Form 8-K - Current report

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d)

of the Securities Exchange Act of 1934

Date of report (Date of earliest event reported): February 20, 2024

Enstar Group Limited

(Exact name of registrant as specified in its charter)

Bermuda

001-33289

N/A

(State or other jurisdiction

of incorporation)

(Commission

File Number)

(IRS Employer

Identification No.)

A.S. Cooper Building, 4th Floor, 26 Reid Street

Hamilton, Bermuda HM 11

(Address of principal executive offices) (Zip Code)

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

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2. below):


☐			Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐			Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐			Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐			Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

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% Fixed-to-Floating Rate	ESGRP	The NASDAQ Stock Market	LLC
Perpetual Non-Cumulative Preferred Share, Series D, Par Value $1.00 Per Share
Depositary Shares, Each Representing a 1/1,000th Interest	ESGRO	The NASDAQ Stock Market	LLC
in a 7.00% Perpetual Non-Cumulative Preferred Share, Series E, Par Value $1.00 Per Share

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

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. ☐

Item 2.02. Results of Operations and Financial Condition.

On February 20, 2024, Enstar Group Limited (the "Company") issued a press release announcing its results for the year ended December 31, 2023 (the "Press Release"), a copy of which is furnished with this report as Exhibit 99.1 and incorporated herein by reference, and a Financial Supplement for the year ended December 31, 2023 (the "Financial Supplement"), a copy of which is furnished with this report as Exhibit 99.2 and incorporated herein by reference. In addition, the Company posted an investor presentation (the "Investor Presentation") on its website that the Company will be presenting and discussing at the 2024 Bank of America Financial Services Conference, a copy of which is furnished with this report as Exhibit 99.3 and incorporated herein by reference. The Press Release, the Financial Supplement and the Investor Presentation are available on the "Investor Relations" page of the Company's website located at www.enstargroup.com.

The information contained in the Press Release, the Financial Supplement and the Investor Presentation is summary information that is intended to be considered in the context of the Company's Securities and Exchange Commission ("SEC") filings and other public announcements that the Company may make, by press release or otherwise, from time to time. The Company undertakes no duty or obligation to publicly update or revise the information contained in the Press Release, the Financial Supplement and the Investor Presentation, although it may do so from time to time as its management believes is warranted. Any such updating may be made through the filing of other reports or documents with the SEC, through press releases or through other public disclosure.

The information presented in Item 2.02 of this Current Report on Form 8-K and Exhibits 99.1, 99.2 and 99.3 shall not be deemed to be "filed" for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, unless the Company specifically states that the information is to be considered “filed” under the Exchange Act or specifically incorporates it by reference into a filing under the Securities Act of 1933, as amended.

Item 9.01. Financial Statements and Exhibits.

Exhibits


Exhibit No.						Description

99.1						Press Release, dated February 20, 2024.

99.2						Financial Supplement for the year ended December 31, 2023.

99.3						2024 Bank of America Financial Services Conference Presentation.

101						Pursuant to Rule 406 of Regulation S-T, the cover page information in formatted in Inline XBRL

104						Cover page Interactive Data File (embedded within the Inline XBRL document and included in Exhibit 101)

SIGNATURES

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


	ENSTAR GROUP LIMITED

February 20, 2024	By:	/s/ Matthew Kirk
		Matthew Kirk
		Chief Financial Officer

Press Release

Date: February 20, 2024 Contact: Enstar Communications

For Release: Immediately Telephone: +1 (441) 292-3645

Enstar Group Limited Reports Fourth Quarter and 2023 Year-End Results

•Full year 2023 Net Income attributable to Enstar Ordinary Shareholders of $1.1 billion, Return on Equity of 24.2% and Growth in Book Value per Ordinary Share of 31.0% to $343.45 (Fully Diluted* $336.72)

•Fourth Quarter Net Income attributable to Enstar Ordinary Shareholders of $599 million and Return on Equity of 13.7%

•Closed Previously Announced Transaction with AIG

•Repurchased 841,735 Voting Ordinary Shares for $191 Million at a Significant Discount to Book Value Per Ordinary Share

HAMILTON, Bermuda - February 20, 2024 - Enstar Group Limited (Nasdaq: ESGR) today announced financial results for the fourth quarter and full year 2023.

Fourth Quarter 2023 Highlights:

•Net income attributable to Enstar ordinary shareholders of $599 million, or $39.71 per diluted ordinary share, for the quarter compared to net loss attributable to Enstar ordinary shareholders of $227 million, or $13.26 per diluted ordinary share, for the three months ended December 31, 2022.

•Return on equity ("ROE") of 13.7% and Adjusted ROE* of 9.0% for the quarter compared to 5.5% and 4.0%, respectively, in the fourth quarter of 2022. ROE performance was driven by investment returns of $463 million and a tax benefit from the enactment of the Bermuda Corporate Income Tax Act 2023 in December 2023 of $205 million. Adjusted ROE* excludes $194 million of net realized and unrealized gains on our fixed maturities and funds held - directly managed.

•Run-off liability earnings ("RLE") of $96 million for the quarter was driven by favorable development on our workers' compensation and property lines of business and a reduction in the provisions for ULAE, partially offset by a charge to increase the value of certain portfolios that are held at fair value due to decreases in global corporate bond yields and adverse development on our general casualty line of business. In comparison, RLE of $280 million in the comparative quarter was positively impacted by income resulting from reductions in the value of certain portfolio liabilities that are held at fair value due to increases in global corporate bond yields, favorable development in our workers’ compensation and marine, aviation and transit lines of business, and the recognition of a gain on commutation of Enhanzed Re’s catastrophe reinsurance business. The comparative annual results were partially offset by adverse development on our general casualty and motor lines of business.

•Annualized total investment return (“TIR”) of 14.8% and Annualized Adjusted TIR* of 5.5% compared to 3.5% and 1.9%, respectively, for the three months ended December 31, 2022. Recognized investment results benefited from net realized and unrealized gains on our fixed maturities, including other comprehensive income (“OCI”) of $414 million, net investment income of $176 million and net unrealized gains on our other investments, including equities, of $102 million.

Enstar Group Limited | 2023 Press Release 1

•Signed agreement with American International Group, Inc. (“AIG”) to provide protection to AIG on its retained exposure to adverse development on Validus Re carried loss reserves, up to a limit of $400 million. The agreement became effective as of November 1, 2023, corresponding to the closing of AIG’s sale of Validus Re to RenaissanceRe.

•Repurchased 841,735 voting ordinary shares for $191 million at a price per share of $227.18, representing a 5% discount to the trailing 10-day volume weighted average price of our voting ordinary shares at the agreed November 2023 measurement date.

•Acquired remaining 41.0% equity interest in StarStone Specialty Holdings Limited (“SSHL”) in exchange for total consideration of $182 million. Following the completion of the transaction, SSHL became a wholly-owned subsidiary and we no longer have any ownership interest in Atrium.

* Non-GAAP measure; refer to "Non-GAAP Financial Measures" further below for explanatory notes and a reconciliation to the most directly comparable GAAP measure.

Dominic Silvester, Enstar CEO, said:

“We finished 2023 strong off the back of an excellent fourth quarter, as we received sizeable contributions from our investment portfolio and generated solid run-off liability earnings, which resulted in ROE for the full year of 24.2%. In addition, we repurchased $532 million of shares during the year, which contributed to our total growth in book value.”

“Turning to M&A, we maintained our leading market position through our completed loss portfolio transfer transactions with QBE and RACQ, as well as our bespoke agreement with AIG - all in acquiring $2.2 billion of liabilities. Looking ahead, we continue to see demand for our innovative legacy solutions and are confident that our strategy and robust business model will ensure we continue to meet our clients’ evolving needs as the dominant legacy player, while driving long-term shareholder value.”

Year Ended December 31, 2023 Highlights:

•Net income attributable to Enstar ordinary shareholders of $1.1 billion, or $68.47 per diluted ordinary share, compared to net loss attributable to Enstar ordinary shareholders of $906 million, or $52.65 per diluted ordinary share, for the year ended December 31, 2022.

•ROE of 24.2% and Adjusted ROE* of 18.8%, compared to (15.6)% and (1.1)%, respectively, for the year ended December 31, 2022. ROE performance was driven by investment returns of $1.1 billion, a tax benefit from the enactment of the Bermuda Corporate Income Tax Act 2023 of $205 million and a year-to-date net gain recognized on the completion of the novation of the Enhanzed Re reinsurance of a closed block of life annuity policies of $196 million.

•RLE of $131 million was driven by favorable development on our workers' compensation and property lines of business and a reduction in the provisions for ULAE, partially offset by charges to increase the value of certain portfolios that are held at fair value and adverse development on our general casualty line of business. In comparison, RLE of $756 million for the year ended December 31, 2022 was positively impacted by favorable development in our workers’ compensation and marine, aviation and transit lines of business and a reduction in the provisions for ULAE, as well as from reductions in the value of certain portfolio liabilities that are held at fair value. The favorable results in 2022 were partially offset by adverse development in our general casualty and motor lines of business.

•TIR of 7.2% and Adjusted TIR* of 5.3%, compared to (9.0)% and (0.2)%, respectively, for the year ended December 31, 2022. Recognized investment results benefited from net unrealized gains on our other investments, including equities, of $397 million, net investment income of $647 million, and net realized and unrealized gains on our fixed maturities, including OCI of $288 million.

•Completed LPT agreements with certain subsidiaries of QBE Insurance Group Limited (“QBE”) and with RACQ Insurance Limited (“RACQ”). At closing, we assumed net loss reserves of $2.0 billion from QBE and $179 million from RACQ in exchange for consideration of $1.9 billion and $179 million, respectively.

•Amended and restated our existing revolving credit agreement, increasing commitments from $600 million to $800 million and increasing the term by five years.

Enstar Group Limited | 2023 Press Release 2

•In addition to the voting ordinary shares repurchased in the fourth quarter, repurchased our remaining 1,597,712 non-voting convertible ordinary shares outstanding for $341 million at a price per share of $213.13, representing a 5% discount to the trailing 10-day volume weighted average price of our voting ordinary shares at the agreed March 2023 measurement date.

* Non-GAAP measure; refer to "Non-GAAP Financial Measures" further below for explanatory notes and a reconciliation to the most directly comparable GAAP measure.

Enstar Group Limited | 2023 Press Release 3

Key Financial and Operating Metrics

We use the following GAAP and Non-GAAP measures to monitor the performance of and manage the company:


	Year Ended				Year Ended
	December 31,				December 31,
		2023			2022			$ / pp / bp Change			2021			$ / pp / bp Change
		(in millions of U.S. dollars, except per share data)
Key Earnings Metrics
Net income (loss) attributable to Enstar ordinary shareholders		$	1,082		$	(906)		$	1,988		$	502		$	(1,408)
Adjusted operating income (loss) attributable to Enstar ordinary shareholders*		$	1,102		$	(61)		$	1,163		$	565		$	(626)
ROE		24.2		%	(15.6)		%	39.8		pp	7.9		%	(23.5)		pp

Adjusted ROE*		18.8		%	(1.1)		%	19.9		pp	10.1		%	(11.2)		pp


Key Run-off Metrics
Prior period development		$	131		$	756		$	(625)		$	403		$	353
Adjusted prior period development*		$	227		$	489		$	(262)		$	381		$	108
RLE		1.1		%	6.3		%	(5.2)		pp	3.9		%	2.4		pp
Adjusted RLE*		1.8		%	3.9		%	(2.1)		pp	3.6		%	0.3		pp

Key Investment Return Metrics





Total investable assets		$	18,243		$	19,540		$	(1,297)		$	21,708		$	(2,168)
Adjusted total investable assets*		$	18,968		$	21,367		$	(2,399)		$	21,619		$	(252)
Investment book yield		3.86		%	2.47		%	139		bp	1.84		%	63		bp
TIR		7.2		%	(9.0)		%	16.2		pp	2.0		%	(11.0)		pp
Adjusted TIR*		5.3		%	(0.2)		%	5.5		pp	3.6		%	(3.8)		pp


		As of						As of
Key Shareholder Metrics		December 31, 2023			December 31, 2022						December 31, 2021
Book value per ordinary share		$	343.45		$	262.24		$	81.21		$	329.20		$	(66.96)
Fully diluted book value per ordinary share*		$	336.72		$	258.92		$	77.80		$	323.43		$	(64.51)

pp - Percentage point(s)

bp - Basis point(s)

*Non-GAAP measure; refer to "Non-GAAP Financial Measures" further below for explanatory notes and a reconciliation to the most directly comparable GAAP measure.

Enstar Group Limited | 2023 Press Release 4

Results of Operations By Segment - For the Years Ended December 31, 2023, 2022 and 2021

Run-off Segment

The following is a discussion and analysis of the results of operations for our Run-off segment.


	2023		2022		$ Change		2021		$ Change
REVENUES	(in millions of U.S. dollars)
Net premiums earned	$	43	$	40	$	3	$	182	$	(142)


Other income:
Reduction in estimates of net ultimate defendant A&E liabilities - prior periods	(1)		2		(3)		38		(36)
Reduction in estimated future defendant A&E expenses	2		1		1		5		(4)
All other income	9		19		(10)		30		(11)
Total other income	10		22		(12)		73		(51)
Total revenues	53		62		(9)		255		(193)

EXPENSES
Net incurred losses and LAE:
Current period	30		44		(14)		144		(100)
Prior period	(226)		(486)		260		(338)		(148)
Total net incurred losses and LAE	(196)		(442)		246		(194)		(248)
Acquisition costs	10		22		(12)		44		(22)
General and administrative expenses	177		143		34		188		(45)
Total expenses	(9)		(277)		268		38		(315)
SEGMENT NET INCOME	$	62	$	339	$	(277)	$	217	$	122

Overall Results

2023 versus 2022: Net income from our Run-off segment decreased by $277 million, primarily due to:

•A $260 million decrease in favorable prior period development (“PPD”), mainly driven by a $198 million decrease in the reduction in estimates of net ultimate losses in comparison to 2022.

◦Results for the year ended December 31, 2023 were driven by favorable development of $200 million on our workers’ compensation line of business as a result of continued favorable claim settlements, most notably in the 2018, 2019 and 2021 acquisition years. We also had favorable development of $68 million on our property line of business relating to the 2022 acquisition year as a result of continued favorable claims experience; partially offset by

◦Adverse development on our general casualty line of business of $127 million, most notably impacting the 2019 and 2020 acquisition years, driven by increased average incurred losses in comparison to IBNR reserve assumptions.

◦Results for the year ended December 31, 2022 were driven by favorable development of $318 million on our workers’ compensation line of business as a result of favorable claim settlements, most notably in the 2017 to 2021 acquisition years. We also had favorable development of $56 million on our marine, aviation and transit lines of business relating to the 2014, 2018 and 2019 acquisition years as a result of favorable experience across a variety of claim types; partially offset by

◦Adverse development on our general casualty and motor lines of business of $57 million and $74 million, respectively, most notably impacting the 2020 acquisition year, as a result of worse than expected claims experience, adverse development on claims and higher than expected claims severity.

•An increase in general and administrative expenses of $34 million, primarily driven by an increase in salaries and benefits expenses and professional fees; and

•Reductions in current period net incurred losses and LAE and acquisition costs that were greater than our reductions in net premiums earned, following our exit of our StarStone International business beginning in 2020.

Enstar Group Limited | 2023 Press Release 5

2022 versus 2021: Net income from our Run-off segment increased by $122 million, primarily due to:

•A $148 million increase in favorable PPD, mainly driven by a $78 million increase in the reduction in estimates of net ultimate losses in comparison to 2021.

•As described above, results for the year ended December 31, 2022 were driven by favorable development on our workers’ compensation and marine, aviation and transit lines of business, partially offset by adverse development on our general casualty and motor lines of business.

•Results for the year ended December 31, 2021 were primarily related to favorable development on our workers’ compensation, property and marine, aviation and transit lines of business as a result of better than expected claims experience and favorable results from actuarial reviews, partially offset by adverse development on our general casualty line of business due to an increase in opioid exposure and increased expectations of latent claims and a lengthening of the payment pattern related to our 2019 acquisition year.

•A decrease in general and administrative expenses of $45 million, primarily driven by a continued decrease in salaries and benefits and other costs following our exit of our StarStone business beginning in 2020 and a reduction in IT costs as a result of reduced project activity; partially offset by

•A reduction in other income of $51 million, primarily driven by lower favorable prior period development related to our defendant A&E liabilities; and

•Reductions in current period net incurred losses and LAE and acquisition costs that were less than our reductions in net premiums earned, following our exit of our StarStone International business beginning in 2020.

