# EDGAR Filing Document

**Accession Number:** 0001363829
**File Stem:** 0001363829-23-000021
**Filing Date:** 2023-3
**Character Count:** 180374
**Document Hash:** 1a8d0758d07d8fa4996d1176af318ffe
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001363829-23-000021.hdr.sgml**: 20230301

**ACCESSION NUMBER**: 0001363829-23-000021

**CONFORMED SUBMISSION TYPE**: 8-K

**PUBLIC DOCUMENT COUNT**: 72

**CONFORMED PERIOD OF REPORT**: 20230301

**ITEM INFORMATION**: Results of Operations and Financial Condition

**ITEM INFORMATION**: Regulation FD Disclosure

**ITEM INFORMATION**: Other Events

**FILED AS OF DATE**: 20230301

**DATE AS OF CHANGE**: 20230301

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Enstar Group LTD
- **CENTRAL INDEX KEY:** 0001363829
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **IRS NUMBER:** 999999999
- **STATE OF INCORPORATION:** D0
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** 8-K
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-33289
- **FILM NUMBER:** 23689889

**BUSINESS ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, WINDSOR PLACE, 3RD FL.
- **STREET 2:** 22 QUEEN STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM JX
- **BUSINESS PHONE:** 441-292-3645

**MAIL ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, WINDSOR PLACE, 3RD FL.
- **STREET 2:** 22 QUEEN STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM JX

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Castlewood Holdings LTD
- **DATE OF NAME CHANGE:** 20060523

?xml version="1.0" ? esgr-20230301

**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): March 1, 2023**

**Enstar Group Limited**

**(Exact name of registrant as specified in its charter)**

---

| | | |
|:---|:---|:---|
| **Bermuda** | **001-33289** | **N/A** |
| **(State or other jurisdiction**<br>**of incorporation)** | **(Commission**<br>**File Number)** | **(IRS Employer**<br>**Identification No.)** |

---

**P.O. Box HM 2267, Windsor Place 3**<sup>rd</sup> **Floor** 

**22 Queen Street, Hamilton HM JX Bermuda &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;N/A**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**(Address of principal executive offices) &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; (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:

---

| | | | |
|:---|:---|:---|:---|
| **<u>Title of Each Class</u>** | **<u>Trading Symbol(s)</u>** | **<u>Name of Each Exchange on Which Registered</u>** | **<u>Name of Each Exchange on Which Registered</u>** |
| 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&nbsp;&nbsp;&nbsp;&nbsp;☐

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 March 1, 2023, Enstar Group Limited (the "Company") issued a press release announcing its results for the year ended December 31, 2022 (the "Press Release"), a copy of which is furnished with this report as Exhibit 99.1 and incorporated herein by reference, a Financial Supplement for the year ended December 31, 2022 (the "Financial Supplement"), a copy of which is furnished with this report as Exhibit 99.2 and incorporated herein by reference, and an audio update discussing its results for the year ended December 31, 2022 (the "Audio Update"). The Press Release, the Financial Supplement and the Audio Update will be 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 Audio Update 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 Audio Update, 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 and 99.2 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 7.01. Regulation FD Disclosure.**

On March 1, 2023, the Company released a presentation (the "Investor Presentation"), a copy of which is attached hereto as Exhibit 99.3 and is incorporated herein by reference. The Company expects to use the Investor Presentation from time to time in connection with presentations to potential investors, industry analysts and others. The Investor Presentation is available under the "Events & Presentations" tab of the Company's "Investor Relations" website located at www.enstargroup.com/events-and-presentations.

By filing this Current Report on Form 8-K and furnishing the information in this Item 7.01, the Company makes no admission as to the materiality of any information in the Investor Presentation that is required to be disclosed solely by reason of Regulation FD.

The information contained in the Investor Presentation includes summary information and forward-looking information relating to Enstar's performance that is intended to be considered in the context of the Company's 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 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.

