subsidiary
Citco						Citco III Limited
CLO						Collateralized loan obligation
Core Specialty						Core Specialty Insurance Holdings, Inc.
DCo						DCo LLC
Defendant A&E liabilities						Defendant asbestos and environmental liabilities - Non-insurance liabilities relating to amounts for indemnity and defense costs for pending and future claims, as well as amounts for environmental liabilities associated with properties.
DCA						Deferred charge asset - The amount by which estimated ultimate losses payable exceed the consideration received at the inception of a retroactive reinsurance agreement and that are subsequently amortized over the estimated loss settlement period.
DGL						Deferred gain liability - The amount by which consideration received exceeds estimated ultimate losses payable at the inception of a retroactive reinsurance agreement and that are subsequently amortized over the estimated loss settlement period.
EB Trust						Enstar Group Limited Employee Benefit Trust

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Table of Contents

GLOSSARY OF KEY TERMS

Enhanzed Re						Enhanzed Reinsurance Ltd.
Enstar						Enstar Group Limited and its consolidated subsidiaries
Enstar Finance						Enstar Finance LLC
Exchange Transaction						The exchange of a portion of our indirect interest in Northshore for all of the Trident V Funds’ indirect interest in StarStone U.S.
FAL						Funds at Lloyd's - A deposit in the form of cash, securities, letters of credit or other approved capital instrument that satisfies the capital requirement to support the Lloyd's syndicate underwriting capacity.
Funds held						The account created with premium due to the reinsurer pursuant to the reinsurance agreement, the balance of which is credited with investment income and losses paid are deducted.
Funds held by reinsured companies						Funds held, as described above, where we receive a fixed crediting rate of return or other contractually agreed return on the assets held.
Funds held - directly managed						Funds held, as described above, where we receive the actual investment portfolio return on the assets held.
Future policyholder benefits						The liability relating to life reinsurance contracts, which are based on the present value of anticipated future cash flows and mortality rates.
Gate or side-pocket						A gate is the ability to deny or delay a redemption request, whereas a side-pocket is a designated account for which the investor loses its redemption rights.
IBNR						Incurred but not reported - The estimated liability for unreported claims that have been incurred, as well as estimates for the possibility that reported claims may settle for amounts that differ from the established case reserves as well as the potential for closed claims to re-open.
Investable assets						The sum of total investments, cash and cash equivalents, restricted cash and cash equivalents and funds held
JSOP						Joint Share Ownership Plan
LAE						Loss adjustment expenses
Lloyd's						This term may refer to either the society of individual and corporate underwriting members that pool and spread risks as members of one or more syndicates, or the Corporation of Lloyd’s, which regulates and provides support services to the Lloyd’s market
LOC						Letters of credit
LPT						Loss Portfolio Transfer - Retroactive reinsurance transaction in which loss obligations that are already incurred are ceded to a reinsurer, subject to any stipulated limits
Monument Re						Monument Insurance Group Limited
Morse TEC						Morse TEC LLC
NAV						Net asset value
NCI						Noncontrolling interests
New business						Material transactions, which generally take the form of reinsurance or direct business transfers, or business acquisitions.
Northshore						Northshore Holdings Limited
OLR						Outstanding loss reserves - Provisions for claims that have been reported and accrued but are unpaid at the balance sheet date.
Parent Company						Enstar Group Limited, excluding its consolidated subsidiaries
pp						Percentage point(s)
PPD						Prior period development - Changes to loss estimates recognized in the current calendar year that relate to loss reserves established in previous calendar years.
Private equity funds						Investments in limited partnerships and limited liability companies
QBE						QBE Insurance Group Limited
QTD						Quarter-to-date
RACQ						RACQ Insurance Limited
Reinsurance to close (RITC)						A business transaction to transfer estimated future liabilities attached to a given year of account of a Lloyd's syndicate into a later year of account of either the same or different Lloyd's syndicate in return for a premium.

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GLOSSARY OF KEY TERMS

Reserves for losses and LAE						Management's best estimate of the ultimate cost of settling losses as of the balance sheet date. This includes OLR and IBNR.
Retroactive reinsurance						Contracts that provide indemnification for losses and LAE with respect to past loss events.
RLE						Run-off liability earnings – GAAP-based financial measure calculated by dividing prior period development by average net loss reserves.
RNCI						Redeemable noncontrolling interests
ROE						Return on equity - GAAP-based financial measure calculated by dividing net earnings (loss) attributable to Enstar ordinary shareholders by opening Enstar ordinary shareholders’ equity
Run-off						A line of business that has been classified as discontinued by the insurer that initially underwrote the given risk
Run-off portfolio						A group of insurance policies classified as run-off.
SEC						U.S. Securities and Exchange Commission
SGL No. 1						SGL No. 1 Limited
StarStone International						StarStone's non-U.S. operations
StarStone U.S.						StarStone U.S. Holdings, Inc. and its subsidiaries
Stone Point						Stone Point Capital LLC
TIR						Total investment return - GAAP financial measure calculated by dividing total investment return, including other comprehensive income, for the applicable period by average total investable assets
Trident V Funds						Trident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P.
U.S. GAAP						Accounting principles generally accepted in the United States of America
ULAE						Unallocated loss adjustment expenses - Loss adjustment expenses relating to run-off costs for the estimated payout of the run-off, such as internal claim management or associated operational support costs.
Unearned premium						The unexpired portion of policy premiums that will be earned over the remaining term of the insurance contract.
VIE						Variable interest entities
YTD						Year-to-date
2021 Repurchase Program						An ordinary share repurchase program adopted by our Board of Directors on November 29, 2021, for the purpose of repurchasing a limited number of our ordinary shares, not to exceed $100 million in aggregate. This plan was fully utilized in April 2022.
2022 Repurchase Program						An ordinary share repurchase program authorized by our Board of Directors on May 5, 2022, which was originally effective through May 5, 2023 and authorized the repurchase of a limited number of our ordinary shares, not to exceed $200 million in aggregate. On February 23, 2023, our Board of Directors authorized the repurchase of an additional $105 million of our ordinary shares, and extended the effective date through February 23, 2024. This program was terminated on March 23, 2023.