Enstar Group Limited | 2023 Press Release 6

Investments Segment

The following is a discussion and analysis of the results of operations for our Investments segment.


	2023		2022		$ Change		2021		$ Change
REVENUES	(in millions of U.S. dollars)
Net investment income:
Fixed income securities	$	539	$	380	$	159	$	273	$	107
Cash and restricted cash	36		8		28		—		8
Other investments, including equities	92		82		10		73		9
Less: Investment expenses	(20)		(25)		5		(37)		12
Total net investment income	647		445		202		309		136
Net realized (losses) gains:
Fixed income securities	(65)		(111)		46		(4)		(107)
Other investments, including equities	—		—		—		(57)		57
Total net realized (losses) gains	(65)		(111)		46		(61)		(50)
Net unrealized gains (losses):
Fixed income securities, trading	131		(1,060)		1,191		(203)		(857)
Other investments, including equities	397		(433)		830		384		(817)
Total net unrealized gains (losses)	528		(1,493)		2,021		181		(1,674)
Total revenues	1,110		(1,159)		2,269		429		(1,588)

EXPENSES
General and administrative expenses	43		37		6		37		—
Total expenses	43		37		6		37		—

Income (losses) from equity method investments	13		(74)		87		93		(167)
SEGMENT NET INCOME (LOSS)	$	1,080	$	(1,270)	$	2,350	$	485	$	(1,755)

Overall Results

2023 versus 2022: Net income from our Investments segment was $1.1 billion compared to a net loss of $1.3 billion in 2022. The favorable movement of $2.4 billion was primarily due to:

•Net realized and unrealized gains on our fixed income securities of $66 million, driven by a decline in interest rates and tightening of investment grade credit spreads, compared to net realized and unrealized losses of $1.2 billion in 2022, primarily due to a significant increase in interest rates and widening of investment grade credit spreads;

•Net unrealized gains on our other investments, including equities, of $397 million, in comparison to losses of $433 million in 2022. The favorable variance of $830 million was primarily driven by:

◦Net gains for the year ended December 31, 2023, primarily driven by our public equities, private equity funds, private credit funds, CLO equities, fixed income funds, hedge funds and infrastructure funds, largely as a result of strong global equity market performance and tightening of high yield and leveraged loan credit spreads; in comparison to

◦Net losses for the year ended December 31, 2022, primarily driven by our public equities, fixed income funds, hedge funds and CLO equities, largely as a result of global equity market declines and widening of high yield and loan credit spreads;

•Income from equity method investments of $13 million, in comparison to losses of $74 million in 2022. This was primarily due to income on our investments in Core Specialty and Citco, which included a gain recorded in the fourth quarter of 2023 following our decision to divest our equity interest in Citco, partially offset by losses on our investment in Monument Re during the year ended December 31, 2023, compared to losses on our investments in Monument Re and Core Specialty in 2022; and

•An increase in our net investment income of $202 million, which is primarily due to the reinvestment of fixed maturities at higher yields, deployment of consideration received from LPT and insurance contract transactions

Enstar Group Limited | 2023 Press Release 7

closed over the past 12 months and the impact of rising interest rates on the $3.1 billion of our average fixed maturities outstanding during 2023 that are subject to floating interest rates. Our floating rate investments generated increased net investment income of $89 million, which equates to an increase of 246 basis points on those investments in comparison to 2022.

2022 versus 2021: Net loss from our Investments segment was $1.3 billion compared to net income of $485 million in 2021. The unfavorable movement of $1.8 billion was primarily due to:

•An increase in net realized and unrealized losses on our fixed income securities of $964 million, driven by rising interest rates and widening of investment grade credit spreads in 2022;

•Net unrealized losses on our other investments, including equities, of $433 million in 2022, in comparison to net realized and unrealized gains of $327 million in 2021. The unfavorable variance of $760 million was primarily driven by negative performance from our public equities, fixed income funds, CLO equities and hedge funds in 2022 as a result of significant volatility in global equity markets and widening of high yield and leveraged loan credit spreads; and

•Losses from equity method investments of $74 million, in comparison to income of $93 million in 2021, primarily due to losses on our investments in Monument Re and Core Specialty in 2022 and our acquisition of the controlling interest in Enhanzed Re, effective September 1, 2021. Prior to that date, the results of Enhanzed Re were recorded in income from equity method investments. Our consolidated net loss from Enhanzed Re for the year ended December 31, 2022 was $235 million which compared to $82 million from Enhanzed Re that was included in equity method investment income in 2021; partially offset by

•An increase in our net investment income of $136 million, which is primarily due to the investment of new premium and reinvestment of fixed maturities at higher yields and the impact of rising interest rates on the $2.9 billion of our average fixed maturities outstanding during the period that are subject to floating interest rates. Our floating rate investments generated increased net investment income of $59 million, which equates to an increase of 195 basis points on those investments in comparison to 2021.

Total investment losses on the fixed maturities that supported our Enhanzed Re life reinsurance (prior to the novation) for the years ended December 31, 2022 and 2021 were $304 million and $17 million, respectively.

Enstar Group Limited | 2023 Press Release 8

Income and (Loss) by Segment - For the Years Ended December 31, 2023, 2022 and 2021


	Year Ended					Year Ended
	December 31,					December 31,
		2023		2022		$ Change				2021		$ Change
		(in millions of U.S. dollars)
REVENUES
Run-off		$	53	$	62	$	(9)			$	255	$	(193)
Assumed Life		277		17		260				5		12
Investments		1,110		(1,159)		2,269				429		(1,588)
Legacy Underwriting		—		10		(10)				43		(33)
Subtotal		1,440		(1,070)		2,510		—		732		(1,802)
Corporate and other		(11)		12		(23)				57		(45)
Total revenues		$	1,429	$	(1,058)	$	2,487	$	—	$	789	$	(1,847)




SEGMENT NET INCOME (LOSS)
Run-off		$	62	$	339	$	(277)			$	217	$	122
Assumed Life		277		40		237				6		34
Investments		1,080		(1,270)		2,350				485		(1,755)
Legacy Underwriting		—		—		—				—		—
Total segment net income (loss)		1,419		(891)		2,310				708		(1,599)












Corporate and other		(337)		(15)		(322)				(206)		191
NET INCOME (LOSS) ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS		$	1,082	$	(906)	$	1,988			$	502	$	(1,408)

Enstar Group Limited | 2023 Press Release 9

Cautionary Statement

This press release 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 can identify these statements by the fact that they do not relate strictly to historical or current facts. They use words such as ‘aim’, ‘anticipate’, ‘estimate’, ‘expect’, ‘intend’, ‘will’, ‘project’, ‘plan’, ‘believe’, ‘target’ and other words and terms of similar meaning in connection with any discussion of future events or performance. 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, 2023 (which will be filed with the Securities and Exchange Commission) and in our Form 10-K for the year ended December 31, 2022 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.

About Enstar

Enstar is a NASDAQ-listed leading global (re)insurance group that offers capital release solutions through its network of group companies in Bermuda, the United States, the United Kingdom, Continental Europe and Australia. A market leader in completing legacy acquisitions, Enstar has acquired over 115 companies and portfolios since its formation. For further information about Enstar, see www.enstargroup.com.

Contacts

For Investors: Matthew Kirk (investor.relations@enstargroup.com)

For Media: Jenna Kerr (communications@enstargroup.com)

Enstar Group Limited | 2023 Press Release 10

ENSTAR GROUP LIMITED

CONSOLIDATED STATEMENTS OF OPERATIONS

For the Three Months Ended December 31, 2023 and 2022 and the Years Ended December 31, 2023, 2022 and 2021


	Three Months Ended December 31,				Year Ended December 31,
	2023		2022		2023		2022		2021
	(expressed in millions of U.S. dollars, except share and per share data)
REVENUES
Net premiums earned	$	14	$	14	$	43	$	66	$	245

Net investment income	176		153		647		455		312
Net realized losses	(10)		(23)		(65)		(111)		(61)
Net unrealized gains (losses)	306		38		528		(1,503)		178
Other (expense) income	(4)		2		276		35		42
Net gain on purchase and sales of subsidiaries	—		—		—		—		73
Total revenues	482		184		1,429		(1,058)		789

EXPENSES
Net incurred losses and loss adjustment expenses
Current period	12		9		30		48		172
Prior periods	(96)		(280)		(131)		(756)		(403)
Total net incurred losses and loss adjustment expenses	(84)		(271)		(101)		(708)		(231)
Policyholder benefit expenses	—		—		—		25		(3)
Amortization of net deferred charge assets	31		20		106		80		55
Acquisition costs	4		3		10		23		57
General and administrative expenses	104		97		369		331		367
Interest expense	23		18		90		89		69
Net foreign exchange losses (gains)	24		12		—		(15)		(12)
Total expenses	102		(121)		474		(175)		302

INCOME (LOSS) BEFORE INCOME TAXES	380		305		955		(883)		487
Income tax benefit (expense)	238		16		250		12		(27)
(Losses) income from equity method investments	(9)		(86)		13		(74)		93


NET INCOME (LOSS)	609		235		1,218		(945)		553
Net (income) loss attributable to noncontrolling interest	(1)		1		(100)		75		(15)
NET INCOME (LOSS) ATTRIBUTABLE TO ENSTAR GROUP LIMITED	608		236		1,118		(870)		538
Dividends on preferred shares	(9)		(9)		(36)		(36)		(36)
NET INCOME (LOSS) ATTRIBUTABLE TO ENSTAR GROUP LIMITED ORDINARY SHAREHOLDERS	$	599	$	227	$	1,082	$	(906)	$	502

Earnings (loss) per ordinary share attributable to Enstar:



Basic	$	40.14	$	13.34	$	69.22	$	(52.65)	$	25.33



Diluted	$	39.71	$	13.26	$	68.47	$	(52.65)	$	24.94
Weighted average ordinary shares outstanding:
Basic	14,923,541		17,021,348		15,631,770		17,207,229		19,821,259
Diluted	15,083,306		17,121,606		15,802,618		17,323,130		20,127,131

Enstar Group Limited | 2023 Press Release 11

ENSTAR GROUP LIMITED

CONSOLIDATED BALANCE SHEETS

As of December 31, 2023 and 2022


	December 31, 2023		December 31, 2022
	(in millions of U.S. dollars, except share data)
ASSETS
Short-term investments, trading, at fair value	$	2	$	14
Short-term investments, available-for-sale, at fair value (amortized cost: 2023 — $62; 2022 — $37)	62		38
Fixed maturities, trading, at fair value	1,949		2,370

Fixed maturities, available-for-sale, at fair value (amortized cost: 2023 — $5,642; 2022 — $5,871; net of allowance: 2023 — $16; 2022 — $33)	5,261		5,223
Funds held	5,251		5,622
Equities, at fair value (cost: 2023 — $615; 2022 — $1,357)	701		1,250
Other investments, at fair value (includes consolidated variable interest entity: 2023 - $59; 2022 - $3)	3,853		3,296

Equity method investments	334		397
Total investments	17,413		18,210
Cash and cash equivalents (includes consolidated variable interest entity: 2023 — $8; 2022 — $0)	564		822
Restricted cash and cash equivalents	266		508



Accrued interest receivable	71		72
Reinsurance balances recoverable on paid and unpaid losses (net of allowance: 2023 — $131; 2022 — $131)	740		856
Reinsurance balances recoverable on paid and unpaid losses, at fair value	217		275
Insurance balances recoverable (net of allowance: 2023 and 2022 — $5)	172		177








Net deferred charge assets	731		658
Other assets	739		576

TOTAL ASSETS	$	20,913	$	22,154
LIABILITIES
Losses and loss adjustment expenses	$	11,196	$	11,721
Losses and loss adjustment expenses, at fair value	1,163		1,286
Future policyholder benefits	—		821
Defendant asbestos and environmental liabilities	567		607

Insurance and reinsurance balances payable	43		100

Debt obligations	1,831		1,829

Other liabilities (includes consolidated variable interest entity: 2023 — $1; 2022 — $0)	465		462

TOTAL LIABILITIES	15,265		16,826
COMMITMENTS AND CONTINGENCIES

REDEEMABLE NONCONTROLLING INTERESTS	—		168

SHAREHOLDERS’ EQUITY

Ordinary Shares (par value $1 each, issued and outstanding 2023: 15,196,685; 2022: 17,588,050):
Voting Ordinary Shares (issued and outstanding 2023: 15,196,685; 2022: 15,990,338)	15		16

Non-voting convertible ordinary Series C Shares (issued and outstanding 2023: 0; 2022: 1,192,941)	—		1
Non-voting convertible ordinary Series E Shares (issued and outstanding 2023: 0; 2022: 404,771)	—		—
Preferred Shares:
Series C Preferred Shares (issued and held in treasury 2023 and 2022: 388,571)	—		—
Series D Preferred Shares (issued and outstanding 2023 and 2022: 16,000; liquidation preference $400)	400		400
Series E Preferred Shares (issued and outstanding 2023 and 2022: 4,400; liquidation preference $110)	110		110
Treasury shares, at cost (Series C Preferred shares 2023 and 2022: 388,571)	(422)		(422)
Joint Share Ownership Plan (voting ordinary shares, held in trust 2023 and 2022: 565,630)	(1)		(1)
Additional paid-in capital	579		766
Accumulated other comprehensive loss	(336)		(302)
Retained earnings	5,190		4,406
Total Enstar Shareholders’ Equity	5,535		4,974
Noncontrolling interests	113		186
TOTAL SHAREHOLDERS’ EQUITY	5,648		5,160
TOTAL LIABILITIES, REDEEMABLE NONCONTROLLING INTERESTS AND SHAREHOLDERS’ EQUITY	$	20,913	$	22,154

Enstar Group Limited | 2023 Press Release 12

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.

Some of the adjustments reflected in our non-GAAP measures are recurring items, such as the exclusion of adjustments to net realized and unrealized (gains)/losses on fixed maturity investments recognized in our income statement, the fair value of certain of our loss reserve liabilities for which we have elected the fair value option, and the amortization of fair value adjustments.

Management makes these adjustments in assessing our performance so that the changes in fair value due to interest rate movements, which are applied to some but not all of our assets and liabilities as a result of preexisting accounting elections, do not impair comparability across reporting periods.

It is important for the readers of our periodic filings to understand that these items will recur from period to period.

However, we exclude these items for the purpose of presenting a comparable view across reporting periods of the impact of our underlying claims management and investments without the effect of interest rate fluctuations on assets that we anticipate to hold to maturity and non-cash changes to the fair value of our reserves.

Similarly, our non-GAAP measures reflect the exclusion of certain items that we deem to be nonrecurring, unusual or infrequent when the nature of the charge or gain is such that it is not reasonably likely that such item may recur within two years, nor was there a similar charge or gain in the preceding two years. This includes adjustments related to bargain purchase gains on acquisitions of businesses, net gains or losses on sales of subsidiaries, net assets of held for sale or disposed subsidiaries classified as discontinued operations and other items that we separately disclose.

The following table presents more information on each non-GAAP measure. The results and GAAP reconciliations for these measures are set forth further below.

Non-GAAP Measure

Definition

Purpose of Non-GAAP Measure over GAAP Measure

Fully diluted 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 the exercise of equity awards granted but not yet vested as, over the long term, this presents both management and investors with a more economically accurate measure of the realizable value of shareholder returns by factoring in the impact of share dilution.

We use this non-GAAP measure in our incentive compensation program.

Enstar Group Limited | 2023 Press Release 13

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 consistent measure of the performance of our business by enabling comparison between the financial periods presented.

We eliminate the impact of net realized and unrealized (gains) losses on fixed maturities and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as:

•we typically hold most of our fixed maturities until the earlier of maturity or the time that they are used to fund any settlement of related liabilities which are generally recorded at cost; and

•removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option.

Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods.

We include fair value adjustments as non-GAAP adjustments to the adjusted operating income (loss) attributable to Enstar ordinary shareholders as they are non-cash charges that are not reflective of the impact of our claims management strategies on our loss portfolios.

We eliminate the net gain (loss) on the purchase and sales of subsidiaries and net income from discontinued operations, as these items are not indicative of our ongoing operations.

We use this non-GAAP measure in our incentive compensation program.