**Item 8.01. Other Events.** 

As previously disclosed, on May 5, 2022, the Company's board of directors authorized the repurchase of up to $200 million of the Company's ordinary shares (the "Repurchase Program"), such authorization to be effective through May 5, 2023. On February 23, 2023, the Company's board of directors authorized the repurchase of up to an additional $105 million of the Company's ordinary shares under the Repurchase Program and extended the authorization effective date through February 23, 2024. Following this increase, the total remaining capacity under the Repurchase Program is now $200 million.

Repurchases pursuant to the Repurchase Program are expected to be executed through open market transactions, privately negotiated transactions, or in such other manner as determined by the

------

Company, including through plans complying with Rule 10b5-1 of the Exchange Act. Repurchases will be subject to SEC regulations as well as certain price, market volume and timing constraints specified in any Rule 10b5-1 plan. As a result of these constraints, execution of the Repurchase Program may not result in all or any of the authorized shares being repurchased by the Company. The Repurchase Program may be modified, extended, suspended or terminated by the Company at any time without notice.

**Item 9.01. Financial Statements and Exhibits**

<u>Exhibits</u>

---

| | |
|:---|:---|
| **Exhibit**<br>**No.** | **Description** |
| <u>[99.1](a2022q4-quarterlypressrele.htm)</u> | Press Release, dated March 1, 2023.  |
| <u>[99.2](a2022q4-investorfinancia.htm)</u> | Financial Supplement for the year ended December 31, 2022. |
| <u>[99.3](enstarq42022investordeck.htm)</u> | Investor 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**

&nbsp;&nbsp;&nbsp;&nbsp;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 | ENSTAR GROUP LIMITED |
| March 1, 2023 | By: | /s/ Orla Gregory |
|  |  | Orla Gregory |
|  |  | Chief Financial Officer |

---

## Exhibit 99.1

**Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;** ![enstarlogo-highres.jpg](enstarlogo-highres.jpg)

**&nbsp;&nbsp;&nbsp;&nbsp;Date:&nbsp;&nbsp;&nbsp;&nbsp;**March 1, 2023**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Contact:** Enstar Communications

**&nbsp;&nbsp;&nbsp;&nbsp;For Release:** Immediately &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Telephone:** +1 (441) 292-3645

**Enstar Group Limited Reports Fourth Quarter and 2022 Year End Results** 

**• Fourth quarter Net Earnings of $227 million and Return on Equity of 5.9%, driven by solid investment income and favorable reserve development of $280 million. Adjusted Return on Equity\*, which excludes unrealized gains and losses, of 4.2%.**

**• Book Value per Ordinary Share increased 8.4% to $246.20 ($243.09 Adjusted\*) as of December 31, 2022.**

**• Closed Loss Portfolio Transfer ("LPT") with Argo and assumed net loss reserves of $718 million.**

**• Substantially completed unwind of Enhanzed Re's reinsurance transactions.**

**• Announced a $1.9 billion global ground-up LPT with QBE and an AUD$360 million LPT with Royal Automobile Club of Queensland covering Motor Compulsory Third Party insurance liabilities in Australia**

HAMILTON, Bermuda - March 1, 2023 - Enstar Group Limited (Nasdaq: ESGR) filed its annual report on Form 10-K with the SEC earlier today. An audio presentation reviewing the fourth quarter and full year 2022 results with expanded commentary is available on Enstar's investor relations website at <u>investor.enstargroup.com</u>.

**Fourth Quarter 2022 Highlights:**

• Net earnings of $227 million, or $13.26 per diluted ordinary share, compared to $120 million, or $6.66 per diluted ordinary share, for the three months ended December 31, 2021.

• Return on equity ("ROE") of 5.9% and Adjusted ROE\* of 4.2% for the quarter compared to 2.1% and 2.5%, respectively, in the fourth quarter of 2021. Net investment income of $153 million and favorable prior period development of $280 million contributed to both ROE and Adjusted ROE\*.

• Our Group regulatory solvency, or economic balance sheet, strengthened during the fourth quarter due to:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ the impact of a higher discount rate on our reserves; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ our core fixed income securities being shorter in duration than our insurance liabilities.