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CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

This quarterly report and the documents incorporated by reference herein contain statements that constitute "forward-looking statements" within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended, or the Exchange Act, with respect to our financial condition, results of operations, business strategies, operating efficiencies, competitive positions, growth opportunities, plans and objectives of our management, as well as the markets for our securities and the insurance and reinsurance sectors in general.

Statements that include words such as "estimate," "project," "plan," "intend," "expect," "anticipate," "believe," "would," "should," "could," "seek," "may" and similar statements of a future or forward-looking nature identify forward-looking statements for purposes of the federal securities laws or otherwise.

All forward-looking statements are necessarily estimates or expectations, and not statements of historical fact, reflecting the best judgment of our management and involve a number of risks and uncertainties that could cause actual results to differ materially from those suggested by the forward-looking statements.

These forward looking statements should, therefore, be considered in light of various important factors, including those set forth in this report and in our Annual Report on Form 10-K for the year ended December 31, 2022, which could cause actual results to differ materially from those suggested by the forward-looking statements. These factors include:

•the adequacy of our loss reserves and the need to adjust such reserves as claims develop over time, including due to the impact of emerging claim and coverage issues and disputes that could impact reserve adequacy;

•our acquisitions, including our ability to evaluate opportunities, successfully price acquisitions, address operational challenges, support our planned growth and assimilate acquired portfolios and companies into our internal control system in order to maintain effective internal controls, provide reliable financial reports and prevent fraud;

•increased competitive pressures, including increased competition in the market for acquisitions of run-off business;

•our ability to obtain regulatory approvals, including the timing, terms and conditions of any such approvals, and to satisfy other closing conditions in connection with our acquisition agreements, which could affect our ability to complete acquisitions;

•the variability of statutory capital requirements and the risk that we may require additional capital in the future, which may not be available or may be available only on unfavorable terms;

•our reinsurance subsidiaries may not be able to provide the required collateral to ceding companies pursuant to their reinsurance contracts, including through the use of letters of credit;

•the availability and collectability of our ceded reinsurance;

•the ability of our subsidiaries to distribute funds to us and the resulting impact on our liquidity;

•losses due to foreign currency exchange rate fluctuations;

•climate change and its potential impact on the returns from our run-off business and our investments;

•the value of our investment portfolios and the investment income that we receive from these portfolios may decline materially as a result of market fluctuations and economic conditions, including those related to interest rates, credit spreads and equity prices (including the risk that we may realize losses related to declines in the value of our investments portfolios if we elect to, or are required to, sell investments with unrealized losses);

•the effects of inflation, including its impact on our loss cost trends and operating expenses, and the effects of global economic policy responses to inflation, such as increasing interest rates and their impact on our investment portfolio;

•our ability to structure our investments in a manner that recognizes our liquidity needs;

•our strategic investments in alternative asset classes and joint ventures, which are illiquid and may be volatile;

•our ability to accurately value our investments, which requires methodologies, estimates and assumptions that can be highly subjective, and the inaccuracy of which could adversely affect our financial condition;

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CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

•the complex regulatory environment in which we operate, including that ongoing or future industry regulatory developments will disrupt our business, affect the ability of our subsidiaries to operate in the ordinary course or to make distributions to us, or mandate changes in industry practices in ways that increase our costs, decrease our revenues or require us to alter aspects of the way we do business;

•loss of key personnel;

•operational risks, including cybersecurity events, external hazards, human failures or other difficulties with our information technology systems that could disrupt our business or result in the loss of critical and confidential information, increased costs;

•tax, regulatory or legal restrictions or limitations applicable to us or the (re)insurance business generally;

•changes in tax laws or regulations applicable to us or our subsidiaries, or the risk that we or one of our non-U.S. subsidiaries become subject to significant, or significantly increased, income taxes in the United States or elsewhere; and

•the ownership of our shares resulting from certain provisions of our bye-laws and our status as a Bermuda company.

The factors listed above should not be construed as exhaustive and should be read in conjunction with the Risk Factors that are included in our Annual Report on Form 10-K for the year ended December 31, 2022. We undertake no obligation to publicly update or review any forward looking statement, whether to reflect any change in our expectations with regard thereto, or as a result of new information, future developments or otherwise, except as required by law.