Adjusted operating income (loss) attributable to Enstar ordinary shareholders

(numerator)

Net income (loss) attributable to Enstar ordinary shareholders, adjusted for:

-net realized and unrealized (gains) losses on fixed maturities 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 income from discontinued operations (if any),

-tax effects of adjustments, and

-adjustments attributable to noncontrolling interests

Adjusted opening Enstar ordinary shareholders' equity (denominator)

Opening Enstar ordinary shareholders' equity, less:

-net unrealized gains (losses) on fixed maturities 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)

Enstar Group Limited | 2023 Press Release 14

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 and comparable measurement of the impact of our claims management strategies on our loss portfolios across acquisition years and also to our overall financial periods.

We use this measure to evaluate the impact of our claims management strategies because it provides visibility into our ability to settle our claims obligations for amounts less than our initial estimate at the point of acquiring the obligations.

The following components of periodic recurring net incurred losses and LAE and net loss reserves are not considered key components of our claims management performance for the following reasons:

•Prior to the settlement of the contractual arrangements, the results of our Legacy Underwriting segment were economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement(2); as such, the results were not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies;

•The results of our Assumed Life segment relate only to our prior exposure to active property catastrophe business; as this business was not in run-off, the results were not a relevant contribution to Adjusted RLE;

•The change in fair value of insurance contracts for which we have elected the fair value option(1) has been removed to support comparability between the two acquisition years for which we elected the fair value option in reserves assumed and the acquisition years for which we did not make this election (specifically, this election was only made in the 2017 and 2018 acquisition years and the election of such option is irrevocable); and

•The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis.

We include our performance in managing claims and estimated future expenses on our defendant A&E liabilities because such performance is relevant to assessing our claims management strategies even though such liabilities are not included within the loss reserves.

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 Assumed Life operations

-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 net ultimate liabilities and reduction in estimated future expenses of our defendant A&E liabilities.

Adjusted net loss reserves

(denominator)

Net losses and LAE, adjusted to:

Remove:

-Legacy Underwriting and Assumed Life net loss reserves

-current period net loss reserves

-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 A&E liability exposures and estimated future expenses.

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.

We adjust our investment returns to eliminate the impact of the change in fair value of fixed maturities (both credit spreads and interest rates), as we typically hold most of these investments 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 maturities and funds held-directly managed; and

-unrealized (gains) losses on fixed maturities, AFS included within OCI, net of reclassification adjustments and excluding foreign exchange.

Adjusted average aggregate total investable assets (denominator)

Total average investable assets, adjusted for:

-net unrealized (gains) losses on fixed maturities, AFS included within AOCI

-net unrealized (gains) losses on fixed maturities, trading

(1) Comprises the discount rate and risk margin components.

(2) The reinsurance contractual arrangements (including the Capacity Lease Agreement) were settled during the second quarter of 2023. As a result of the settlement, we did not record any transactions in the Legacy Underwriting segment in 2023.

Enstar Group Limited | 2023 Press Release 15

Reconciliation of GAAP to Non-GAAP Measures

The table below presents a reconciliation of BVPS to Fully Diluted BVPS*:



	December 31, 2023					December 31, 2022					December 31, 2021
	Equity (1)		Ordinary Shares	Per Share Amount		Equity (1) (2)		Ordinary Shares	Per Share Amount		Equity (1)		Ordinary Shares	Per Share Amount
	(in millions of U.S. dollars, except share and per share data)
Book value per ordinary share	$	5,025	14,631,055	$	343.45	$	4,464	17,022,420	$	262.24	$	5,813	17,657,944	$	329.20
Non-GAAP adjustment:

Share-based compensation plans			292,190					218,171					315,205

Fully diluted book value per ordinary share*	$	5,025	14,923,245	$	336.72	$	4,464	17,240,591	$	258.92	$	5,813	17,973,149	$	323.43

(1) Equity comprises Enstar ordinary shareholders' equity, which is calculated as Enstar shareholders' equity less preferred shares ($510 million as of each of December 31, 2023, 2022 and 2021) prior to any non-GAAP adjustments.

(2) Enstar ordinary shareholders’ equity as of December 31, 2022 has been retrospectively adjusted by $273 million for the impact of adopting ASU 2018-12.

*Non-GAAP measure.

The tables below present a reconciliation of ROE to Adjusted ROE*:


	Three Months Ended
	December 31, 2023						December 31, 2022
	Net (loss) earnings (1)		Opening equity (1)		(Adj) ROE			Net (loss) earnings (1)		Opening equity (1)(7)		(Adj) ROE
	(in millions of U.S. dollars)
Net income/Opening equity/ROE (1)	$	599	$	4,367	13.7	%		$	227	$	4,099	5.5	%
Non-GAAP adjustments for loss (gains):

Net realized losses (gains) on fixed maturities, AFS (2) / Net unrealized losses (gains) on fixed maturities, AFS (3)	10		634					23		757
Net unrealized (gains) losses on fixed maturities, trading (2) / Net unrealized losses (gains) on fixed maturities, trading (3)	(108)		366					(53)		530
Net unrealized (gains) losses on funds held - directly managed (2) / Net unrealized losses (gains) on funds held - directly managed (3)	(96)		222					50		639
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 (4)	54		(292)					28		(305)

Amortization of fair value adjustments / Fair value adjustments	4		(112)					(29)		(95)


Tax effects of adjustments (5)	5		—					(1)		—
Adjustments attributable to noncontrolling interests (6)	—		—					(21)		—
Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE*	$	468	$	5,185	9.0	%		$	224	$	5,625	4.0	%

(1) Net income (loss) comprises net income (loss) 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 as of each of September 30, 2023 and 2022), prior to any non-GAAP adjustments.

(2) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations.

(3) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance.

(4) Comprises the discount rate and risk margin components.

(5) 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.

(6) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interest associated with the specific subsidiaries to which the adjustments relate.

(7) Enstar ordinary shareholders’ equity as of September 30, 2022 has been retrospectively adjusted by $236 million for the impact of adopting ASU 2018-12.

*Non-GAAP measure.

Enstar Group Limited | 2023 Press Release 16


	Year Ended
	December 31, 2023						December 31, 2022					December 31, 2021
	Net income (loss)(1)		Opening equity (1)(2)		(Adj) ROE			Net income (loss) (1)		Opening equity (1)		(Adj) ROE		Net income (loss) (1)		Opening equity (1)		(Adj) ROE
	(in millions of U.S. dollars)
Net income (loss)/Opening equity/ROE (1)	$	1,082	$	4,464	24.2	%		$	(906)	$	5,813	(15.6)	%	$	502	$	6,326	7.9	%
Non-GAAP adjustments for loss (gains):


Net realized losses (gains) on fixed maturities, AFS (3) / Net unrealized losses (gains) on fixed maturities, AFS (4)	65		647					111		36				4		(82)
Net unrealized (gains) losses on fixed maturities, trading (3) / Net unrealized losses (gains) on fixed maturities, trading (4)	(84)		400					503		(134)				144		(384)
Net unrealized (gains) losses on funds held - directly managed (3) / Net unrealized losses (gains) on funds held - directly managed (4)	(47)		780					567		9				62		(94)
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 (5)	78		(294)					(200)		(107)				(75)		(33)

Amortization of fair value adjustments / Fair value adjustments	17		(124)					(18)		(106)				16		(128)
Net gain on purchase and sales of subsidiaries	—		—					—		—				(73)		—

Tax effects of adjustments (6)	(7)		—					(7)		—				(21)		—
Adjustments attributable to noncontrolling interests (7)	(2)		—					(111)		—				6		—

Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE*	$	1,102	$	5,873	18.8	%		$	(61)	$	5,511	(1.1)	%	$	565	$	5,605	10.1	%

(1) Net income (loss) comprises net income (loss) 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 as of each of December 31, 2022, 2021 and 2020), prior to any non-GAAP adjustments.

(2) Enstar ordinary shareholders’ equity as of December 31, 2022 has been retrospectively adjusted by $273 million for the impact of adopting ASU 2018-12.

(3) Net realized gains (losses) on fixed maturities, AFS and funds held - directly managed are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations.

(4) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance.

(5) Comprises the discount rate and risk margin components.

(6) 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.

(7) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interest associated with the specific subsidiaries to which the adjustments relate.

*Non-GAAP measure.

Enstar Group Limited | 2023 Press Release 17

The tables below present a reconciliation of PPD to Adjusted PPD* and RLE to Adjusted RLE*:


	Year Ended		As of						Year Ended
	December 31, 2023		December 31, 2023		December 31, 2022		December 31, 2023		December 31, 2023
	RLE/PPD		Net loss reserves		Net loss reserves		Average net loss reserves		RLE %
	(in millions of U.S. dollars)
PPD/net loss reserves/RLE %	$	131	$	11,585	$	12,011	$	11,798	1.1	%
Non-GAAP adjustments for expenses (income):

Legacy Underwriting	—		—		(139)		(69)
Net loss reserves incurred in the current period	—		(30)		—		(15)




Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies	17		107		124		116
Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1)	78		246		294		270
Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities	(1)		527		572		550
Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E	2		33		35		34
Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %*	$	227	$	12,468	$	12,897	$	12,684	1.8	%

*Non-GAAP measure.


	Year Ended		As of						Year Ended
	December 31, 2022		December 31, 2022		December 31, 2021		December 31, 2022		December 31, 2022
	PPD		Net loss reserves		Net loss reserves		Average net loss reserves		RLE %
	(in millions of U.S. dollars)
PPD/net loss reserves/RLE %	$	756	$	12,011	$	11,926	$	11,969	6.3	%
Non-GAAP adjustments for expenses (income):
Assumed Life	(55)		—		(181)		(91)
Legacy Underwriting	3		(135)		(153)		(144)
Net loss reserves incurred in the current period	—		(45)		—		(23)


Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies	(18)		124		106		115
Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1)	(200)		294		107		201
Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities	2		572		573		573
Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E	1		35		37		37
Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %*	$	489	$	12,856	$	12,415	$	12,637	3.9	%

*Non-GAAP measure.

Enstar Group Limited | 2023 Press Release 18


	Year Ended		As of						Year Ended
	December 31, 2021		December 31, 2021		December 31, 2020		December 31, 2021		December 31, 2021
	PPD		Net loss reserves		Net loss reserves		Average net loss reserves		RLE %
	(in millions of U.S. dollars)
PPD/Net loss reserves/RLE %	$	403	$	11,926	$	8,763	$	10,344	3.9	%
Non-GAAP adjustments for expenses (income):
Net loss reserves incurred in the current period	—		(143)		—		(72)
Legacy Underwriting	(6)		(140)		(955)		(548)
Assumed Life	—		(179)		—		(90)


Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies	16		106		128		117
Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1)	(75)		107		33		70
Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities	38		573		615		594
Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E	5		37		43		40
Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %*	$	381	$	12,287	$	8,627	$	10,455	3.6	%

(1) Comprises the discount rate and risk margin components.

*Non-GAAP measure.

Enstar Group Limited | 2023 Press Release 19

The tables below present a reconciliation of our TIR to our Adjusted TIR*:


	For the Three Months Ended December 31,						For the Year Ended December 31,
	2023			2022			2023			2022			2021

Investment results
Net investment income	$	176		$	153		$	647		$	455		$	312
Net realized (losses) gains	(10)			(23)			(65)			(111)			(61)
Net unrealized gains (losses)	306			38			528			(1,503)			178
(Losses) income from equity method investments	(9)			(86)			13			(74)			93
Other comprehensive income:
Unrealized gains (losses) on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange	220			87			222			(570)			(100)
TIR ($)	$	683		$	169		$	1,345		$	(1,803)		$	422

Non-GAAP adjustments:
Net realized and unrealized (gains) losses on fixed maturities, AFS and trading and funds held-directly managed	(194)			20			(66)			1,181			210
Unrealized (gains) losses on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange	(220)			(87)			(222)			570			100

Adjusted TIR ($)*	$	269		$	102		$	1,057		$	(52)		$	732

Total investments	17,413			18,210			17,413			18,210			$	19,616
Cash and cash equivalents, including restricted cash and cash equivalents	830			1,330			830			1,330			2,092


Total investable assets	$	18,243		$	19,540		$	18,243		$	19,540		$	21,708


Average aggregate invested assets, at fair value (1)	$	18,472		$	19,503		$	18,607		$	20,079		$	20,840
Annualized TIR % (2)	14.8		%	3.5		%	7.2		%	(9.0)		%	2.0		%

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	725			1,827			725			1,827			(89)
Adjusted investable assets*	$	18,968		$	21,367		$	18,968		$	21,367		$	21,619


Adjusted average aggregate invested assets, at fair value (3)	$	19,445		$	21,380		$	19,769		$	21,165		$	20,561
Annualized adjusted TIR %* (4)	5.5		%	1.9		%	5.3		%	(0.2)		%	3.6		%

(1) This amount is a two period average of the total investable assets for the three months ended December 31, 2023 and 2022, respectively, and a five period average for the years ended December 31, 2023, 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 period average of the adjusted investable assets* for the three months ended December 31, 2023 and 2022, respectively, and a five period average for the years ended December 31, 2023, 2022 and 2021, respectively, as presented above.

(4) Annualized adjusted TIR %* is calculated by dividing annualized adjusted TIR* ($) by adjusted average aggregate invested assets, at fair value*.

*Non-GAAP measure.

Enstar Group Limited | 2023 Press Release 20

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement December 31, 2023 ENSTAR GROUP LIMITED

| enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Book Value Per Share & Return On Equity 7 Consolidated Results by Segment 8 Prior Period Development (“PPD”) by Acquisition Year 12 Ultimate Losses % Acquired Losses by Acquisition Year 13 Adjusted PPD by Acquisition Year 14 Adjusted Ultimate Losses % Acquired Losses 15 Capital Position & Credit Ratings 16 Non-GAAP Measures 17 Reconciliation to Fully Diluted Book Value per Share 19 Reconciliation to Adjusted Return on Equity 20 Reconciliation to Adjusted Run-off Liability Earnings 23 Reconciliation to Adjusted Total Investment Return 26 Reconciliation of PPD by Acquisition Year 27 Reconciliation of Assumed and Acquired Reserves 29 Investment Composition 30

| enstargroup.com 3 Explanatory Notes About Enstar Enstar is a NASDAQ-listed leading global (re)insurance group that offers capital release solutions through its network of group companies in Bermuda, the United States, the United Kingdom, Continental Europe and Australia. A market leader in completing legacy acquisitions, Enstar has acquired over 115 companies and portfolios since its formation. 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. 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. Some of the adjustments reflected in our non-GAAP measures are recurring items, such as the exclusion of adjustments to net realized and unrealized (gains)/losses on fixed maturities recognized in our statements of operations, the fair value of certain of our loss reserve liabilities for which we have elected the fair value option, and the amortization of fair value adjustments. Management makes these adjustments in assessing our performance so that the changes in fair value due to interest rate movements, which are applied to some but not all of our assets and liabilities as a result of preexisting accounting elections, do not impair comparability across reporting periods. It is important for the readers of our periodic filings to understand that these items will recur from period to period. However, we exclude these items for the purpose of presenting a comparable view across reporting periods of the impact of our underlying claims management and investments without the effect of interest rate fluctuations on assets that we anticipate to hold to maturity and non-cash changes to the fair value of our reserves. Similarly, our non-GAAP measures reflect the exclusion of certain items that we deem to be nonrecurring, unusual or infrequent when the nature of the charge or gain is such that it is not reasonably likely that such item may recur within two years, nor was there a similar charge or gain in the preceding two years. This includes adjustments related to bargain purchase gains on acquisitions of businesses, net gains or losses on sales of subsidiaries, net assets of held for sale or disposed subsidiaries classified as discontinued operations, and other items that we separately disclose. Refer to pages 17 to 26 for further details.