• Run-off liability earnings ("RLE") of $280 million were driven by reductions in the value of certain portfolios that are held at fair value and results from our annual loss reserve reviews where we recorded favorable development on 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. RLE was impacted by adverse development on our general casualty and motor lines of business.

• Annualized total investment return ("TIR") of 3.5% and Annualized Adjusted TIR\* of 1.9%, compared to 1.0% and 2.0%, respectively, for the three months ended December 31, 2021. Recognized investment results benefited from an increase in net investment income of $72 million.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1

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• Completed a LPT agreement with a wholly-owned subsidiary of Argo Group International Holdings, Ltd. ("Argo").

\* 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 are pleased to report strong fourth quarter results as we grew book value by 8.4% providing us with a positive end to a challenging 2022. While our annual performance was impacted by headwinds in the investment markets, our claims management function continues to outperform the industry driving prior period reserve savings of $756 million for the year.

2022 was another record M&A year as we acquired $2.7 billion of incremental reserves, including completing and integrating one of our largest-ever loss portfolio transfers with Aspen. That activity has continued into 2023, as we just announced a $1.9 billion ground up LPT with QBE, and a second AUD$360 million transaction with Royal Automobile Club of Queensland. We remain well-positioned to capitalize on our robust pipeline so long as opportunities align with our risk parameters and return hurdles.

We expect to continue as the dominant player in the legacy market in 2023. Our balance sheet remains strong, and our scale, operational capabilities, and highly differentiated claims expertise will support accretive opportunities with new and long-standing partners while driving long-term value to our shareholders."

**Year ended December 31, 2022 Highlights:**

• Net loss of $906 million, or $52.65 per diluted ordinary share, compared to net earnings of $502 million, or $24.94 per diluted ordinary share, for the year ended December 31, 2021.

• ROE of (15.6)% and Adjusted ROE\* of (1.1)%, compared to 7.9% and 10.1%, respectively, for the year ended December 31, 2021. ROE was impacted by unrealized losses arising from interest rate increases on fixed maturity portfolios that are classified as trading combined with unrealized losses in Enstar's non-core portfolios.

• RLE of 6.3% and Adjusted RLE\* of 3.9%, compared to 3.9% and 3.6%, respectively, for the year ended December 31, 2021. RLE benefited from reductions in the value of certain portfolios that are held at fair value, favorable development on our workers' compensation, marine, aviation and transit lines of business, and favorable results on Enstar's inactive catastrophe programs held by Enhanzed Re, including the recognition of a gain on commutation of the reserves. RLE was impacted by adverse development on our general casualty and motor lines of business.

• TIR of (9.0)% and Adjusted TIR\* of (0.2)%, compared to 2.0% and 3.6%, respectively, for the year ended December 31, 2021. Recognized investment results were impacted by the combination of interest rate increases, widening credit spreads and equity market declines.

• Completed LPT agreements with Aspen Insurance Holdings Limited and Argo totaling $2.7 billion of incremental acquired reserves.

• Completed commutation of Enhanzed Re's catastrophe book and novated Enhanzed Re's portfolio of deferred annuities and whole life policies.

\* 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 \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2