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PART I — FINANCIAL INFORMATION

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

Unless the context indicates otherwise, the terms "Enstar," "we," "us" or "our" mean Enstar Group Limited and its consolidated subsidiaries.

The following discussion and analysis of our financial condition as of September 30, 2023 and our results of operations for the three and nine months ended September 30, 2023 and 2022 should be read in conjunction with our unaudited condensed consolidated financial statements and the related notes included elsewhere in this quarterly report and the audited consolidated financial statements and notes thereto contained in our Annual Report on Form 10-K for the year ended December 31, 2022.

Some of the information contained in this discussion and analysis or included elsewhere in this quarterly report, including information with respect to our plans and strategy for our business, includes forward-looking statements that involve risks, uncertainties and assumptions. Our actual results and the timing of events could differ materially from those anticipated by these forward-looking statements as a result of many factors, including those discussed under "Cautionary Statement Regarding Forward-Looking Statements" and Item 1A of our Annual Report on Form 10-K for the year ended December 31, 2022.

Table of Contents

Section						Page
Operational Highlights						9
Consolidated Results of Operations — for the Three and Nine Months Ended September 30, 2023 and 2022						11
•Overall Measures of Performance						16
•Underwriting Results						17
•Investment Results						23
•General and Administrative Expenses						28
Non-GAAP Financial Measures						29
Other Financial Measures						38
Results of Operations by Segment — for the Three and Nine Months Ended September 30, 2023 and 2022						40
•Run-off Segment						40
•Assumed Life Segment						42
•Investments Segment						44
•Legacy Underwriting Segment						48
Corporate and Other						49
Current Outlook						51
Liquidity and Capital Resources						53

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 8

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Item 2 | Management's Discussion and Analysis | Operational Highlights

Operational Highlights

Our consolidated results reflect our ongoing provision of capital release solutions to our clients by acquiring and managing seasoned liabilities relating to both their continuing and discontinued portfolios.

Operational highlights for the nine months ended September 30, 2023 include:

Transactions

•In April 2023, certain of our wholly-owned subsidiaries completed a LPT agreement with certain subsidiaries of QBE Insurance Group Limited (“QBE”), relating to a diversified portfolio of business underwritten between 2010 and 2020. Upon closing, a portion of the portfolio currently underwritten via QBE’s Lloyd’s Syndicates 386 and 2999 was reinsured to Enstar’s Syndicate 2008.

As a result of this LPT transaction, we assumed net loss reserves of $2.0 billion in exchange for consideration of $1.9 billion1, and recorded a $179 million deferred charge asset (“DCA”).

•In June 2023, one of our wholly-owned subsidiaries completed an agreement with RACQ Insurance Limited (“RACQ”) to reinsure 80% of RACQ’s motor vehicle Compulsory Third Party (“CTP”) insurance liabilities, covering accident years 2021 and prior.

At closing, we assumed net loss reserves of $179 million in exchange for consideration of $179 million1.

•During the second quarter of 2023, we assumed active claims management control on a 2022 LPT transaction with Argo Group International Holdings, Ltd. (“Argo”) pursuant to terms of the agreement.

Completed Unwind of Enhanzed Re’s Reinsurance Transactions

•In November 2022, our subsidiary Enhanzed Reinsurance Ltd. (“Enhanzed Re”) completed a novation of the reinsurance of a closed block of life annuity policies to Monument Re Limited, a subsidiary of Monument Insurance Group Limited (“Monument Re”).

◦Given our one quarter lag in reporting Enhanzed Re’s results, we recognized a $275 million net gain on novation within other income in the first quarter of 2023, which was comprised of2:

▪the reclassification benefit to income of $363 million from accumulated other comprehensive income (“AOCI”) related to the settlement of the novated future policyholder benefit liabilities;

▪the loss of $39 million on the carrying value of the net assets of $133 million as of the closing date of the transaction in exchange for cash consideration of $94 million; and

▪a deferral of a portion of the net gain to be earned over the settlement period of the novated liabilities, equal to $49 million, for our preexisting 20% ownership interest in Monument Re.

◦Our net earnings attributable to Enstar were further reduced by $81 million, representing the amount attributable to Allianz SE’s (“Allianz”) 24.9% noncontrolling interest in Enhanzed Re at the time of the transaction. In total, first quarter 2023 net earnings attributable to Enstar from this novation transaction were $194 million.

•On December 28, 2022, Enhanzed Re repurchased the entire 24.9% ownership interest Allianz held in Enhanzed Re for $175 million, which was based on the final net book value of Enhanzed Re as of December 31, 2022. Following the repurchase, Enhanzed Re became a wholly-owned subsidiary of Enstar.

•The completion of these transactions resulted in the conclusion of the unwind of Enhanzed Re, achieving an inception to date return from Enhanzed Re of 24%.

1 Refer to Note 2 to our condensed consolidated financial statements for further details, including the composition of consideration received.

2 Refer to “Assumed Life” section for further details.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 9

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Item 2 | Management's Discussion and Analysis | Operational Highlights

Capital Activity

•In March 2023, we repurchased 1,597,712 of our non-voting convertible ordinary shares held by Canada Pension Plan Investment Board (“CPP Investments”) for an aggregate $341 million, representing a price per share of $213.13 and a 5% discount to the trailing 10-day volume weighted average price of our voting ordinary shares at the agreed March 2023 measurement date. The shares comprised all of our outstanding Series C and Series E non-voting ordinary shares.