4 Explanatory Notes (continued) Investment Composition In certain instances, U.S. GAAP requires, in part, that invested assets be classified based upon the legal form of the investment which may not correspond to management’s view of the underlying economic exposure. For example: 1. Enstar has certain investments in public shares of exchange traded funds (“ETFs”) where the underlying exposure of the ETF is investment grade fixed income securities, and Enstar also has certain privately held equities which management evaluates based on the underlying economic exposures. U.S. GAAP requires that these investments be classified as “Equities”. 2. Enstar has certain private equity funds that are collectively held in a limited partnership, which management evaluates based on the nature of the underlying investments within these funds. U.S. GAAP requires that the investment be classified as “Private equity funds” within “Other Investments”. Where relevant, we have disclosed the underlying economic exposure of our investments in order to be consistent with the manner in which management views the underlying portfolio composition. Refer to pages 30 and 31 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 filings with the Securities and Exchange Commission, including our Annual Reports on Form 10-K and our Quarterly Reports on Form 10- Q. 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 5 Three Months Ended Year Ended December 31, 2023 December 31, 2022 December 31, 2023 December 31, 2022 Key Income Metrics ROE 13.7 % 5.5 % 24.2 % (15.6) % Adjusted ROE (1) 9.0 % 4.0 % 18.8 % (1.1) % Basic net earnings (loss) per share $ 40.14 $ 13.34 $ 69.22 $ (52.65) Diluted net earnings (loss) per share $ 39.71 $ 13.26 $ 68.47 $ (52.65) Key Run-off Metrics Average net loss reserves $ 11,798 $ 11,969 Run-off liability earnings (“RLE”) 1.1 % 6.3 % Average adjusted net loss reserves (1) $ 12,684 $ 12,637 Adjusted RLE (1) 1.8 % 3.9 % Key Investment Return Metrics Average aggregate invested assets $ 18,472 $ 19,503 $ 18,607 $ 20,079 Annualized total investment return (“TIR”) 14.8 % 3.5 % 7.2 % (9.0) % Annualized investment book yield 4.00 % 3.33 % 3.86 % 2.47 % (Losses) earnings from equity method investments $ (9) $ (86) $ 13 $ (74) Adjusted average aggregate invested assets (1) $ 19,445 $ 21,380 $ 19,769 $ 21,165 Annualized adjusted TIR (1) 5.5 % 1.9 % 5.3 % (0.2) % Share Repurchases Ordinary shares repurchased: Shares 841,735 — 2,439,447 697,580 Cost $ 191 $ — $ 532 $ 163 Average price per share $ 227.18 $ — $ 217.98 $ 233.92 As of December 31, 2023 December 31, 2022 Key Shareholder Metrics Ordinary shareholder’s equity $ 5,025 $ 4,464 Total Enstar shareholders’ equity $ 5,535 $ 4,974 Book value per ordinary share (“BVPS”) $ 343.45 $ 262.24 Fully diluted BVPS (“FDBVPS”) (1) $ 336.72 $ 258.92 Change in FDBVPS 30.0 % (19.9) % Total ordinary shares outstanding 14,631,055 17,022,420 Fully diluted ordinary shares outstanding 14,923,245 17,240,591 Key Balance Sheet Metrics Total assets $ 20,913 $ 22,154 Debt obligations $ 1,831 $ 1,829 Total liabilities $ 15,265 $ 16,826 Total investable assets to ordinary shareholders’ equity 3.63x 4.38x Total net loss reserves to ordinary shareholders’ equity 2.31x 2.69x Debt to total capitalization attributable to Enstar 24.9 % 26.9 % Financial Highlights (1) Non-GAAP financial measure, refer to pages 17 to 26 for explanatory notes and a reconciliation to the most directly comparable GAAP measure.

| enstargroup.com 6 Year Ended December 31, 2023 December 31, 2022 December 31, 2021 December 31, 2020 December 31, 2019 (2) Key Income Metrics Return on equity 24.2 % (15.6) % 7.9 % 38.4 % 25.5 % Adjusted return on equity (1) 18.8 % (1.1) % 10.1 % 41.9 % 18.8 % Key Run-off Metrics Average net loss reserves $ 11,798 $ 11,969 $ 10,344 $ 8,352 $ 7,641 Run-off liability earnings 1.1 % 6.3 % 3.9 % 0.4 % 0.1 % Average adjusted net loss reserves (1) $ 12,684 $ 12,637 $ 10,455 $ 8,129 $ 7,160 Adjusted run-off liability earnings (1) 1.8 % 3.9 % 3.6 % 3.5 % 4.0 % Key Investment Return Metrics Average investable assets $ 18,607 $ 20,079 $ 20,840 $ 15,443 $ 13,758 Total investment return 7.2 % (9.0) % 2.0 % 14.6 % 10.0 % Investment book yield 3.86 % 2.47 % 1.84 % 2.53 % 2.80 % Income (losses) from equity method investments $ 13 $ (74) $ 93 $ 239 $ 56 Average adjusted investable assets (1) $ 19,769 $ 21,165 $ 20,561 $ 15,153 $ 13,646 Adjusted total investment return (1) 5.3 % (0.2) % 3.6 % 12.4 % 6.3 % Key Shareholder Metrics Ordinary shareholders’ equity $ 5,025 $ 4,464 $ 5,813 $ 6,326 $ 4,490 Total Enstar shareholders’ equity $ 5,535 $ 4,974 $ 6,323 $ 6,836 $ 5,000 Basic book value per ordinary share $ 343.45 $ 262.24 $ 329.20 $ 293.97 $ 208.73 Fully diluted book value per ordinary share (1) $ 336.72 $ 258.92 $ 323.43 $ 288.56 $ 205.11 Change in fully diluted book value per ordinary share 30.0 % (19.9) % 12.1 % 40.7 % 25.9 % Ordinary shares repurchased: Shares 2,439,447 697,580 4,010,695 178,280 — Cost $ 532 $ 163 $ 942 $ 26 $ — Average price per share $ 217.98 $ 233.92 $ 234.82 $ 145.87 $ — Total ordinary shares outstanding 14,631,055 17,022,420 17,657,944 21,519,602 21,511,505 Fully diluted ordinary shares outstanding 14,923,245 17,240,591 17,973,149 21,993,598 21,989,971 Key Balance Sheet Metrics Total assets $ 20,913 $ 22,154 $ 24,656 $ 21,789 $ 19,984 Debt obligations $ 1,831 $ 1,829 $ 1,691 $ 1,373 $ 1,191 Total liabilities $ 15,265 $ 16,826 $ 17,924 $ 14,574 $ 14,531 Total investable assets to ordinary shareholders’ equity 3.63x 4.38x 3.73x 2.73x 3.13x Total net loss reserves to ordinary shareholders’ equity 2.31x 2.69x 2.05x 1.39x 1.77x Debt to total capitalization attributable to Enstar 24.9 % 26.9 % 21.1 % 16.7 % 19.2 % Financial Highlights - Five Years (1) Non-GAAP financial measure, refer to pages 17 to 26 for explanatory notes and a reconciliation to the most directly comparable GAAP measure. (2) The 2018 balance sheet has not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification.

| enstargroup.com 7 Book Value Per Share & Return on Equity - Five Years Growth in Book Value Per Ordinary Share and Fully Diluted Book Value Per Ordinary Share* Annual % Change $208.73 $293.97 $329.20 $262.24 $343.45 $205.11 $288.56 $323.43 $258.92 $336.72 Book Value Per Ordinary Share Fully Diluted Book Value Per Ordinary Share* 2019 2020 2021 2022 2023 $0 $50 $100 $150 $200 $250 $300 $350 $400 Return on Equity and Adjusted Return on Equity* 25.5% 38.4% 7.9% (15.6)% 24.2% 18.8% 41.9% 10.1% (1.1)% 18.8% Return on Equity Adjusted Return on Equity* 2019 2020 2021 2022 2023 40.8% 40.7% 12.0% 12.1% (20.3)% (19.9)% 31.0% 30.0% 26.3% 25.9% * Non-GAAP financial measure, refer to page 17 for further details. See also pages 19, 21 and 22 for a reconciliation to the most directly comparable GAAP measure.

| enstargroup.com 8 Consolidated Results by Segment - Q4 2023 Three Months Ended December 31, 2023 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total REVENUES Net premiums earned $ 14 $ — $ — $ — $ — $ 14 Net investment income — — 176 — — 176 Net realized losses — — (10) — — (10) Net unrealized gains — — 306 — — 306 Other income (expense) (1) 1 — — (4) (4) Total revenues 13 1 472 — (4) 482 EXPENSES Net incurred losses and loss adjustment expenses Current period 12 — — — — 12 Prior period (154) — — — 58 (96) Total net incurred losses and loss adjustment expenses (142) — — — 58 (84) Amortization of net deferred charge assets — — — — 31 31 Acquisition costs 4 — — — — 4 General and administrative expenses 47 — 10 — 47 104 Total expenses (91) — 10 — 136 55 INCOME (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 104 1 462 — (140) 427 Losses from equity method investments — — (9) — — (9) SEGMENT INCOME (LOSS) $ 104 $ 1 $ 453 $ — (140) 418 Interest expense (23) (23) Net foreign exchange losses (24) (24) Income tax benefit 238 238 NET INCOME 609 Net income attributable to noncontrolling interests (1) (1) NET INCOME ATTRIBUTABLE TO ENSTAR 608 Dividends on preferred shares (9) (9) NET INCOME ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ 41 $ 599 (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 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.

| enstargroup.com 9 Consolidated Results by Segment - Q4 2022 Three Months Ended December 31, 2022 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total REVENUES Net premiums earned $ 13 $ — $ — $ 1 $ — $ 14 Net investment income — — 151 2 — 153 Net realized losses — — (23) — — (23) Net unrealized gains — — 36 2 — 38 Other income (expense) 3 — — (3) 2 2 Total revenues 16 — 164 2 2 184 EXPENSES Net incurred losses and loss adjustment expenses Current period 9 — — — — 9 Prior period (254) (26) — 1 (1) (280) Total net incurred losses and loss adjustment expenses (245) (26) — 1 (1) (271) Amortization of net deferred charge assets — — — — 20 20 Acquisition costs 4 — — (1) — 3 General and administrative expenses 20 1 11 2 63 97 Total expenses (221) (25) 11 2 82 (151) INCOME (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 237 25 153 — (80) 335 Losses from equity method investments — — (86) — — (86) SEGMENT INCOME (LOSS) $ 237 $ 25 $ 67 $ — (80) 249 Interest expense (18) (18) Net foreign exchange losses (12) (12) Income tax benefit 16 16 NET INCOME 235 Net loss attributable to noncontrolling interests 1 1 NET INCOME ATTRIBUTABLE TO ENSTAR 236 Dividends on preferred shares (9) (9) NET (LOSS) INCOME ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (102) $ 227 (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 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.

| enstargroup.com 10 Consolidated Results by Segment - 2023 Year Ended December 31, 2023 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total REVENUES Net premiums earned $ 43 $ — $ — $ — $ — $ 43 Net investment income — — 647 — — 647 Net realized losses — — (65) — — (65) Net unrealized gains — — 528 — — 528 Other income (expense) 10 277 — — (11) 276 Total revenues 53 277 1,110 — (11) 1,429 EXPENSES Net incurred losses and loss adjustment expenses Current period 30 — — — — 30 Prior period (226) — — — 95 (131) Total net incurred losses and loss adjustment expenses (196) — — — 95 (101) Amortization of net deferred charge assets — — — — — 106 106 Acquisition costs 10 — — — — 10 General and administrative expenses 177 — 43 — 149 369 Total expenses (9) — 43 — 350 384 INCOME (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 62 277 1,067 — (361) 1,045 Income from equity method investments — — 13 — — 13 SEGMENT INCOME (LOSS) $ 62 $ 277 $ 1,080 $ — (361) 1,058 Interest expense (90) (90) Net foreign exchange gains — — Income tax benefit 250 250 NET INCOME 1,218 Net income attributable to noncontrolling interests (100) (100) NET INCOME ATTRIBUTABLE TO ENSTAR 1,118 Dividends on preferred shares (36) (36) NET (LOSS) INCOME ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (337) $ 1,082 (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 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.

| enstargroup.com 11 Consolidated Results by Segment - 2022 Year Ended December 31, 2022 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total REVENUES Net premiums earned $ 40 $ 17 $ — $ 9 $ — $ 66 Net investment income — — 445 10 — 455 Net realized losses — — (111) — — (111) Net unrealized losses — — (1,493) (10) — (1,503) Other income 22 — — 1 12 35 Total revenues 62 17 (1,159) 10 12 (1,058) EXPENSES Net incurred losses and loss adjustment expenses Current period 44 — — 4 — 48 Prior period (486) (55) — 3 (218) (756) Total net incurred losses and loss adjustment expenses (442) (55) — 7 (218) (708) Policyholder benefit expenses — 25 — — — 25 Amortization of net deferred charge assets — — — — 80 80 Acquisition costs 22 — — 1 — 23 General and administrative expenses 143 7 37 2 142 331 Total expenses (277) (23) 37 10 4 (249) INCOME (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 339 40 (1,196) — 8 (809) Losses from equity method investments — — (74) — — (74) SEGMENT INCOME (LOSS) $ 339 $ 40 $ (1,270) $ — 8 (883) Interest expense (89) (89) Net foreign exchange gains 15 15 Income tax benefit 12 12 NET LOSS (945) Net loss attributable to noncontrolling interests 75 75 NET LOSS ATTRIBUTABLE TO ENSTAR (870) Dividends on preferred shares (36) (36) NET LOSS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $ (15) $ (906) (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 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.

| enstargroup.com 12 Prior Period Development (“PPD”) by Acquisition year PPD in Year Ended December 31, Acquisition Year 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (unaudited) 2013 and prior $ 289 $ 282 $ 160 $ 133 $ 107 $ 86 $ 60 $ 43 $ 14 $ 11 2014(1) 30 18 18 34 (112) (110) 1 25 30 21 2015 87 301 42 79 28 20 21 12 15 2016 9 (34) 18 9 21 10 14 19 2017 84 98 (84) (50) 89 183 (89) 2018 33 42 18 45 58 (12) 2019 33 33 47 59 (37) 2020 (71) (27) (120) (21) 2021 150 435 179 2022 71 78 2023 (33) 319 387 488 259 223 4 32 403 756 131 Acquisition Year Cumulative PPD in Year Ended December 31, 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (unaudited) 2013 and prior $ 289 $ 571 $ 731 $ 864 $ 971 $ 1,057 $ 1,117 $ 1,160 $ 1,174 $ 1,185 2014(1) 30 48 66 100 (12) (122) (121) (96) (66) (45) 2015 87 388 430 509 537 557 578 590 605 2016 9 (25) (7) 2 23 33 47 66 2017 84 182 98 48 137 320 231 2018 33 75 93 138 196 184 2019 33 66 113 172 135 2020 (71) (98) (218) (239) 2021 150 585 764 2022 71 149 2023 (33) (1) The 2014 acquisition year includes losses relating to our StarStone business when this business was actively managed within our Legacy Underwriting segment.

| enstargroup.com 13 Ultimate Losses % Acquired Losses by Acquisition Year Ultimate Losses for the Years Ended December 31, Assumed and Acquired net losses and LAE Acquisition Year Third Party Related Party and Transfers Between Acquisition Years Total 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (Unaudited) 2013 and prior(1) $ 3,592 $ — $ 3,592 $ 3,303 $ 3,021 $ 2,861 $ 2,728 $ 2,621 $ 2,535 $ 2,475 $ 2,432 $ 2,418 $ 2,407 2014 1,057 — 1,057 1,027 1,009 991 957 1,069 1,179 1,178 1,153 1,123 1,102 2015 1,756 — 1,756 1,669 1,368 1,326 1,247 1,219 1,199 1,178 1,166 1,151 2016 1,357 — 1,357 1,348 1,382 1,364 1,355 1,334 1,324 1,310 1,291 2017 1,536 — 1,536 1,452 1,354 1,438 1,488 1,399 1,216 1,305 2018 2,757 — 2,757 2,724 2,682 2,664 2,619 2,561 2,573 2019 1,817 — 1,817 1,784 1,751 1,704 1,645 1,682 2020(2) 2,191 (782) 1,409 1,480 1,507 1,627 1,648 2021(3) 3,710 840 4,550 4,400 3,965 3,786 2022(2) 2,649 782 3,431 3,360 3,282 2023 2,215 — 2,215 2,248 Ultimate Losses as a Percentage of Assumed and Acquired Net Loss Reserves Acquisition Year At End of Year of Acquisition Years thereafter: One Two Three Four Five Six Seven Eight Nine Ten (Unaudited) 2013 and prior 100 % 92 % 84 % 80 % 76 % 73 % 71 % 69 % 68 % 67 % 67 % 2014(4) 97 % 95 % 94 % 91 % 101 % 112 % 111 % 109 % 106 % 104 % 2015 95 % 78 % 76 % 71 % 69 % 68 % 67 % 66 % 66 % 2016 99 % 102 % 101 % 100 % 98 % 98 % 97 % 95 % 2017 95 % 88 % 94 % 97 % 91 % 79 % 85 % 2018 99 % 97 % 97 % 95 % 93 % 93 % 2019 98 % 96 % 94 % 91 % 93 % 2020 105 % 107 % 115 % 117 % 2021 97 % 87 % 83 % 2022 98 % 96 % 2023 101 % (1) For the 2013 and prior acquisition years, the net reserves shown are as at December 31, 2012, and are not the net reserves assumed and acquired. (2) $782 million of Assumed and Acquired net losses and LAE relating to the Aspen ADC have been transferred from the 2020 to the 2022 acquisition year. Any PPD on this portfolio that occurred in the years ended December 31 2021 and 2020 has not been reclassified between periods. (3) 2021 Assumed and Acquired net losses and LAE - Related Party of $840 million relates to the acquisition of Enhanzed Re. (4) The 2014 acquisition year includes losses relating to our StarStone business when this business was actively managed within our Legacy Underwriting segment.