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**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** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** |
| | **December 31, 2022** | **December 31, 2021** | **$/ pp / bp Change** | **$/ pp / bp Change** | **December 31, 2020** | **$/ pp / bp Change** | **$/ pp / bp Change** |
| | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** | **(in millions of U.S. dollars, except per share data)** |
| **Key Earnings Metrics** | | | | | | | |
| &nbsp;&nbsp;&nbsp;Net (loss) earnings attributable to Enstar ordinary shareholders | $(906) | $502 | $(1408) |  | $1723 | $(1221) |  |
| &nbsp;&nbsp;&nbsp;Adjusted operating (loss) income attributable to Enstar ordinary shareholders\* | $(61) | $565 | $(626) |  | $1580 | $(1015) |  |
| &nbsp;&nbsp;&nbsp;ROE | (15.6)% | 7.9% | (23.5) | pp | 38.4% | (30.5) | pp |
| &nbsp;&nbsp;&nbsp;Adjusted ROE\* | (1.1)% | 10.1% | (11.2) | pp | 41.9% | (31.8) | pp |
| **Key Run-off Metrics** |  |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Prior period development | $756 | $403 | $353 |  | $32 | $371 |  |
| &nbsp;&nbsp;&nbsp;Adjusted prior period development\* | $489 | $381 | $108 |  | $287 | $94 |  |
| &nbsp;&nbsp;&nbsp;RLE | 6.3% | 3.9% | 2.4 | pp | 0.4% | 3.5 | pp |
| &nbsp;&nbsp;&nbsp;Adjusted RLE\* | 3.9% | 3.6% | 0.3 | pp | 3.5% | 0.1 | pp |
| **Key Investment Return Metrics** |  |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Total investable assets | $19540 | $21708 | $(2168) |  | $17266 | $4442 |  |
| &nbsp;&nbsp;&nbsp;Adjusted total investable assets\* | $21367 | $21619 | $(252) |  | $16706 | $4913 |  |
| &nbsp;&nbsp;&nbsp;Investment book yield | 2.47% | 1.84% | 63 | bp | 2.53% | (69) | bp |
| &nbsp;&nbsp;&nbsp;TIR | (9.0)% | 2.0% | (11.0) | pp | 14.6% | (12.6) | pp |
| &nbsp;&nbsp;&nbsp;Adjusted TIR\* | (0.2)% | 3.6% | (3.8) | pp | 12.4% | (8.8) | pp |
| **Key Shareholder Metrics** |  |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Book value per ordinary share | $246.20 | $329.20 | $(83.00) |  | $293.97 | $35.23 |  |
| &nbsp;&nbsp;&nbsp;Adjusted book value per ordinary share\* | $243.09 | $323.43 | $(80.34) |  | $288.56 | $34.87 |  |

---

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 \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;3

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**Results of Operations By Segment - For the Years Ended December 31, 2022, 2021 and 2020**

**<u>Run-off Segment</u>**

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

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **2022** | **2021** | **Change** | **2020** | **Change** |
| INCOME | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| Net premiums earned | $40 | $182 | $(142) | $59 | $123 |
| Other income: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Reduction in estimates of net ultimate defendant A&E liabilities - prior periods | 2 | 38 | (36) | 103 | (65) |
| &nbsp;&nbsp;&nbsp;Reduction in estimated future defendant A&E expenses | 1 | 5 | (4) | 9 | (4) |
| &nbsp;&nbsp;&nbsp;All other income | 19 | 30 | (11) | 20 | 10 |
| Total other income | 22 | 73 | (51) | 132 | (59) |
| Total income | 62 | 255 | (193) | 191 | 64 |
| EXPENSES |  |  |  |  |  |
| Net incurred losses and LAE: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Current period | 44 | 144 | (100) | 30 | 114 |
| &nbsp;&nbsp;&nbsp;Prior period | (486) | (338) | (148) | (175) | (163) |
| Total net incurred losses and LAE | (442) | (194) | (248) | (145) | (49) |
| Acquisition costs | 22 | 44 | (22) | 20 | 24 |
| General and administrative expenses | 143 | 188 | (45) | 173 | 15 |
| Total expenses | (277) | 38 | (315) | 48 | (10) |
| SEGMENT NET EARNINGS | $339 | $217 | $122 | $143 | $74 |

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

<sup>•</sup> A $148 million increase in favorable PPD, driven by a $78 million increase in the reduction in estimates of net ultimate losses.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<sup>◦</sup> 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

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ 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.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<sup>◦</sup> 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 net premiums earned that were greater than the reductions in current period net incurred losses and LAE and acquisition costs, following our exit of our StarStone International business beginning in 2020.

**2021 versus 2020:** Net earnings from our Run-off segment increased by $74 million, primarily due to:

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4

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• Net premiums earned increased by $123 million from StarStone International business and new business transactions executed in recent periods. Net premiums earned of $182 million included $106 million of premiums from StarStone International, which was transferred into the Run-off Segment on January 1, 2021, whereas net premiums earned in 2020 were primarily related to AmTrust RITC transactions assumed in 2019.