•In May 2023, we amended and restated our existing revolving credit agreement to increase the total commitments under the revolving credit facility from $600 million to $800 million, with the option to request additional commitments up to an aggregate amount of $200 million. Under the amended facility, we may borrow revolving loans or request the issuance of syndicated or fronted letters of credit.

•In June 2023, we received an upgrade from Standard & Poor’s (“S&P”) on our long-term issuer credit rating to BBB+, with a stable outlook.

•In July 2023, we entered into an $800 million amended and restated letter of credit facility agreement, which replaced our existing $800 million letter of credit facility agreement under which the commitment period was due to expire in August 2023.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 10

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Consolidated Results of Operations - For the Three and Nine Months Ended September 30, 2023 and 2022

Primary GAAP Financial Measures

We use the following GAAP measures to manage the company and monitor our performance:

•Net earnings and net earnings attributable to Enstar ordinary shareholders, which collectively provide a measure of our performance focusing on underwriting, investment and expense results;

•Comprehensive income attributable to Enstar, which provides a measure of the total return, including unrealized gains and losses on fixed maturities, AFS investments, as well as other elements of other comprehensive income;

•Book value per share (“BVPS”), which we use to measure the value of our company over time;

•Return on equity (“ROE”), which measures our profitability by dividing our earnings attributable to Enstar ordinary shareholders by Enstar ordinary shareholders’ equity;

•Total investment return (“TIR”), which measures the rate of return we obtain, both realized and unrealized, on our investments; and

•Run-off liability earnings (“RLE”) and RLE %, which measure both the dollar amount of prior period development on our acquired portfolios (RLE) and the percentage of prior period development relative to average net loss reserves, calculated by dividing our prior period net incurred losses and LAE by our average net loss reserves (RLE %).

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 11

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

The following table sets forth certain condensed consolidated financial information:

			Three Months Ended																								Nine Months Ended
			September 30,												$ / pp Change												September 30,												$ / pp Change
			2023						2022															2023						2022
			(in millions of U.S. dollars, except per share data)
Underwriting Results
Net premiums earned			$	14					$	4					$	10											$	29					$	52					$	(23)
Net incurred losses and LAE
Current period			5						13						(8)												18						39						(21)
Prior period			(15)						(141)						126												(35)						(476)						441
Total net incurred losses and LAE			(10)						(128)						118												(17)						(437)						420
Policyholder benefit expenses			—						7						(7)												—						25						(25)
Acquisition costs			—						—						—												6						20						(14)
Investment Results
Net investment income			143						116						27												471						302						169
Net realized losses			(14)						(36)						22												(33)						(111)						78
Net unrealized gains (losses)			20						(546)						566												200						(1,518)						1,718
(Losses) earnings from equity method investments			(3)						(20)						17												22						12						10
Other (expense) income			(2)						(4)						2												280						33						247
Amortization of net deferred charge assets			34						21						13												75						60						15
General and administrative expenses			91						66						25												265						234						31
																											$	—
NET EARNINGS (LOSS)			51						(466)						517												609						(1,180)						1,789
Net (earnings) loss attributable to noncontrolling interests			(4)						43						(47)												(99)						74						(173)
NET EARNINGS (LOSS) ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS			$	38					$	(432)					$	470											$	483					$	(1,133)					$	1,616
COMPREHENSIVE (LOSS) INCOME ATTRIBUTABLE TO ENSTAR			$	(35)					$	(499)					$	464											$	242					$	(1,521)					$	1,763
GAAP measures:
ROE			0.9		%				(9.4)		%				10.3		pp										10.8		%				(19.5)		%				30.3		pp
Annualized ROE																											14.4		%				(26.0)		%				40.4		pp
RLE																											0.3		%				4.0		%				(3.7)		pp
Annualized TIR																											4.7		%				(13.0)		%				17.7		pp
Non-GAAP measures:
Adjusted ROE*			2.5		%				(2.5)		%				5.0		pp										10.8		%				(5.2)		%				16.0		pp
Annualized Adjusted ROE*																											14.4		%				(6.9)		%				21.3		pp
Adjusted RLE *																											0.6		%				1.9		%				(1.3)		pp
Annualized Adjusted TIR*																											5.3		%				(1.0)		%				6.3		pp
																											As of												$ Change
																											September 30, 2023						December 31, 2022
GAAP measure:
BVPS																											$	282.37					$	262.24					$	20.13
Non-GAAP measure:
Adjusted BVPS*																											$	277.01					$	258.92					$	18.09

pp - Percentage point(s)

*Non-GAAP measure; refer to "Non-GAAP Financial Measures" section for reconciliation to the applicable GAAP financial measure.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 12

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Overall Results

Three Months Ended September 30, 2023 versus 2022:

Net earnings attributable to Enstar ordinary shareholders for the three months ended September 30, 2023 were $38 million, in comparison to a net loss of $432 million in the comparative quarter, as a result of:

•Favorable total investment returns recognized in earnings of $146 million for the three months ended September 30, 2023, in comparison to a negative total investment return recognized in earnings of $486 million for the comparative quarter, consisting of the aggregate of net investment income, net realized gains (losses), net unrealized gains (losses) and earnings (losses) from equity method investments. The total investment return was driven by:

◦Net realized and unrealized gains on our other investments, including equities of $86 million, in comparison to net realized and unrealized losses in the comparative quarter of $164 million;

◦An increase in net investment income of $27 million, consistent with the increasing investment income we have earned on a sequential quarterly basis, primarily due to reinvestment of fixed maturities at higher yields, deployment of consideration received from deals closed over the past 12 months and the impact of rising interest rates on our fixed maturities securities that are subject to floating interest rates; and

◦Net realized and unrealized losses on our fixed maturities of $80 million for the three months ended September 30, 2023, compared to net realized and unrealized losses on our fixed maturities of $418 million for the three months ended September 30, 2022. The net result for the three months ended September 30, 2023 was favorable on a comparative basis due to the less significant increase in interest rates relative to the comparative quarter.

This was partially offset by:

•A decrease of $126 million in favorable development in net incurred losses and LAE for prior periods in comparison to the three months ended September 30, 2022. Third quarter 2023 net favorable development of $15 million was primarily due to a reduction in our estimates of net ultimate losses and provisions for ULAE of $31 million, partially offset by a $12 million increase in the fair value of our 2017 and 2018 LPT liabilities where we elected the fair value option due to a modest decrease in third quarter 2023 U.K. corporate bond yields based on the mix of the underlying liabilities within such LPTs (which more than offset the impact of a modest increase in non-U.K. corporate bond yields in the same period for non U.K. LPTs). Third quarter 2022 net favorable development of $141 million was primarily due to a reduction in our estimates of net ultimate losses and provisions for ULAE of $63 million and an $82 million reduction in the fair value of liabilities where we elected the fair value option due to an increase in third quarter 2022 global corporate bond yields resulting in higher discount rates. This resulted in RLE of 0.1% for the three months ended September 30, 2023 in comparison to RLE of 1.2% in the comparative quarter.

The above factors contributed to net earnings of $51 million for the three months ended September 30, 2023 as compared to a net loss of $466 million in the comparative quarter, as well as net earnings attributable to Enstar ordinary shareholders of $38 million as compared to net losses attributable to Enstar ordinary shareholders of $432 million in the comparative quarter.

Consequently, our ROE was positive 0.9% in the current quarter as compared to negative (9.4)% for the three months ended September 30, 2022.

Comprehensive loss attributable to Enstar for the three months ended September 30, 2023 was $35 million as compared to $499 million in the comparative quarter. The third quarter 2023 comprehensive loss was primarily due to unrealized losses on fixed maturities, AFS, net of reclassification adjustments, of $82 million, partially offset by net earnings of $51 million. The unrealized losses on our fixed maturities, AFS, combined with our favorable investment results, described above, contributed to a net favorable Annualized TIR of 1.8% for the three months ended September 30, 2023, in comparison to a negative Annualized TIR of (13.1)% in the comparative quarter.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 13

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Nine Months Ended September 30, 2023 versus 2022:

Net earnings attributable to Enstar ordinary shareholders for the nine months ended September 30, 2023 were $483 million, in comparison to a net loss of $1.1 billion in the comparative period, as a result of:

•Favorable total investment returns recognized in earnings of $660 million for the nine months ended September 30, 2023, in comparison to a negative total investment return recognized in earnings of $1.3 billion for the comparative period, consisting of the aggregate of net investment income, net realized gains (losses), unrealized gains (losses) and earnings (losses) from equity method investments. The total investment return was primarily driven by:

◦Net realized and unrealized gains on our other investments, including equities of $295 million, in comparison to net realized and unrealized losses in the comparative period of $468 million, as a result of strong global equity market performance, particularly in the first quarter of 2023, and tightening high yield credit spreads for the nine months ended September 30, 2023, compared to the challenging market environment for the nine months ended September 30, 2022;

◦An increase in net investment income of $169 million, consistent with the increasing investment income we have earned on a sequential quarterly basis, primarily due to reinvestment of fixed maturities at higher yields, deployment of consideration received from deals closed over the past 12 months and the impact of rising interest rates on our fixed maturities that are subject to floating interest rates; and

◦Net realized and unrealized losses on our fixed maturities of $128 million for the nine months ended September 30, 2023, in comparison to net realized and unrealized losses in the comparative period of $1.2 billion. The net result was favorable on a comparative basis due to the less significant increase in interest rates relative to the comparative period.

•An increase in other income of $247 million, largely driven by the first quarter 2023 net gain recognized from the novation of the Enhanzed Re reinsurance of a closed block of life annuity policies.