| enstargroup.com 14 Adjusted PPD by Acquisition Year* Adjusted PPD* in Year Ended December 31, Acquisition Year 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (Unaudited) 2013 and prior $ 291 $ 275 $ 171 $ 126 $ 108 $ 92 $ 60 $ 42 $ 29 $ 13 2014 2 (37) 1 1 8 5 3 30 15 (7) 2015 92 306 45 81 30 21 22 13 16 2016 9 (37) 41 16 36 8 22 22 2017 114 87 — 39 34 30 (37) 2018 50 109 69 38 19 25 2019 33 130 92 54 (39) 2020 (71) (27) (120) (21) 2021 142 356 210 2022 71 78 2023 (33) $ 293 $ 330 $ 487 $ 249 $ 375 $ 285 $ 287 $ 381 $ 489 $ 227 Acquisition Year Cumulative Adjusted PPD* in Year Ended December 31, 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (Unaudited) 2013 and prior $ 291 $ 566 $ 737 $ 863 $ 971 $ 1,063 $ 1,123 $ 1,165 $ 1,194 $ 1,207 2014 2 (35) (34) (33) (25) (20) (17) 13 28 21 2015 92 398 443 524 554 575 597 610 626 2016 9 (28) 13 29 65 73 95 117 2017 114 201 201 240 274 304 267 2018 50 159 228 266 285 310 2019 33 163 255 309 270 2020 (71) (98) (218) (239) 2021 142 498 708 2022 71 149 2023 (33) * Non-GAAP financial measure. Refer to explanatory notes on pages 17 and 18 for further details. See also pages 27 and 28 for a reconciliation to the most directly comparable GAAP measure.

| enstargroup.com 15 Adjusted Ultimate Losses % Acquired Losses* Adjusted Assumed and Acquired net losses and LAE* Adjusted Ultimate Losses* for the Years Ended December 31, (1) Acquisition Year Third Party Related Party and Transfers Between Acquisition Years Total 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) (Unaudited) 2013 and prior(1) $ 3,576 $ — $ 3,576 $ 3,285 $ 3,010 $ 2,839 $ 2,713 $ 2,605 $ 2,513 $ 2,453 $ 2,411 $ 2,382 $ 2,369 2014 411 — 411 409 446 445 444 436 431 428 398 383 390 2015 1,782 — 1,782 1,690 1,384 1,339 1,258 1,228 1,207 1,185 1,172 1,156 2016 1,495 — 1,495 1,486 1,523 1,482 1,466 1,430 1,422 1,400 1,378 2017 1,719 — 1,719 1,605 1,518 1,518 1,479 1,445 1,415 1,452 2018 2,921 — 2,921 2,871 2,762 2,693 2,655 2,636 2,611 2019 2,340 — 2,340 2,307 2,177 2,085 2,031 2,070 2020(2) 2,205 (782) 1,423 1,494 1,521 1,641 1,662 2021(3) 3,709 1,611 5,320 5,178 4,822 4,612 2022(2) 2,649 782 3,431 3,360 3,282 2023 2,215 — 2,215 2,248 Adjusted Ultimate Losses* as a Percentage of Adjusted Assumed and Acquired Net Loss Reserves* At End of Year of Acquisition Years thereafter: Acquisition Year One Two Three Four Five Six Seven Eight Nine Ten (Unaudited) 2013 and prior 100 % 92 % 84 % 79 % 76 % 73 % 70 % 69 % 67 % 67 % 66 % 2014 100 % 109 % 108 % 108 % 106 % 105 % 104 % 97 % 93 % 95 % 2015 95 % 78 % 75 % 71 % 69 % 68 % 66 % 66 % 65 % 2016 99 % 102 % 99 % 98 % 96 % 95 % 94 % 92 % 2017 93 % 88 % 88 % 86 % 84 % 82 % 84 % 2018 98 % 95 % 92 % 91 % 90 % 89 % 2019 99 % 93 % 89 % 87 % 88 % 2020 105 % 107 % 115 % 117 % 2021 97 % 91 % 87 % 2022 98 % 96 % 2023 101 % (1) For the 2013 and prior acquisition year, the adjusted net reserves shown are as at December 31, 2013 and are not the adjusted net reserves assumed and acquired. (2) $782 million of Assumed and Acquired net losses and LAE relating to the Aspen ADC have been transferred from the 2020 to the 2022 acquisition year. Any PPD on this portfolio that occurred in the years ended December 31 2021 and 2020 has not been reclassified between periods. (3) 2021 Adjusted Assumed and Acquired net losses and LAE - Related Party of $1,611 million relates to the acquisition of Enhanzed Re and the transfer of StarStone International into the Run-Off segment. * Non-GAAP financial measure. Adjusted ultimate losses presented in the table represent the cumulative impact on adjusted acquired & assumed net loss reserves of adjusted PPD. Reconciliations of adjusted acquired and assumed net loss reserves and adjusted PPD are included on pages 27 to 29 in the Non-GAAP measures section.

| enstargroup.com 16 Capital Position & Credit Ratings Credit ratings (1) Standard and Poor’s Fitch Ratings Long-term issuer BBB+ (Outlook: Stable) BBB+ (Outlook: Stable) 2029 Senior Notes BBB+ BBB 2031 Senior Notes BBB BBB 2040 and 2042 Junior Subordinated Notes BBB- BBB- Series D and E Preferred Shares BBB- 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. Total Capitalization Attributable to Enstar $7,366 $6,803 $5,025 $4,464 $510 $510 $1,831 $1,829 24.9% 26.9% 31.8% 34.4% Debt and Series D and E Preferred Shares to total capitalization attributable to Enstar Debt to total capitalization attributable to Enstar Debt obligations Series D and E Preferred Shares Ordinary shareholders' equity December 31, 2023 December 31, 2022 Total Capitalization $7,479 $7,157 $5,025 $4,464 $510 $510 $113 $354 $1,831 $1,829 24.5% 25.6% 31.3% 32.7% Debt and Series D and E Preferred Shares to total capitalization Debt to total capitalization Debt obligations NCI and RNCI Series D and E Preferred Shares Ordinary shareholders' equity December 31, 2023 December 31, 2022

17 Non-GAAP Measures Non-GAAP Measure Definition Purpose of Non-GAAP Measure over GAAP Measure Fully diluted 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 the exercise of equity awards granted but not yet vested as, over the long term, this presents both management and investors with a more economically accurate measure of the realizable value of shareholder returns by factoring in the impact of share dilution. 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 consistent measure of the performance of our business by enabling comparison between the financial periods presented. We eliminate the impact of net realized and unrealized (gains) losses on fixed maturities and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as: • we typically hold most of our fixed maturities until the earlier of maturity or the time that they are used to fund any settlement of related liabilities which are generally recorded at cost; and • removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option. Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods. We include fair value adjustments as non-GAAP adjustments to the adjusted operating income (loss) attributable to Enstar ordinary shareholders as they are non-cash charges that are not reflective of the impact of our claims management strategies on our loss portfolios. We eliminate the net gain (loss) on the purchase and sales of subsidiaries and net earnings from discontinued operations, as these items are not indicative of our ongoing operations. We use this non-GAAP measure in our incentive compensation program. 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 maturities 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, and -adjustments attributable to noncontrolling interests Adjusted opening Enstar ordinary shareholders' equity (denominator) Opening Enstar ordinary shareholders' equity, less: -net unrealized gains (losses) on fixed maturities 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. We adjust our investment returns to eliminate the impact of the change in fair value of fixed maturities (both credit spreads and interest rates), as we typically hold most of these investments 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 maturities and funds held-directly managed; and -unrealized (gains) losses on fixed maturities, AFS included within OCI, net of reclassification adjustments and excluding foreign exchange. Adjusted average aggregate total investable assets (denominator) Total average investable assets, adjusted for: -net unrealized (gains) losses on fixed maturities, AFS included within AOCI -net unrealized (gains) losses on fixed maturities, trading (1) Comprises the discount rate and risk margin components.

| enstargroup.com 18 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 and comparable measurement of the impact of our claims management strategies on our loss portfolios across acquisition years and also to our overall financial periods. We use this measure to evaluate the impact of our claims management strategies because it provides visibility into our ability to settle our claims obligations for amounts less than our initial estimate at the point of acquiring the obligations. The following components of periodic recurring net incurred losses and LAE and net loss reserves are not considered key components of our claims management performance for the following reasons: • Prior to the settlement of the contractual arrangements, the results of our Legacy Underwriting segment were economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement(2); as such, the results were not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies; • The results of our Assumed Life segment relate only to our prior exposure to active property catastrophe business; as this business was not in run-off, the results were not a relevant contribution to Adjusted RLE; • The change in fair value of insurance contracts for which we have elected the fair value option(1) has been removed to support comparability between the two acquisition years for which we elected the fair value option in reserves assumed and the acquisition years for which we did not make this election (specifically, this election was only made in the 2017 and 2018 acquisition years and the election of such option is irrevocable); and • The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis. We include our performance in managing claims and estimated future expenses on our defendant A&E liabilities because such performance is relevant to assessing our claims management strategies even though such liabilities are not included within the loss reserves. 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 Assumed Life operations -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 net ultimate liabilities and reduction in estimated future expenses of our defendant A&E liabilities. Adjusted net loss reserves (denominator) Net losses and LAE, adjusted to: Remove: -Legacy Underwriting and Assumed Life net loss reserves -current period net loss reserves -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 A&E liability exposures and estimated future expenses. (1) Comprises the discount rate and risk margin components. (2) The reinsurance contractual arrangements (including the Capacity Lease Agreement) were settled during the second quarter of 2023. As a result of the settlement, we have not recorded any transactions in the Legacy Underwriting segment in 2023.

| enstargroup.com 19 Reconciliation to Fully Diluted Book Value Per Share For the Year Ended December 31, 2023 2022 2021 Equity (1) Ordinary Shares Per Share Amount Equity (1) (2) Ordinary Shares Per Share Amount Equity (1) Ordinary Shares Per Share Amount (in millions of U.S. dollars, except share and per share data) Book value per ordinary share $ 5,025 14,631,055 $ 343.45 $ 4,464 17,022,420 $ 262.24 $ 5,813 17,657,944 $ 329.20 Non-GAAP adjustment: Share-based compensation plans — 292,190 — 218,171 — 315,205 Fully diluted book value per ordinary share* $ 5,025 14,923,245 $ 336.72 $ 4,464 17,240,591 $ 258.92 $ 5,813 17,973,149 $ 323.43 For the Year Ended December 31, 2020 2019 Equity (1) Ordinary Shares Per Share Amount Equity (1) Ordinary Shares Per Share Amount (in millions of U.S. dollars, except share and per share data) Book value per ordinary share $ 6,326 21,519,602 $ 293.97 $ 4,490 21,511,505 $ 208.73 Non-GAAP adjustments: Share-based compensation plans — 298,095 — 302,565 Warrants 20 175,901 20 175,901 Fully diluted book value per ordinary share* $ 6,346 21,993,598 $ 288.56 $ 4,510 21,989,971 $ 205.11 (1) Equity comprises Enstar ordinary shareholders' equity, which is calculated as Enstar shareholders' equity less preferred shares ($510 million as of December 31, 2023, 2022, 2021, 2020 and 2019, respectively), prior to any non-GAAP adjustments. (2) Enstar ordinary shareholders’ equity as of December 31, 2022 has been retrospectively adjusted by $273 million for the impact of adopting ASU 2018-12. * Non-GAAP financial measure.

| enstargroup.com 20 Reconciliation to Adjusted Return on Equity - QTD Q4 2023 and 2022 (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. (1) Net income (loss) comprises net income (loss) 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) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations. (3) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance. (4) Comprises the discount rate and risk margin components. (5) 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. (6) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interests associated with the specific subsidiaries to which the adjustments relate. (7) Enstar ordinary shareholders’ equity as of September 30, 2022 has been retrospectively adjusted by $236 million for the impact of adopting ASU 2018-12. * Non-GAAP financial measure. Three Months Ended December 31, 2023 December 31, 2022 Net income (loss) (1) Opening equity (1) (Adj) ROE Net income (loss) (1) Opening equity (1)(7) (Adj) ROE Net income/Opening equity/ROE(1) $ 599 $ 4,367 13.7 % $ 227 $ 4,099 5.5 % Non-GAAP adjustments for loss (gains): Net realized losses on fixed maturities, AFS (2) / Net unrealized losses on fixed maturities, AFS (3) 10 634 23 757 Net unrealized losses on fixed maturities, trading (2) / Net unrealized losses on fixed maturities, trading (3) (108) 366 (53) 530 Net unrealized losses on funds held - directly managed (2) / Net unrealized losses on funds held - directly managed (3) (96) 222 50 639 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 (4) 54 (292) 28 (305) Amortization of fair value adjustments / Fair value adjustments 4 (112) (29) (95) Tax effects of adjustments (5) 5 — (1) — Adjustments attributable to noncontrolling interests (6) — — (21) — Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE* $ 468 $ 5,185 9.0 % $ 224 $ 5,625 4.0 %

| enstargroup.com 21 Reconciliation to Adjusted Return on Equity - 2023, 2022 and 2021 1) Net income (loss) comprises net income (loss) 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) Enstar ordinary shareholders’ equity as of December 31, 2022 has been retrospectively adjusted by $273 million for the impact of adopting ASU 2018-12. (3) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations. (4) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance. (5) Comprises the discount rate and risk margin components. (6) 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. (7) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interests associated with the specific subsidiaries to which the adjustments relate. *Non-GAAP measure. Year Ended December 31, 2023 December 31, 2022 December 31, 2021 Net income (loss) (1) Opening equity (1)(2) (Adj) ROE Net income (loss) (1) Opening equity (1) (Adj) ROE Net earnings (loss) (1) Opening equity (1) (Adj) ROE Net income (loss)/Opening equity/ROE (1) $ 1,082 $ 4,464 24.2 % $ (906) $ 5,813 (15.6) % $ 502 $ 6,326 7.9 % Non-GAAP adjustments for loss (gains): Net realized losses on fixed maturities, AFS (3) / Net unrealized losses on fixed maturities, AFS (4) 65 647 111 36 4 (82) Net unrealized losses on fixed maturities, trading (3) / Net unrealized losses on fixed maturities, trading (4) (84) 400 503 (134) 144 (384) Net unrealized losses on funds held - directly managed (3) / Net unrealized losses on funds held - directly managed (4) (47) 780 567 9 62 (94) 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 (5) 78 (294) (200) (107) (75) (33) Amortization of fair value adjustments / Fair value adjustments 17 (124) (18) (106) 16 (128) Net gain on purchase and sales of subsidiaries — — — — (73) — Tax effects of adjustments (6) (7) — (7) — (21) — Adjustments attributable to noncontrolling interests (7) (2) — (111) — 6 — Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE* $ 1,102 $ 5,873 18.8 % $ (61) $ 5,511 (1.1) % $ 565 $ 5,605 10.1 %

| enstargroup.com 22 Reconciliation to Adjusted Return on Equity - 2020 and 2019 Year Ended December 31, 2020 December 31, 2019 Net income (loss) (1) Opening Equity (1) (Adj) ROE Net income (loss) (1) Opening Equity (1) (7) (Adj) ROE (in millions of U.S. dollars) Net income (loss)/Opening equity/ROE (1) $ 1,723 $ 4,490 38.4 % $ 906 $ 3,546 25.5 % Non-GAAP adjustments for loss (gains): Net realized losses (gains) on fixed maturities, AFS (2) / Net unrealized losses (gains) on fixed maturities, AFS (3) (18) — (4) (1) Net unrealized (gains) losses on fixed maturities, trading (2) / Net unrealized losses (gains) on fixed maturities, trading (3) (228) (229) (423) 187 Net unrealized (gains) losses on funds held - directly managed (2) / Net unrealized losses (gains) on funds held - directly managed (3) (60) (48) (89) 41 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 (4) 119 (130) 117 (244) Amortization of fair value adjustments / Fair value adjustments 27 (152) 51 (199) Net gain on purchase and sales of subsidiaries (3) — — — Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations (16) (266) (7) (210) Tax effects of adjustments (5) 23 — 36 — Adjustments attributable to noncontrolling interests (6) 13 109 15 86 Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE* $ 1,580 $ 3,774 41.9 % $ 602 $ 3,206 18.8 % (1) Net income (loss) comprises net income (loss) 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) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations. (3) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance. (4) Comprises the discount rate and risk margin components. (5) 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. (6) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interest associated with the specific subsidiaries to which the adjustments relate. (7) The 2018 balance sheet has not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. * Non-GAAP financial measure.