• Net incurred losses and LAE decreased by $49 million due to a $163 million increase in favorable PPD partially offset by an increase in current period losses of $114 million due to the transfer of the StarStone International business from the Legacy Underwriting segment on January 1, 2021.

• The $163 million increase in favorable PPD primarily consists of:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ $51 million increase in favorable development on the workers' compensation line of business in 2021 as a result of reduced claims activity, favorable settlements on open claims and the completion of commutations;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ $105 million reduction in adverse development on the motor line of business compared to 2020. 2020 was impacted by higher than expected severity in respect of a recently assumed LPT;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ $41 million increase in favorable development on the construction defect line of business in 2021; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;◦ $82 million increase in favorable development on the property and other lines of business in 2021.

This favorable prior period developments were partially offset by;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• $142 million increases in prior period estimates of net ultimate losses in our general casualty line of business due to an increase in opioid exposure and greater than expected adverse development.

In addition:

• Other income decreased by $59 million primarily driven by lower favorable prior period development related to our defendant A&E liabilities; and

• Acquisition costs increased by $24 million primarily due to the transfer of StarStone International from the Legacy Underwriting segment on January 1, 2021.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;5

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**<u>Investments Segment</u>**

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

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **2022** | **2021** | **Change** | **2020** | **Change** |
| INCOME | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| Net investment income: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Fixed income securities | $380 | $273 | $107 | $243 | $30 |
| &nbsp;&nbsp;&nbsp;Cash and restricted cash | 8 |  | 8 | 2 | (2) |
| &nbsp;&nbsp;&nbsp;Other investments, including equities | 82 | 73 | 9 | 39 | 34 |
| &nbsp;&nbsp;&nbsp;Less: Investment expenses | (25) | (37) | 12 | (14) | (23) |
| Total net investment income | 445 | 309 | 136 | 270 | 39 |
| Net realized (losses) gains: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Fixed income securities | (111) | (4) | (107) | 16 | (20) |
| &nbsp;&nbsp;&nbsp;Other investments, including equities | (24) | (57) | 33 | 1 | (58) |
| Total net realized (losses) gains | (135) | (61) | (74) | 17 | (78) |
| Net unrealized (losses) gains: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Fixed income securities, trading | (1060) | (203) | (857) | 284 | (487) |
| &nbsp;&nbsp;&nbsp;Other investments, including equities | (409) | 384 | (793) | 1327 | (943) |
| Total net unrealized (losses) gains | (1469) | 181 | (1650) | 1611 | (1430) |
| Total income | (1159) | 429 | (1588) | 1898 | (1469) |
| EXPENSES |  |  |  |  |  |
| General and administrative expenses | 37 | 37 |  | 35 | 2 |
| Total expenses | 37 | 37 |  | 35 | 2 |
| (Losses) earnings from equity method investments | (74) | 93 | (167) | 239 | (146) |
| SEGMENT NET (LOSS) EARNINGS | $(1270) | $485 | $(1755) | $2102 | $(1617) |

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**<u>Overall Results</u>**

**2022 versus 2021:** Net loss from our Investments segment was $1.3 billion compared to net earnings 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;

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

***•*** Losses from equity method investments of $74 million, in comparison to earnings of $93 million in 2021, primarily due to the recognition of an other-than-temporary impairment to the carrying value of one of our equity method investments 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 earnings 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 earnings 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 income securities at higher yields and the impact of rising interest rates on the $2.9 billion of our fixed income securities 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 income securities that support our Enhanzed Re life reinsurance business for the years ended December 31, 2022 and 2021 were $304 million $332 millionand $17 million, respectively.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;6

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**2021 versus 2020:** Net earnings from our Investments segment decreased by $1.6 billion primarily as a result of decreases in net realized and unrealized gains of $1.5 billion. The decrease is largely a result of 2021 net realized and unrealized losses of $58 million related to the InRe Fund, in comparison to net unrealized gains of $1.2 billion in 2020, and 2021 net realized and unrealized losses on our fixed income securities of $207 million, in comparison to net realized and unrealized gains of $300 million in 2020.