This was partially offset by:

•A decrease of $441 million in favorable development in net incurred losses and LAE for prior periods in comparison to the prior year comparative period. Year to date 2023 net favorable development of $35 million was primarily due to a reduction in our estimates of net ultimate losses and provisions for ULAE of $72 million, partially offset by a $24 million increase in the fair value of our 2017 and 2018 LPT liabilities where we elected the fair value option predominantly driven by a second quarter 2023 out-of-period adjustment to correct the portion of the change in fair value related to the Instrument-specific credit risk from net incurred losses and LAE to AOCI, which had previously been recorded as a benefit to net incurred losses in 2022. Year to date 2022 net favorable development of $476 million was primarily due to a reduction in our estimates of net ultimate losses and provisions for ULAE of $259 million and a $228 million reduction in the fair value of liabilities where we elected the fair value option due to an increase in global corporate bond yields during the nine months ended September 30, 2022. This resulted in RLE of 0.3% for the nine months ended September 30, 2023 in comparison to RLE of 4.0% in the comparative period; and

•Net earnings attributable to noncontrolling interests of $99 million, in comparison to a net loss of $74 million in the comparative period, as a result of recording the portion of the gain on novation of the Enhanzed Re reinsurance of a closed block of life annuity policies attributable to Allianz’s equity interest in Enhanzed Re.

The above factors contributed to net earnings of $609 million for the nine months ended September 30, 2023 as compared to a net loss of $1.2 billion in the comparative period, as well as net earnings attributable to Enstar ordinary shareholders of $483 million as compared to net losses attributable to Enstar ordinary shareholders of $1.1 billion in the comparative period.

Consequently, our ROE was positive 10.8% for the nine months ended September 30, 2023 as compared to negative (19.5)% for the nine months ended September 30, 2022.

Comprehensive income attributable to Enstar for the nine months ended September 30, 2023 was $242 million as compared to comprehensive net loss of $1.5 billion in the comparative period. Year to date 2023 comprehensive income was primarily due to net earnings of $609 million, partially offset by the reclassification adjustment of $363 million associated with the novation described above and net unrealized losses on our fixed maturities, AFS, net of reclassification adjustments, of $16 million. The unrealized losses on our fixed maturities, AFS, combined with our favorable investment return, described above, contributed to a net favorable Annualized TIR of 4.7% for the nine

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 14

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

months ended September 30, 2023, in comparison to a negative Annualized TIR of (13.0)% in the comparative period.

BVPS and Adjusted BVPS* increased by 7.7% and 7.0%, respectively, from December 31, 2022 to September 30, 2023, primarily due to comprehensive income attributable to Enstar for the nine months ended September 30, 2023, which contributed 5.4% to both BVPS and Adjusted BVPS*, combined with the repurchase of all our non-voting convertible ordinary shares at a discount to year-end book value.

As described above, the significant increase in interest rates over the past two years has contributed to cumulative net unrealized losses of $1.2 billion on our fixed maturities and funds held - directly managed held as of September 30, 2023. This has adversely impacted BVPS by $79.01 per share and Adjusted BVPS* by $77.52 per share as of September 30, 2023.

BVPS and Adjusted BVPS* as of December 31, 2022 reported in this Quarterly Report on Form 10-Q reflect the impact of our adoption of ASU 2018-12, which had the effect of retrospectively increasing such measures by $16.04 and $15.83, respectively, from the amounts reported in our Annual Report on Form 10-K for the year ended December 31, 2022. The higher opening BVPS and Adjusted BVPS* for the year negatively impacted our growth in BVPS and Adjusted BVPS* for the nine months ended September 30, 2023, which would have otherwise been 14.7% and 14.0%, respectively. Our future policyholder benefit liabilities, which were adjusted for the retrospective application of ASU 2018-12, were settled in the fourth quarter of 2022 following the completion of the novation as described above, but the transaction was recognized in the first quarter of 2023 as we report the results of Enhanzed Re on a one quarter lag. Consequently, the adoption of ASU 2018-12 had no impact on our BVPS or Adjusted BVPS* as of September 30, 2023.

Similarly, at the time the repurchase of our non-voting convertible ordinary shares was negotiated, the price represented a 13.0% discount to year-end book value as reported in our Annual Report on Form 10-K for the year ended December 31, 2022. Following the adoption of ASU 2018-12 on a retrospective basis, the price paid in the repurchase transaction represented a 23.0% discount to year-end book value as reported in our Quarterly Report on Form 10-Q for the three and nine months ended September 30, 2023.

*Non-GAAP measure; refer to "Non-GAAP Financial Measures" section for reconciliation to the applicable GAAP financial measure.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 15

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Overall Measures of Performance

BVPS and Adjusted BVPS*

BVPS and Adjusted BVPS* increased by 7.7% and 7.0%, respectively, from December 31, 2022 to September 30, 2023, primarily as a result of comprehensive income attributable to Enstar of $242 million for the nine months ended September 30, 2023 and the repurchase of our non-voting convertible ordinary shares at a discount to year-end book value. The adoption of ASU 2018-12 impacted our BVPS and Adjusted BVPS* as of December 31, 2022, as described above. The cumulative impact of net unrealized losses on our fixed maturities and funds held - directly managed adversely impacted BVPS by $79.01 per share and Adjusted BVPS* by $77.52 per share as of September 30, 2023.