| enstargroup.com 23 Reconciliation to Adjusted Run-off Liability Earnings - 2023 and 2022 Year Ended As of Year Ended December 31, 2022 December 31, 2022 December 31, 2021 December 31, 2022 December 31, 2022 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % PPD/net loss reserves/RLE % $ 756 $ 12,011 $ 11,926 $ 11,969 6.3 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (45) — (23) Assumed Life (55) — (181) (91) Legacy Underwriting 3 (135) (153) (144) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies (18) 124 106 115 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) (200) 294 107 201 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 2 572 573 573 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 1 35 37 37 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 489 $ 12,856 $ 12,415 $ 12,637 3.9 % (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure. Year Ended As of Year Ended December 31, 2023 December 31, 2023 December 31, 2022 December 31, 2023 December 31, 2023 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % PPD/net loss reserves/RLE % $ 131 $ 11,585 $ 12,011 $ 11,798 1.1 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (30) — (15) Legacy Underwriting — — (139) (69) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 17 107 124 116 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 78 246 294 270 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities (1) 527 572 550 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 2 33 35 34 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 227 $ 12,468 $ 12,897 $ 12,684 1.8 %

| enstargroup.com 24 Reconciliation to Adjusted Run-off Liability Earnings - 2021 and 2020 Year Ended As of Year Ended December 31, 2021 December 31, 2021 December 31, 2020 December 31, 2021 December 31, 2021 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 403 $ 11,926 $ 8,763 $ 10,344 3.9 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (143) — (72) Assumed Life — (179) — (90) Legacy Underwriting (6) (140) (955) (548) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 16 106 128 117 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) (75) 107 33 70 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 38 573 615 594 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 5 37 43 40 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 381 $ 12,287 $ 8,627 $ 10,455 3.6 % Year Ended As of Year Ended December 31, 2020 December 31, 2020 December 31, 2019 December 31, 2020 December 31, 2020 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 32 $ 8,763 $ 7,941 $ 8,352 0.4 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (273) — (137) Legacy Underwriting (4) (702) (1,184) (943) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 28 128 152 140 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 119 33 130 82 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 103 615 561 588 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 9 43 52 48 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 287 $ 8,607 $ 7,652 $ 8,129 3.5 % (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure.

| enstargroup.com 25 Reconciliation to Adjusted Run-off Liability Earnings - 2019 Year Ended As of Year Ended December 31, 2019 December 31, 2019 December 31, 2018 December 31, 2019 December 31, 2019 RLE / PPD Net loss reserves Net loss reserves (2) Average net loss reserves (2) RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 4 $ 7,941 $ 7,341 $ 7,641 0.1 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (401) — (201) Legacy Underwriting 106 (842) (1,162) (1,002) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 51 152 199 176 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 117 130 244 187 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 4 561 84 323 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 3 52 20 36 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 285 $ 7,593 $ 6,726 $ 7,160 4.0 % (1) Comprises the discount rate and risk margin components. (2) The 2018 balance sheet has not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. * Non-GAAP financial measure.

| enstargroup.com 26 Reconciliation to Adjusted Total Investment Return Three Months Ended December 31, Year Ended December 31, 2023 2022 2023 2022 2021 2020 2019 Net investment income $ 176 $ 153 $ 647 $ 455 $ 312 $ 303 $ 308 Net realized (losses) gains (10) (23) (65) (111) (61) 19 5 Net unrealized gains (losses) 306 38 528 (1,503) 178 1,623 1,007 (Losses) income from equity method investments (9) (86) 13 (74) 93 239 56 Other comprehensive income: Unrealized gains (losses) on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange 220 87 222 (570) (100) 70 (3) TIR ($) $ 683 $ 169 $ 1,345 $ (1,803) $ 422 $ 2,254 $ 1,373 Non-GAAP adjustments: Net unrealized (gains) losses on fixed maturities, trading and funds held-directly managed (194) 20 (66) 1,181 210 (306) (516) Unrealized (gains) losses on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange (220) (87) (222) 570 100 (70) 3 Adjusted TIR ($)* $ 269 $ 102 $ 1,057 $ (52) $ 732 $ 1,878 $ 860 Total investments 17,413 18,210 17,413 18,210 19,616 15,893 13,096 Cash and cash equivalents, including restricted cash and cash equivalents 830 1,330 830 1,330 2,092 1,373 971 Total investable assets $ 18,243 $ 19,540 $ 18,243 $ 19,540 $ 21,708 $ 17,266 $ 14,067 Average aggregate invested assets, at fair value (1) $ 18,472 $ 19,503 $ 18,607 $ 20,079 $ 20,840 $ 15,443 $ 13,758 Annualized TIR % (2) 14.8 % 3.5 % 7.2 % (9.0) % 2.0 % 14.6 % 10.0 % Non-GAAP adjustment: Net unrealized losses (gains) on fixed maturities, AFS included within AOCI and net unrealized losses on fixed maturities, trading and funds held - directly managed 725 1,827 725 1,827 (89) (560) (275) Adjusted investable assets* $ 18,968 $ 21,367 $ 18,968 $ 21,367 $ 21,619 $ 16,706 $ 13,792 Adjusted average aggregate invested assets, at fair value* (3) $ 19,445 $ 21,380 $ 19,769 $ 21,165 $ 20,561 $ 15,153 $ 13,646 Annualized adjusted TIR %* (4) 5.5 % 1.9 % 5.3 % (0.2) % 3.6 % 12.4 % 6.3 % (1) This amount is a two period average of the total investable assets for the three months ended December 31, 2023 and 2022, respectively, and a five period average for the years ended December 31, 2023, 2022, 2021, 2020 and 2019, 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 ($) by average aggregate invested assets, at fair value. (3) This amount is a two period average of the adjusted investable assets* for the three months ended December 31, 2023 and 2022, respectively, and a five period average for the years ended December 31, 2023, 2022, 2021, 2020 and 2019, respectively, as presented above. (4) Annualized adjusted TIR %* is calculated by dividing the annualized adjusted TIR* ($) by adjusted average aggregate invested assets, at fair value*. *Non-GAAP measure.

| enstargroup.com 27 Reconciliation of PPD by Acquisition Year PPD in year ended December 31, Acquisition year 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) 2013 and prior PPD 289 282 160 133 107 86 60 43 14 11 Legacy (19) (22) (13) (21) (14) (8) (7) (6) 3 — FVA 21 15 24 14 15 14 7 5 12 2 2013 and prior Adjusted PPD* 291 275 171 126 108 92 60 42 29 13 2014 PPD 30 18 18 34 (112) (110) 1 25 30 21 Legacy (11) (39) (14) (27) 127 115 3 8 (14) (26) FVA (17) (16) (3) (6) (7) — (1) (3) (1) (2) 2014 Adjusted PPD* 2 (37) 1 1 8 5 3 30 15 (7) 2015 PPD — 87 301 42 79 28 20 21 12 15 FVA — 5 5 3 2 2 1 1 1 1 2015 Adjusted PPD* — 92 306 45 81 30 21 22 13 16 2016 PPD — — 9 (34) 18 9 21 10 14 19 Defendant A&E — — — — 23 4 13 (4) 7 2 Defendant A&E ULAE — — — (3) — 3 2 2 1 1 2016 Adjusted PPD* — — 9 (37) 41 16 36 8 22 22 2017 PPD — — — 84 98 (84) (50) 89 183 (89) FVO — — — 30 (11) 84 89 (55) (153) 52 2017 Adjusted PPD* — — — 114 87 — 39 34 30 (37) 2018 PPD — — — — 33 42 18 45 58 (12) Legacy — — — — 2 (1) — — — — FVO — — — — 18 33 30 (20) (47) 26 FVA — — — — (3) 35 21 13 8 11 2018 Adjusted PPD* — — — — 50 109 69 38 19 25 2019 PPD — — — — — 33 33 47 59 (37) Defendant A&E — — — — — — 90 42 (5) (3) Defendant A&E ULAE — — — — — — 7 3 — 1 2019 Adjusted PPD* — — — — — 33 130 92 54 (39) 2020 PPD — — — — — — (71) (27) (120) (21) 2020 Adjusted PPD* — — — — — — (71) (27) (120) (21) * Non-GAAP financial measure. Cumulative Adjusted PPD on page 14 is merely the sum of the relevant numbers in the table above.

| enstargroup.com 28 Reconciliation of PPD by Acquisition Year (continued) * Non-GAAP financial measure. Cumulative Adjusted PPD on page 14 is merely the sum of the relevant numbers in the table above. PPD in year ended December 31 Acquisition year 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (in millions of U.S. dollars) 2021 PPD — — — — — — — 150 435 179 Legacy — — — — — — — (8) 14 26 Assumed Life — — — — — — — — (55) — FVA — — — — — — — — (38) 5 2021 Adjusted PPD* — — — — — — — 142 356 210 2022 PPD — — — — — — — — 71 78 2022 Adjusted PPD* — — — — — — — — 71 78 2023 PPD — — — — — — — — — (33) 2023 Adjusted PPD* — — — — — — — — — (33) All Acquisition Years PPD 319 387 488 259 223 4 32 403 756 131 Legacy (30) (61) (27) (48) 115 106 (4) (6) 3 — Assumed Life — — — — — — — — (55) — FVO — — — 30 7 117 119 (75) (200) 78 FVA 4 4 26 11 7 51 28 16 (18) 17 Defendant A&E — — — — 23 4 103 38 2 (1) Defendant A&E ULAE — — — (3) — 3 9 5 1 2 All Acquisition Years Adjusted PPD* 293 330 487 249 375 285 287 381 489 227

| enstargroup.com 29 Reconciliation of Assumed and Acquired Reserves Non-GAAP Adjustments (2): Adjusted Assumed and Acquired net losses and LAE* Acquisition year Assumed and Acquired net losses and LAE Enhanzed Re Legacy Underwriting Fair value adjustments - acquired companies Fair value adjustments - fair value option Net Defendant A&E Liabilities Transfer from Legacy Underwriting (3) Adjusted Assumed and Acquired net losses and LAE* Third Party Related Party Total* 2013 and prior reserves as at Dec 31 2013 (1) $ 3,592 $ — $ (200) $ 184 $ — $ — $ — $ 3,576 $ 3,576 $ — $ 3,576 2014 1,057 — (592) (54) — — — 411 411 — 411 2015 1,756 — — 26 — — — 1,782 1,782 — 1,782 2016 1,357 — — — — 138 — 1,495 1,495 — 1,495 2017 1,536 — (32) 1 214 — — 1,719 1,719 — 1,719 2018 2,757 — (16) 102 78 — — 2,921 2,921 — 2,921 2019 1,817 — — — — 523 — 2,340 2,340 — 2,340 2020(4) 1,409 — — — 14 — — 1,423 1,423 — 1,423 2021 4,550 (221) — 36 — — 955 5,320 3,709 1,611 5,320 2022(4) 3,431 — — — — — — 3,431 3,431 — 3,431 2023 2,215 — — — — — — 2,215 2,215 — 2,215 (1) For the 2013 and prior acquisition years, the net reserves shown are as at December 31, 2013, and are not the net reserves assumed and acquired. (2) This reconciliation excludes any adjustment for current accident year loss reserves as it references only reserves assumed and acquired by Enstar. (3) Represents the transfer of StarStone International net losses and LAE from Legacy Underwriting to Run-off segment effective January 1, 2021. (4) $782 million of Assumed and Acquired net losses and LAE relating to the Aspen ADC have been transferred from the 2020 to the 2022 acquisition year. * Non-GAAP financial measure.

| enstargroup.com 30 Investment Composition - December 31, 2023 Other Investments Equities Cash (2) Funds Held Short-term and fixed maturities, trading and AFS December 31, 2023 Hedge Funds Fixed income funds Equity funds Private equity funds CLO equities CLO equity funds Private credit funds Real estate debt fund Other (1) Publicly traded equities Exchange- traded funds Privately held equities Short-term and fixed maturities, trading and AFS $ 7,274 39.9 % 7,274 Funds held 5,251 28.8 % 102 68 5,081 — % 1.9 % — % — % — % — % — % — % — % — % 1.3 % — % — % 96.8 % — % Equities Publicly traded equities 275 1.5 % 55 220 Exchange-traded funds 82 0.4 % 18 20 44 Privately held equities 344 1.9 % 45 299 Total 701 3.8 % — % 7.8 % — % — % 2.6 % — % 6.4 % — % — % 31.4 % 2.9 % 42.6 % — % — % 6.3 % Other investments Hedge funds 491 2.7 % 407 84 Fixed income funds 605 3.3 % 605 Equity funds 4 — % 4 Private equity funds 1,617 8.9 % 3 1,186 108 67 92 16 30 6 109 CLO equities 60 0.3 % 60 CLO equity funds 182 1.0 % 182 Private credit funds 625 3.4 % 625 Real estate debt fund 269 1.5 % 269 Total 3,853 21.1 % 10.5 % 18.0 % — % 30.8 % 6.3 % — % 19.0 % 8.7 % 2.4 % 0.5 % 0.8 % 0.2 % 2.8 % — % — % Equity method investments 334 1.8 % Total investments 17,413 95.5 % Cash and cash equivalents (including restricted cash) 830 4.6 % 830 Total investable assets $ 18,243 100.0 % (1) Infrastructure in fund format. (2) Cash and cash equivalents.

| enstargroup.com 31 Investment Composition - December 31, 2022 Other Investments Equities December 31, 2022 Hedge Funds Fixed income funds Equity funds Private equity funds CLO equities CLO equity funds Private credit funds Real estate debt fund Other(1) Publicly traded equities Exchange- traded funds Privately held equities Cash(2) Short-term and fixed maturity investments, trading and AFS $ 7,645 39.1 % Funds held 5,622 28.8 % Equities Publicly traded equities 385 2.0 % 385 Exchange-traded funds 507 2.6 % 68 439 Privately held equities 358 1.8 % 52 25 178 103 Total 1,250 6.4 % — % 9.6 % — % — % 2.0 % — % 14.2 % — % — % 30.8 % 35.1 % 8.2 % — % Other investments Hedge funds 549 2.8 % 468 81 Fixed income funds 547 2.8 % 547 Equity funds 3 — % 3 Private equity funds 1,282 6.6 % 159 825 96 59 28 13 58 6 38 CLO equities 148 0.8 % 148 CLO equity funds 203 1.0 % 203 Private credit funds 362 1.9 % 362 Real estate debt fund 202 1.0 % 202 Total 3,296 16.9 % 14.2 % 23.9 % — % 25.0 % 10.6 % — % 13.9 % 7.9 % 0.8 % 0.5 % 1.8 % 0.2 % 1.2 % Equity method investments 397 2.0 % Total investments 18,210 93.2 % Cash and cash equivalents (including restricted cash) 1,330 6.8 % 1,330 Total investable assets $ 19,540 100.0 % (1) Infrastructure in fund format. (2) Cash and cash equivalents.

enstargroup.com Q4 2023 Year-End Review February 2024 Enstar Group Overview

Property of Enstar Group – Not for Distribution 2 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, the performance of our investment portfolio and liquidity, and other factors detailed in Part I, Item 1A. Risk Factors in our Annual Report on Form 10-K for the year ended December 31, 2023 (which will be filed with the Securities and Exchange Commission ("SEC")), Part 1, Item 1A. Risk Factors in our Annual Report on Form 10-K for the year ended December 31, 2022 and our other reports filed from time to time with the 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. NON-GAAP FINANCIAL MEASURES In addition to our key financial measures presented in accordance with GAAP, this presentation includes 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 programs. These non-GAAP financial measures provide an additional view of our operational performance over the long-term and allow investors 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. Refer to slides 29 through 36 of this presentation for further details regarding our non-GAAP measures and reconciliations of these measures to the most directly comparable GAAP measure. 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. 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. DISCLAIMER

KEY MESSAGES

Property of Enstar Group – Not for Distribution 4 $20.9bn $12.9bn $5.5bn Total Assets Total Gross Reserves1 Shareholders’ Equity Enstar is the largest standalone provider with a 30-year record of successfully acquiring and managing run-off while creating shareholder value Deals Completed Since Inception 117 1. Includes losses and loss adjustment expenses and defendant A&E liabilities. DOMINANT GLOBAL PROVIDER OF INNOVATIVE LEGACY SOLUTIONS

Property of Enstar Group – Not for Distribution 5 Leading suite of innovative risk transfer solutions in a large and growing legacy market Dominant Legacy Provider Unparalleled Competitive Advantages Best positioned to execute on both large and bespoke value additive transactions due to size, scale and experience Best-in-class Claims Management “Enstar Effect” drives Run-off Liability Earnings (“RLE”) industry outperformance Highly Disciplined Approach Consistent financial and operational discipline applied to portfolio acquisitions to drive value Balance Sheet Strength Strong balance sheet ensures ample capital availability, no near- term debt maturities Successful execution of our strategy positions us well for long-term growth in book value and return on equity GENERATING SHAREHOLDER VALUE Durable business model designed to succeed across multiple insurance cycles

Property of Enstar Group – Not for Distribution 6 ANOTHER YEAR OF STRATEGIC DELIVERY Year ended December 31, 2023 $1.1bn Net Income 24.2% Return on Equity 31.0% Growth in Book Value Per Share STRONG FY23 PERFORMANCE RATINGS Received upgrade from S&P to BBB+ on long- term issuer credit rating SHARE REPURCHASE Purchased a total of $532 million LIQUIDITY AND SOLVENCY Excess capital and liquidity available to deploy to value accretive M&A Upsized revolving credit agreement to $800 million M&A Completed loss portfolio transfers with QBE, RACQ and a bespoke transaction with AIG, assuming total net loss reserves of $2.2 billion

Property of Enstar Group – Not for Distribution 7 30+ year history operating in run-off space 117 total acquisitive transactions completed to date 15 18 27 32 38 46 59 73 85 94 106 120 131 153 170 165 209 294 329 262 343 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 CREATING SHAREHOLDER VALUE SINCE INCEPTION Book value per common share in USD

Property of Enstar Group – Not for Distribution 8 WELL-POSITIONED FOR LONG-TERM VALUE CREATION Current Book Value $343/per share as of December 31, 2023 Economic Value Fixed Income Pull to Par and GAAP Accounting Impacts Franchise Value M&A Pipeline and best-in-class Claims Management Building blocks to total value

Property of Enstar Group – Not for Distribution 9 MANAGEMENT WELL-ALIGNED WITH SHAREHOLDERS Seasoned leadership with exceptional track record of value creation Orla Gregory President Years at Enstar: 20 Industry Experience: 30+ years Age: 49 David Ni Chief Strategy Officer Years at Enstar: 4 Industry Experience: 18+ years Age: 40 Dominic Silvester CEO & Co-founder Years at Enstar: 30 Industry Experience: 41+ years Age: 63 Paul Brockman Chief Operations Officer & Chief Claims Officer Years at Enstar: 11 Industry Experience: 32+ years Age: 51 Nazar Alobaidat Chief Investment Officer Years at Enstar: 7 Industry Experience: 22+ years Age: 46 Matthew Kirk Chief Financial Officer Years at Enstar: 3 Industry Experience: 28+ years Age: 50 Seema Thaper Group Chief Risk Officer Years at Enstar: 4 Industry Experience: 21+ years Age: 43 Laurence Plumb Chief of Business Operations Years at Enstar: 3 Industry Experience: 17+ years Age: 40 Audrey Taranto General Counsel Years at Enstar: 11 Industry Experience: 12+ years Age: 44 ~22%* Management and Board Representation Ownership 25 years Average Industry Experience * Includes directors, officers and significant shareholders who are affiliated with directors (including funds managed by Stone Point Capital LLC and its affiliates, and Beck Mack & Oliver). Percentages are calculated using 15,196,685 voting ordinary shares outstanding as of December 31, 2023 (including 565,630 voting ordinary shares underlying awards issued pursuant to Enstar's Joint Share Ownership Program) and excluding unvested equity awards held by directors and officers. With respect to shareholders, percentages are calculated using the most recent publicly available information.

Property of Enstar Group – Not for Distribution 10 3 2 KEY MESSAGES 1Strong competitive advantage ideally places us to create significant value for shareholders in the years ahead. Dominant innovative legacy solutions provider and largest run- off dedicated firm Time-tested business model positions us as the clear market leader in a large and growing sector Delivering exceptional value to shareholders with an aligned management team

BUSINESS AND MARKET

Property of Enstar Group – Not for Distribution 12 Deliver Innovative Legacy and Risk Management Solutions to Insurance Market Industry founder and largest standalone provider Generate Positive Claims Outcomes Best-in-class claims function or "Enstar Effect” drives decades of Run-off Liability Earnings Growing Asset Base Using Origination Capabilities $18.2bn investable assets; 4.2x investment leverage1 How We Do It Specialized M&A Expertise Well Established Leadership, Culture and Capabilities Investments and Capital Optimization Best-in-class Claims Function 1. Investment leverage is calculated as average investable assets for the year ended December 31, 2023, divided by opening equity as of December 31, 2022. FULL SUITE OF MARKET-LEADING RISK MANAGEMENT SOLUTIONS DESIGNED TO CREATE SHAREHOLDER VALUE What We Do

Property of Enstar Group – Not for Distribution 13 Prudent Return of Capital to Shareholders Excess capital not required for M&A pipeline returned to shareholders Enstar Run-off Business Model Leverage our industry relationships and position to source new business opportunities Fully-integrated M&A and Claims units provide ground-up view of risk Source, Diligence and Acquire New Portfolios Redeploy Capital Apply claims management strategies to generate Run-off Liability Earnings and manage investments to obtain attractive risk adjusted returns Manage Liabilities and Investments Reduce capital requirements as claims are settled; any excess may be redeployed in the business CONSISTENT ECONOMIC MODEL Strong source of book value growth and internal financing

Property of Enstar Group – Not for Distribution 14 1. TIR and RLE leverage factors are calculated as average investable assets and average net loss reserves, respectively, for the year ended December 31, 2023, divided by opening equity as of December 31, 2022. 2. Non-cash items include amortization of net deferred charge assets. TOTAL INVESTMENT RETURN (“TIR”) Leverage Factor1: 4.2x RUN-OFF LIABILITY EARNINGS (“RLE”) Leverage Factor1: 2.6x EXPENSES & OTHER (INC. NON-CASH2) Return On Equity RETURN ON EQUITY (“ROE”) COMPONENTS Generating attractive returns

Property of Enstar Group – Not for Distribution 15 Same return across all 3 transaction types TIR Leverage factor1: 4.2x RLE Leverage factor1: 2.6x 1. TIR and RLE leverage factors are calculated as average investable assets and average net loss reserves, respectively, for the year ended December 31, 2023, divided by opening equity as of December 31, 2022 Transaction 1 (RLE Focused) Transaction 2 (Combination) Transaction 3 (TIR Focused) TIR Hypothetical Deal Returns Historical deals with claims control generate RLE via “Enstar Effect” Offer clients bespoke solutions which result in TIR returns to Enstar Similar returns regardless of deal type TIR TIR RLE RLE RLE PROFITABILITY VIEW BY DEAL TYPE Well-positioned to deliver sustainable returns from evolving legacy solutions market Enstar’s innovative legacy solutions ensure flexible profitability profile to generate attractive returns

Property of Enstar Group – Not for Distribution 16 Balance Sheet and Capital Relief Key Market Drivers Source: PwC Global Insurance Run-off Survey 2022. North America $464bn UK & Continental Europe $319bn Rest of World $177bn SIGNIFICANT GROWING RUN-OFF MARKET $960bn opportunity, propelled by favourable global tailwinds Eliminate Administration and Management Burden from Non-Core Lines Facilitate M&A or IPO Transactions Improve Equity Story / Facilitate Re-Rating of Business Resolve Concentration Risk Remove Balance Sheet Uncertainty Divest Business Line or Non-Core Operations Release Trapped Capital Facilitate Growth Risk Management Capital Management Strategic Activity

Property of Enstar Group – Not for Distribution 17 Data from January 2020 – January 2024 1. Excludes Enhanzed Re and transaction with AIG. 261 opportunities reviewed ~$85.7bn of net reserves 17 1 deals completed $10.3bn1 of reserves Executing on opportunities that meet our risk parameters and profitability hurdles ROBUST TRANSACTION PIPELINE Consistent financial and operational discipline applied to pipeline to drive returns

Property of Enstar Group – Not for Distribution 18 `` Run-off Focused Diversified Business Riverstone Int. DARAG Marco Compre Swiss Re NICO Longevity (>20yrs in Operation) Presence in Global Run- off Markets Experience in All Types of Run-off Transactions Transaction above $1.5bn acquired reserves Not Published Deals Announced Since Inception1 117 ~37 ~67 ~8 ~40-50 N.A. N.A. Shareholders’ Equity ($ Billions)2 5.5 ~1.2 2 Not Published ~0.2 2 ~0.7 2 ~12.7 2 ~200 2, 3 1 These approximations are based upon publicly announced transactions as per the respective company’s website. 2 As of latest company filings. As of 31-Dec- 2023 for Enstar. As of 30-Sep-2023 for Riverstone, Swiss Re and NICO. As of 30- Jun-2023 for Compre. As of 31-Dec-2022 for Marco. 3 Reflects policy-holders’ surplus. COMPETITIVE LANDSCAPE Unparalleled leadership in global run-off market, built on scale, flexibility, and track record of claims management excellence

PERFORMANCE

Property of Enstar Group – Not for Distribution 20 *Non-GAAP financial measure. Refer to "Non-GAAP Financial Measures" in the Appendix for explanatory notes and a reconciliation to the most directly comparable GAAP measure. 24.2% 18.8% Adjusted ROE* 7.2% 5.3% Adjusted TIR* 31.0% $532m Capital Returned to Common Shareholders ROE TIR $2.2bn Net Loss Reserves Assumed 1.1% 1.8% Adjusted RLE* RLE Book Value Growth FINANCIAL HIGHLIGHTS Full Year 2023

Property of Enstar Group – Not for Distribution 21 5-YEAR ROE AND ADJUSTED ROE* * Non-GAAP measure; refer to slides 29 to 36 for reconciliation to the applicable GAAP financial measure. ** Adjusted ROE is a Non-GAAP measure. Due to trading accounting elections on certain of our investment assets, ROE calculated in accordance with GAAP includes the impact of net realized and unrealized gains (losses) on fixed maturity and funds held-directly managed, which can be material. Consequently, ROE calculated in accordance with GAAP is interest rate sensitive and will have greater variability than our Adjusted ROE. As such, reconciliation of ROE to Adjusted ROE calculated in accordance with GAAP is not accessible on a forward-looking basis because we believe that it is not possible without unreasonable effort to provide with reasonable accuracy an expected range for the impact of net realized and unrealized gains (losses) on fixed maturity investments and funds held-directly managed. However, given that unrealized fixed income losses reduced our GAAP equity base in 2022, we expect our annual average ROE calculated in accordance with GAAP will be higher than our annual average Adjusted ROE until our unrealized fixed income losses recover, subject to the potential impact of future net realized and unrealized losses. 25.5% 38.4% 7.9% -15.6% 24.2% 16.1% 18.8% 41.9% 10.1% -1.1% 18.8% 17.7% 2019 2020 2021 2022 2023 Average 2019 - 2023 Return on Equity and Adjusted Return on Equity* Return on Equity Adjusted Return on Equity* Targeting long- term Adjusted ROE low to mid-teens**

Property of Enstar Group – Not for Distribution 22 $14.1 $17.3 $21.7 $19.5 $18.2 2019 2020 2021 2022 2023 $7.9 $8.8 $11.9 $12.0 $11.6 2019 2020 2021 2022 2023 Investable Assets1 ($bn) Net Loss Reserves ($bn) 1. Investable assets is the sum of total investments, cash and cash equivalents and restricted cash and cash equivalents. CAGR 5.3% STRONG BALANCE SHEET GROWTH WITH PRUDENT CAPITAL MANAGEMENT A platform for delivering balanced and sustainable growth through investable assets and reserves CAGR 7.8% $0.0 $26.0 $942.0 $163.0 $532.0 2019 2020 2021 2022 2023 Capital Returns ($m)

Property of Enstar Group – Not for Distribution 23 THE ENSTAR EFFECT CLAIMS CONTROL (Directly Managed) EARLY TRIAGE OF CLAIMS PORTFOLIO • Detailed on a claim-by-claim basis BESPOKE SETTLEMENT STRATEGY FOR EVERY CLAIM • Data-driven approach provides comprehensive top-down, bottom-up view WORK CLAIMS FASTER • Reach equitable settlements quickly to mitigate exposures and reduce claims handling expense • Proven and successful claims execution drives P&C industry outperformance 02 04 CLAIMS OVERSIGHT (Indirectly Managed) 02 SIGNIFICANT IN NON- TRADITIONAL SOLUTIONS • Attractive partnership feature 03 COMPLEMENTARY CLAIMS MONITORING • Via management & claims committees 04 ALIGNMENT THROUGH CLAIMS RECOMMENDATION RIGHTS • When certain financial thresholds are met 01 DUE DILIGENCE • Claims unit integrated in M&A and Pricing process • In-house independent view of claims and reserve adequacy 03 THE ENSTAR EFFECT For most insurance companies, claims experience is an expense item For Enstar, driving superior claims outcomes is a major competitive advantage

Property of Enstar Group – Not for Distribution 24 Enstar Loss Reserve Outperformance vs US P&C Industry1,2 Five Years Ended 2022 Enstar delivered better net loss reserve outcomes 2.9% 6.5% 8.6% General Casualty Workers' Compensation Asbestos & Environmental 1. We calculated the change in estimates of net ultimate losses for the five years ended December 31, 2022 divided by average net loss reserves on three of our largest lines of business within our Run-off segment (General Casualty, Workers’ Compensation and Asbestos & Environmental) as well as in aggregate for the Run-off segment and compared the results to the total of the Combined US P&C Industry (source: US Annual Statements through SNL). To remove any potential distortions due to mix of accident years, we have matched the industry reserves’ accident-year-weighting to match Enstar’s. 2. The weighted average reduction in estimates of net ultimate losses divided by average net loss reserves by line of business relating to our Run-off segment for the five years ended December 31, 2022 was as follows: i) General Casualty – Enstar (1.2)%, Industry (4.1)%; ii) Workers’ Compensation – Enstar 11.0%, Industry 4.5%; iii) Asbestos & Environmental – Enstar 0.9%, Industry (7.7)%. ENSTAR EFFECT DRIVES OUTPERFORMANCE General Casualty $4.1 Workers' Compensation $1.7 Asbestos & Environmental $1.8 All Other $4.0 Enstar Total 4Q23 Net Loss Reserves ($ in billions)

APPENDIX enstargroup.com

Property of Enstar Group – Not for Distribution 26 INVESTMENT PORTFOLIO COMPOSITION $18.2bn Total Investable Assets1 $17.1bn Investment Portfolio 2 $0.8bn Cash and restricted cash 4.04 yrs Average Duration 3 3.86% Book Yield A+ Average Investment Portfolio Credit Rating 4 Funds Held5 Other InvestmentsFixed Maturities Equities Cash and Cash Equivalents 1. Investable assets is the sum of total investments, cash and cash equivalents and restricted cash and cash equivalents. 2. Excludes cash and cash equivalents, restricted cash and cash equivalents and equity method investments. 3. The average duration calculation includes cash and cash equivalents, short-term investments and fixed maturity securities, as well as the fixed maturity securities and cash and cash equivalents within our funds held – directly managed portfolios. 4. The average credit ratings calculation includes cash and cash equivalents, short-term investments, fixed maturity securities and the fixed maturity securities within our funds held – directly managed portfolios. 5. Includes funds held by reinsured companies and other assets within funds held – directly managed. Fixed Income, Trading and AFS U.S. government & agency 1.8 % U.K. government 0.4 % Other government 2.1 % Corporate 22.7 % Municipal 0.8 % Residential mortgage-backed 2.7 % Commercial mortgage-backed 4.6 % Asset-backed 4.8 % Total 39.9 % Other Investments Private equity funds 8.9 % Fixed income funds 3.3 % Private credit funds 3.4 % Hedge funds 2.7 % CLO equities 0.3 % CLO equity funds 1.0 % Real estate funds 1.5 % Total 21.1 % Equities Publicly traded equities 1.5 % Exchange-traded funds 0.4 % Privately held equities 1.9 % Total 3.8 % Equity Method Investments Investable Assets (as of December 31, 2023) Composition by Asset Class