ROE and Adjusted ROE*

Three and Nine Months Ended September 30, 2023 versus 2022: ROE increased by 10.3 and 30.3 pp for the three and nine months ended September 30, 2023 compared to 2022, respectively, primarily due to:

i.decreased net realized and unrealized losses on our fixed maturities for the three and nine months ended September 30, 2023 compared to net losses for the equivalent periods ended September 30, 2022, respectively. This contributed 7.2 and 17.1 pp to the increase in ROE for the three and nine months ended September 30, 2023, respectively;

ii.net realized and unrealized gains on other investments, including equities, for the three and nine months ended September 30, 2023, respectively, compared to net losses for the equivalent periods ended September 30, 2022, respectively. This contributed 5.5 and 14.7 pp to the increase in ROE for the three and nine months ended September 30, 2023, respectively;

iii.increased other income, comprised primarily of the first quarter 2023 gain recognized on the novation of the Enhanzed Re reinsurance of a closed block of life annuity policies, which contributed 5.7 pp to the increase in ROE for the nine months ended September 30, 2023; and

iv.increased net investment income, which contributed 5.4 pp to the increase in ROE for the nine months ended September 30, 2023.

These favorable factors were partially offset by:

v. decreased favorable prior period development, or RLE, which offset the increase in ROE by 2.7 and 7.4 pp for the three and nine months ended September 30, 2023, respectively; and

vi.     increased earnings attributable to noncontrolling interests, which offset the increase in ROE by 1.0 and 3.5 pp for the three and nine months ended September 30, 2023, respectively.

Adjusted ROE* increased by 5.0 and 16.0 pp for the three and nine months ended September 30, 2023, respectively, which excludes the impact of net realized and unrealized (losses) gains on our fixed maturities.

*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 16

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

We discuss the results of our operations by aggregating certain captions from our condensed consolidated statements of earnings, as we believe it provides a more meaningful view of our results and eliminates repetition that would arise if captions were discussed on an individual basis.

In order to facilitate analysis, we have grouped the discussion into the following captions:

•Underwriting results: includes net premiums earned, net incurred losses and LAE, policyholder benefit expenses and acquisition costs.

•Investment results: includes net investment income, net realized (losses) gains, net unrealized gains (losses) (recorded through the condensed statements of earnings and other comprehensive income) and earnings (losses) from equity method investments.

•General and administrative results: includes general and administrative expenses.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 17

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Underwriting Results

Our strategy is focused on effectively managing (re)insurance portfolios underwritten in previous years that we assume through our provision of capital release solutions and acquisition of portfolios and businesses in run-off.

Although we have largely exited our active underwriting platforms, we still record net premiums earned and the associated current period net incurred losses and LAE and acquisition costs as a result of the run-off of unearned premiums from transactions completed in recent years.

Premiums earned in the Run-off segment are generally offset by the related current period net incurred losses and LAE and acquisition costs.

The components of underwriting results are as follows:

			Three Months Ended September 30,
			2023																														2022
			Run-off						Assumed Life						Legacy Underwriting						Corporate and other						Total						Run-off						Assumed Life						Legacy Underwriting						Corporate and other						Total
			(in millions of U.S. dollars)
Net premiums earned			$	14					$	—					$	—					$	—					$	14					$	1					$	2					$	1					$	—					$	4
Net incurred losses and LAE:
Current period			5						—						—						—						5						10						—						3						—						13
Prior periods			(31)						—						—						16						(15)						(61)						—						(2)						(78)						(141)
Total net incurred losses and LAE			(26)						—						—						16						(10)						(51)						—						1						(78)						(128)
Policyholder benefit expenses			—						—						—						—						—						—						7						—						—						7
Acquisition costs			—						—						—						—						—						1						—						(1)						—						—
Underwriting results			$	40					$	—					$	—					$	(16)					$	24					$	51					$	(5)					$	1					$	78					$	125

			Nine Months Ended September 30,
			2023																														2022
			Run-off						Assumed Life						Legacy Underwriting						Corporate and other						Total						Run-off						Assumed Life						Legacy Underwriting						Corporate and other						Total
			(in millions of U.S. dollars)
Net premiums earned			$	29					$	—					$	—					$	—					$	29					$	27					$	17					$	8					$	—					$	52
Net incurred losses and LAE:
Current period			18						—						—						—						18						35						—						4						—						39
Prior periods			(72)						—						—						37						(35)						(232)						(29)						2						(217)						(476)
Total net incurred losses and LAE			(54)						—						—						37						(17)						(197)						(29)						6						(217)						(437)
Policyholder benefit expenses			—						—						—						—						—						—						25						—						—						25
Acquisition costs			6						—						—						—						6						18						—						2						—						20
Underwriting results			$	77					$	—					$	—					$	(37)					$	40					$	206					$	21					$	—					$	217					$	444

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 18

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Prior Periods - RLE - Three and Nine Months Ended September 30, 2023 and 2022

The following tables summarize RLE % and Adjusted RLE %* by acquisition year, which management believes is useful in measuring and monitoring performance of our claims management activity on the portfolios that we have acquired. This permits comparability between acquisition years of different loss reserve volumes.

Three Months Ended September 30, 2023:

																					Three Months Ended September 30, 2023
																					RLE																								Adjusted RLE*
Acquisition Year																					RLE / PPD						Average net loss reserves						RLE %						Annualized RLE %						Adjusted RLE / PPD*						Average adjusted net loss reserves*						Adjusted RLE %*						Annualized Adj RLE %*
																					(in millions of U.S. dollars)
2013 and prior																					$	2					$	1,052																	$	2					$	1,112
2014																					13						397																		(10)						69
2015																					2						261																		2						266
2016																					14						638																		15						702
2017																					(34)						536																		(27)						780
2018																					2						645																		9						727
2019																					(5)						986																		(3)						1,496
2020																					1						425																		1						425
2021																					8						3,248																		31						3,589
2022																					12						2,598												1.9		%				12						2,598
2023																					—						1,761																		—						1,761
Total																					$	15					$	12,547					0.1		%				0.5		%				$	32					$	13,525					0.2		%				0.9		%

*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.

Our RLE % was 0.1%, or nearly flat, for the three months ended September 30, 2023, as favorable reductions in estimates of net ultimate losses and reductions in provisions for ULAE were partially offset by net unfavorable changes in the fair value of liabilities for which we have elected the fair value option and amortization of fair value adjustments.

Favorable RLE in the 2014 acquisition year was driven by favorable movement on our professional indemnity/directors and officers, all other, and marine, aviation and transit lines of business due to favorable claims experience, partially offset by adverse development on our general casualty and property lines of business due to adverse claims experience.

Favorable RLE in the 2016 acquisition year was driven by favorable claims development on our professional indemnity/directors and officers line of business.

Adverse RLE in the 2017 acquisition year was driven by $27 million of adverse development on our all other line of business, as a result of identified deterioration on abuse claims, in addition to a $7 million increase in the fair value of liabilities for which we have elected the fair value option as a result of decreases in U.K. corporate bond yields. The corporate bond yields, which form a component of the discount rate used to calculate the fair value of the liabilities, are matched to the original currencies of the underlying loss portfolios, of which GBP is the predominant currency for those portfolios that we have elected to measure at fair value using the fair value option.

Favorable RLE in the 2021 acquisition year was driven by continued favorable claims experience on our workers’ compensation line of business.

Favorable RLE in the 2022 acquisition year was driven by favorable development on our property line of business as a result of favorable claims experience.

Our Adjusted RLE %* was positively impacted by the net reduction in estimates of net ultimate losses and reductions in provisions for ULAE relating to the Run-off segment. It also excludes the unfavorable impact of the changes in the discount rate upon the fair value of liabilities where we have elected the fair value option and the amortization of fair value adjustments relating to purchased subsidiaries.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 19

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Three Months Ended September 30, 2022:

																					Three Months Ended September 30, 2022
																					RLE																								Adjusted RLE*
Acquisition Year																					RLE / PPD						Average net loss reserves						RLE %						Annualized RLE %						Adjusted RLE / PPD*						Average adjusted net loss reserves*						Adjusted RLE %*						Annualized Adj RLE %*
																					(in millions of U.S. dollars)
2013 and prior																					$	8					$	733																	$	7					$	658
2014																					17						711																		4						87
2015																					7						308																		7						314
2016																					3						706																		3						778
2017																					71						592																		4						805
2018																					5						840																		(9)						932
2019																					10						1,139																		12						1,672
2020																					(13)						600																		(13)						600
2021																					29						3,892																		42						4,338
2022																					4						2,651																		4						2,651
Total																					$	141					$	12,172					1.2		%				4.6		%				$	61					$	12,835					0.5		%				1.9		%

*Non-GAAP measure; refer to “Non-GAAP Financial Measures” section for reconciliation to the applicable GAAP financial measure.

Overall, our RLE % was positively impacted by a reduction of $82 million in the fair value of liabilities for which we have elected the fair value option in the 2017 and 2018 acquisition years as a result of increases in global corporate bond yields.

Favorable development as a result of lower claim activity on our marine, aviation, and transit line of business and favorable claim settlements on our workers’ compensation line of business had a favorable impact on RLE in acquisition year 2019.

Acquisition year 2018 benefited from the favorable development on our marine, aviation and transit and workers’ compensation lines of business similar to our experience with the 2019 acquisition year, with a partially offsetting increase in estimates of net ultimate losses as a result of worse than expected claims experience and adverse development on claims in relation to our general casualty and motor lines of business. This adverse experience also impacted acquisition year 2020.

Acquisition year 2021 benefited from favorable claim settlements on our workers’ compensation line of business, with a partially offsetting adverse impact from worse than expected claims experience on our general casualty line of business.

Our Annualized Adjusted RLE %* was positively impacted by the net reduction in estimates of net ultimate losses, as described above, but excludes the favorable impact of the changes in the discount rate on the fair value of liabilities where we have elected the fair value option.

Enstar Group Limited | Third Quarter 2023 | Form 10-Q                 20

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Item 2 | Management's Discussion and Analysis | Consolidated Results of Operations

Nine Months Ended September 30, 2023:

																					Nine Months Ended September 30, 2023
																					RLE																								Adjusted RLE*
Acquisition Year																					RLE / PPD						Average net loss reserves						RLE %						Annualized RLE %						Adjusted RLE / PPD*						Average adjusted net loss reserves*						Adjusted RLE %*						Annualized Adj RLE %*
																					(in millions of U.S. dollars)
2013 and prior																					$	5					$	847																	$	8					$	839
2014																					15						524																		(13)						62
2015																					5						273																		6						291
2016																					15						654																		18						721
2017																					(35)						553																		(25)						787
2018																					(8)						696																		12						781
2019																					(4)						1,018																		(2)						1,535
2020<