Property of Enstar Group – Not for Distribution 27 FINANCIAL DATA Summary Income Statement $ millions Three Months Ended December 31, 2023 Three Months Ended December 31, 2022 Year Ended December 31, 2023 Year Ended December 31, 2022 Net premiums earned $ 14 $ 14 $ 43 $ 66 Net investment income and net realized and unrealized gains (losses) 472 168 1,110 (1,159) Other income (expense) (4) 2 276 35 Net incurred losses and LAE 84 271 101 708 Policyholder benefit expenses — — — (25) Amortization of net deferred charge assets (31) (20) (106) (80) Acquisition costs (4) (3) (10) (23) Interest expense (23) (18) (90) (89) General and administrative expenses and net foreign exchange losses (128) (109) (369) (316) Income tax benefit (expense) 238 18 250 12 (Losses) income from equity method investments (9) (86) 13 (74) Net income (loss) 609 235 1,218 (945) Net (income) loss attributable to noncontrolling interests (1) 1 (100) 75 Dividends on preferred shares (9) (9) (36) (36) Net income (loss) attributable to Enstar ordinary shareholders $ 599 $ 227 $ 1,082 $ (906)

Property of Enstar Group – Not for Distribution 28 FINANCIAL DATA Summary Balance Sheet $ millions December 31, 2023 December 31, 2022 Assets Investable assets 18,243 19,540 Reinsurance balances recoverable 957 1,131 Net deferred charge assets 731 658 Other 982 825 Total Assets 20,913 22,154 Liabilities Losses and loss adjustment expenses 12,359 13,007 Future policyholder benefits — 821 Defendant asbestos and environmental liabilities 567 607 Debt obligations 1,831 1,829 Other 508 562 Total Liabilities 15,265 16,826 Redeemable noncontrolling interests (“RNCI”) — 168 Shareholders' Equity Ordinary shareholders’ equity 5,025 4,464 Series D & E preferred shares 510 510 Noncontrolling interests 113 186 Total Shareholders’ Equity 5,648 5,160 Total Liabilities, RNCI & Shareholders’ Equity $ 20,913 $ 22,154

Property of Enstar Group – Not for Distribution 29 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 and comparable measurement of the impact of our claims management strategies on our loss portfolios across acquisition years and also to our overall financial periods. We use this measure to evaluate the impact of our claims management strategies because it provides visibility into our ability to settle our claims obligations for amounts less than our initial estimate at the point of acquiring the obligations. The following components of periodic recurring net incurred losses and LAE and net loss reserves are not considered key components of our claims management performance for the following reasons: • Prior to the settlement of the contractual arrangements, the results of our Legacy Underwriting segment were economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement(2); as such, the results were not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies; • The results of our Assumed Life segment relate only to our prior exposure to active property catastrophe business; as this business was not in run-off, the results were not a relevant contribution to Adjusted RLE; • The change in fair value of insurance contracts for which we have elected the fair value option(1) has been removed to support comparability between the two acquisition years for which we elected the fair value option in reserves assumed and the acquisition years for which we did not make this election (specifically, this election was only made in the 2017 and 2018 acquisition years and the election of such option is irrevocable); and • The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis. We include our performance in managing claims and estimated future expenses on our defendant A&E liabilities because such performance is relevant to assessing our claims management strategies even though such liabilities are not included within the loss reserves. 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 Assumed Life operations -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 net ultimate liabilities and reduction in estimated future expenses of our defendant A&E liabilities. Adjusted net loss reserves (denominator) Net losses and LAE, adjusted to: Remove: -Legacy Underwriting and Assumed Life net loss reserves -current period net loss reserves -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 A&E liability exposures and estimated future expenses. (1) Comprises the discount rate and risk margin components. (2) The reinsurance contractual arrangements (including the Capacity Lease Agreement) described in Note 5 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2022 were settled during the second quarter of 2023. As a result of the settlement, we do not expect to record any transactions in the Legacy Underwriting segment in 2023. NON-GAAP MEASURE

Property of Enstar Group – Not for Distribution 30 NON-GAAP MEASURE Non-GAAP Measure Definition Purpose of Non-GAAP Measure over GAAP Measure 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 consistent measure of the performance of our business by enabling comparison between the financial periods presented. We eliminate the impact of net realized and unrealized (gains) losses on fixed maturities and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as: • we typically hold most of our fixed maturities until the earlier of maturity or the time that they are used to fund any settlement of related liabilities which are generally recorded at cost; and • removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option. Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods. We include fair value adjustments as non-GAAP adjustments to the adjusted operating income (loss) attributable to Enstar ordinary shareholders as they are non-cash charges that are not reflective of the impact of our claims management strategies on our loss portfolios. We eliminate the net gain (loss) on the purchase and sales of subsidiaries and net earnings from discontinued operations, as these items are not indicative of our ongoing operations. We use this non-GAAP measure in our incentive compensation program. 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 maturities 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, and -adjustments attributable to noncontrolling interests Adjusted opening Enstar ordinary shareholders' equity (denominator) Opening Enstar ordinary shareholders' equity, less: -net unrealized gains (losses) on fixed maturities 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. We adjust our investment returns to eliminate the impact of the change in fair value of fixed maturities (both credit spreads and interest rates), as we typically hold most of these investments 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 maturities and funds held-directly managed; and -unrealized (gains) losses on fixed maturities, AFS included within OCI, net of reclassification adjustments and excluding foreign exchange. Adjusted average aggregate total investable assets (denominator) Total average investable assets, adjusted for: -net unrealized (gains) losses on fixed maturities, AFS included within AOCI -net unrealized (gains) losses on fixed maturities, trading

Property of Enstar Group – Not for Distribution 31 RECONCILIATION TO ADJUSTED RUN-OFF LIABILITY EARNINGS – 2023 AND 2022 Year Ended As of Year Ended December 31, 2022 December 31, 2022 December 31, 2021 December 31, 2022 December 31, 2022 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % PPD/net loss reserves/RLE % $ 756 $ 12,011 $ 11,926 $ 11,969 6.3 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (45) — (23) Assumed Life (55) — (181) (91) Legacy Underwriting 3 (135) (153) (144) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies (18) 124 106 115 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) (200) 294 107 201 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 2 572 573 573 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 1 35 37 37 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 489 $ 12,856 $ 12,415 $ 12,637 3.9 % (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure. Year Ended As of Year Ended December 31, 2023 December 31, 2023 December 31, 2022 December 31, 2023 December 31, 2023 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % PPD/net loss reserves/RLE % $ 131 $ 11,585 $ 12,011 $ 11,798 1.1 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (30) — (15) Legacy Underwriting — — (139) (69) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 17 107 124 116 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 78 246 294 270 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities (1) 527 572 550 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 2 33 35 34 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 227 $ 12,468 $ 12,897 $ 12,684 1.8 %

Property of Enstar Group – Not for Distribution 32 RECONCILIATION TO ADJUSTED RUN-OFF LIABILITY EARNINGS – 2021 AND 2020 (1) Comprises the discount rate and risk margin components. * Non-GAAP financial measure. Year Ended As of Year Ended December 31, 2021 December 31, 2021 December 31, 2020 December 31, 2021 December 31, 2021 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves Annualized RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 403 $ 11,926 $ 8,763 $ 10,344 3.9 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (143) — (72) Assumed Life — (179) — (90) Legacy Underwriting (6) (140) (955) (548) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 16 106 128 117 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) (75) 107 33 70 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 38 573 615 594 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 5 37 43 40 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 381 $ 12,287 $ 8,627 $ 10,455 3.6 % Year Ended As of Year Ended December 31, 2020 December 31, 2020 December 31, 2019 December 31, 2020 December 31, 2020 RLE / PPD Net loss reserves Net loss reserves Average net loss reserves RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 32 $ 8,763 $ 7,941 $ 8,352 0.4 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (273) — (137) Legacy Underwriting (4) (702) (1,184) (943) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 28 128 152 140 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 119 33 130 82 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 103 615 561 588 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 9 43 52 48 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 287 $ 8,607 $ 7,652 $ 8,129 3.5 %

Property of Enstar Group – Not for Distribution 33 RECONCILIATION TO ADJUSTED RUN-OFF LIABILITY EARNINGS – 2019 (1) Comprises the discount rate and risk margin components. (2) The 2018 balance sheet has not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. * Non-GAAP financial measure. Year Ended As of Year Ended December 31, 2019 December 31, 2019 December 31, 2018 December 31, 2019 December 31, 2019 RLE / PPD Net loss reserves Net loss reserves (2) Average net loss reserves (2) RLE % (in millions of U.S. dollars) PPD/net loss reserves/RLE % $ 4 $ 7,941 $ 7,341 $ 7,641 0.1 % Non-GAAP adjustments for expenses (income): Net loss reserves incurred in the current period — (401) — (201) Legacy Underwriting 106 (842) (1,162) (1,002) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 51 152 199 176 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 117 130 244 187 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 4 561 84 323 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E 3 52 20 36 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE %* $ 285 $ 7,593 $ 6,726 $ 7,160 4.0 %

Property of Enstar Group – Not for Distribution 34 RECONCILIATION TO ADJUSTED RETURN ON EQUITY– 2023, 2022 AND 2021 Year Ended December 31, 2023 December 31, 2022 December 31, 2021 Net income (loss) (1) Opening equity (1)(2) (Adj) ROE Net income (loss) (1) Opening equity (1) (Adj) ROE Net earnings (loss) (1) Opening equity (1) (Adj) ROE Net income (loss)/Opening equity/ROE (1) $ 1,082 $ 4,464 24.2 % $ (906) $ 5,813 (15.6) % $ 502 $ 6,326 7.9 % Non-GAAP adjustments for loss (gains): Net realized losses on fixed maturities, AFS (3) / Net unrealized losses on fixed maturities, AFS (4) 65 647 111 36 4 (82) Net unrealized losses on fixed maturities, trading (3) / Net unrealized losses on fixed maturities, trading (4) (84) 400 503 (134) 144 (384) Net unrealized losses on funds held - directly managed (3) / Net unrealized losses on funds held - directly managed (4) (47) 780 567 9 62 (94) 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 (5) 78 (294) (200) (107) (75) (33) Amortization of fair value adjustments / Fair value adjustments 17 (124) (18) (106) 16 (128) Net gain on purchase and sales of subsidiaries — — — — (73) — Tax effects of adjustments (6) (7) — (7) — (21) — Adjustments attributable to noncontrolling interests (7) (2) — (111) — 6 — Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE* $ 1,102 $ 5,873 18.8 % $ (61) $ 5,511 (1.1) % $ 565 $ 5,605 10.1 % 1) Net income (loss) comprises net income (loss) 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) Enstar ordinary shareholders’ equity as of December 31, 2022 has been retrospectively adjusted for the impact of adopting ASU 2018-12. (3) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations. (4) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance. (5) Comprises the discount rate and risk margin components. (6) 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. (7) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interests associated with the specific subsidiaries to which the adjustments relate. *Non-GAAP measure.

Property of Enstar Group – Not for Distribution 35 RECONCILIATION TO ADJUSTED RETURN ON EQUITY - 2020 AND 2019 Year Ended December 31, 2020 December 31, 2019 Net income (loss) (1) Opening Equity (1) (Adj) ROE Net income (loss) (1) Opening Equity (1) (7) (Adj) ROE Net income (loss)/Opening equity/ROE (1) $ 1,723 $ 4,490 38.4 % $ 906 $ 3,546 25.5 % Non-GAAP adjustments for loss (gains): Net realized losses (gains) on fixed maturities, AFS (2) / Net unrealized losses (gains) on fixed maturities, AFS (3) (18) — (4) (1) Net unrealized (gains) losses on fixed maturities, trading (2) / Net unrealized losses (gains) on fixed maturities, trading (3) (228) (229) (423) 187 Net unrealized (gains) losses on funds held - directly managed (2) / Net unrealized losses (gains) on funds held - directly managed (3) (60) (48) (89) 41 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 (4) 119 (130) 117 (244) Amortization of fair value adjustments / Fair value adjustments 27 (152) 51 (199) Net gain on purchase and sales of subsidiaries (3) — — — Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations (16) (266) (7) (210) Tax effects of adjustments (5) 23 — 36 — Adjustments attributable to noncontrolling interests (6) 13 109 15 86 Adjusted net income (loss)/Adjusted opening equity/Adjusted ROE* $ 1,580 $ 3,774 41.9 % $ 602 $ 3,206 18.8 % (1) Net income (loss) comprises net income (loss) 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) Net realized gains (losses) on fixed maturities, AFS are included in net realized gains (losses) in our consolidated statements of operations. Net unrealized gains (losses) on fixed maturities, trading and funds held - directly managed are included in net unrealized gains (losses) in our consolidated statements of operations. (3) Our fixed maturities are held directly on our balance sheet and also within the "Funds held" balance. (4) Comprises the discount rate and risk margin components. (5) 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. (6) Represents the impact of the adjustments on the net income (loss) attributable to noncontrolling interest associated with the specific subsidiaries to which the adjustments relate. (7) The 2018 balance sheet has not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. * Non-GAAP financial measure.

Property of Enstar Group – Not for Distribution 36 RECONCILIATION TO ADJUSTED TOTAL INVESTMENT RETURN Year Ended December 31, 2023 Net investment income $ 647 Net realized (losses) gains (65) Net unrealized gains (losses) 528 (Losses) income from equity method investments 13 Other comprehensive income: Unrealized gains (losses) on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange 222 TIR ($) $ 1,345 Non-GAAP adjustments: Net unrealized (gains) losses on fixed maturities, trading and funds held-directly managed (66) Unrealized (gains) losses on fixed maturities, AFS, net of reclassification adjustments excluding foreign exchange (222) Adjusted TIR ($)* $ 1,057 Total investments 17,413 Cash and cash equivalents, including restricted cash and cash equivalents 830 Total investable assets $ 18,243 Average aggregate invested assets, at fair value (1) $ 18,607 Annualized TIR % (2) 7.2 % Non-GAAP adjustment: Net unrealized losses (gains) on fixed maturities, AFS included within AOCI and net unrealized losses on fixed maturities, trading and funds held - directly managed 725 Adjusted investable assets* $ 18,968 Adjusted average aggregate invested assets, at fair value* (3) $ 19,769 Annualized adjusted TIR %* (4) 5.3 % (1) This amount is a five period average of the total investable assets for the year ended December 31, 2023, 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 ($) by average aggregate invested assets, at fair value. (3) This amount is a five period average of the adjusted investable assets* for the year ended December 31, 2023, as presented above. (4) Annualized adjusted TIR %* is calculated by dividing the annualized adjusted TIR* ($) by adjusted average aggregate invested assets, at fair value*. *Non-GAAP measure.

Cover Page Cover Page	Feb. 20, 2024
Document Information [Line Items]
Document Type	8-K
Document Period End Date	Feb. 20, 2024
Entity Registrant Name	Enstar Group LTD
Entity File Number	001-33289
Entity Address, Address Line One	A.S. Cooper Building, 4th Floor
Entity Address, Address Line Two	26 Reid Street
Entity Address, City or Town	Hamilton
Entity Address, Postal Zip Code	HM 11
Entity Address, Country	BM
City Area Code	441
Local Phone Number	292-3645
Written Communications	false
Soliciting Material	false
Pre-commencement Tender Offer	false
Pre-commencement Issuer Tender Offer	false
Entity Emerging Growth Company	false
Entity Incorporation, State or Country Code	D0
Entity Central Index Key	0001363829
Amendment Flag	false
Common Stock
Document Information [Line Items]
Title of 12(b) Security	Ordinary shares, par value $1.00 per share
Trading Symbol	ESGR
Security Exchange Name	NASDAQ
Series D Preferred Stock
Document Information [Line Items]
Title of 12(b) Security	Depositary Shares, Each Representing a 1/1,000th Interest in a 7.00% Fixed-to-Floating Rate
Trading Symbol	ESGRP
Security Exchange Name	NASDAQ
Series E Preferred Stock
Document Information [Line Items]
Title of 12(b) Security	Depositary Shares, Each Representing a 1/1,000th Interest
Trading Symbol	ESGRO
Security Exchange Name	NASDAQ

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