**Income and (Loss) Earnings by Segment - For the Years Ended December 31, 2022, 2021 and 2020**

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** |
| | **December 31, 2022** | **December 31, 2021** | **$ Change** | | **December 31, 2020** | **$ Change** |
| | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| INCOME |  |  |  |  |  |  |
| Run-off | $62 | $255 | $(193) |  | $191 | $64 |
| Assumed Life | 17 | 5 | 12 |  |  | 5 |
| Investments | (1159) | 429 | (1588) |  | 1898 | (1469) |
| Legacy Underwriting | 10 | 43 | (33) |  | 587 | (544) |
| Subtotal | (1070) | 732 | (1802) |  | 2676 | (1944) |
| Corporate and other | 12 | 57 | (45) |  | $(16) | 73 |
| Total income | $(1058) | $789 | $(1847) | $— | $2660 | $(1871) |
| SEGMENT NET (LOSS) EARNINGS |  |  |  |  |  |  |
| Run-off | $339 | $217 | $122 |  | $143 | $74 |
| Assumed Life | 40 | 6 | 34 |  |  | 6 |
| Investments | (1270) | 485 | (1755) |  | 2102 | (1617) |
| Legacy Underwriting |  |  |  |  | (93) | 93 |
| Total segment net (loss) earnings | (891) | 708 | (1599) |  | 2152 | (1444) |
| Corporate and other <sup>(1)</sup> | (15) | (206) | 191 |  | (429) | 223 |
| NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS | $(906) | $502 | $(1408) |  | $1723 | $(1221) |

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<sup>(1)</sup> Other income (expense) for corporate and other activities includes the amortization of fair value adjustments associated with the acquisition of DCo LLC and Morse TEC LLC.

For additional detail on the Assumed Life segment, the Legacy Underwriting segment and Corporate and other activities, please refer to our Annual Report on Form 10-K for the year ended December 31, 2022.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;7

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**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', 'ambition', '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, 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, Australia, and other international locations. A market leader in completing legacy acquisitions, Enstar has acquired over 110 companies and portfolios since its formation in 2001. For further information about Enstar, see <u>www.enstargroup.com</u>.

**Contacts**

**<u>For Investors:</u>** Matthew Kirk (investor.relations@enstargroup.com)

**<u>For Media:</u>** Jenna Kerr (communications@enstargroup.com)

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;8

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**ENSTAR GROUP LIMITED**

**CONSOLIDATED STATEMENTS OF EARNINGS**

**For the Three Months Ended December 31, 2022 and 2021 and the Years Ended December 31, 2022, 2021, and 2020**

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended<br>December 31,** | **Three Months Ended<br>December 31,** | **Year Ended December 31,** | **Year Ended December 31,** | **Year Ended December 31,** |
| | **2022** | **2021** | **2022** | **2021** | **2020** |
| | **(expressed in millions of U.S. dollars, except share and per share data)** | **(expressed in millions of U.S. dollars, except share and per share data)** | **(expressed in millions of U.S. dollars, except share and per share data)** | **(expressed in millions of U.S. dollars, except share and per share data)** | **(expressed in millions of U.S. dollars, except share and per share data)** |
| INCOME |  |  |  |  |  |
| Net premiums earned | $14 | $41 | $66 | $245 | $572 |
| Net investment income | 153 | 81 | 455 | 312 | 303 |
| Net realized (losses) gains | (24) | (62) | (135) | (61) | 19 |
| Net unrealized (losses) gains | 39 | 68 | (1479) | 178 | 1623 |
| Other income | 2 | 15 | 35 | 42 | 140 |
| Net gain on purchase and sales of subsidiaries |  | 11 |  | 73 | 3 |
| Total income | 184 | 154 | (1058) | 789 | 2660 |
| EXPENSES |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net incurred losses and loss adjustment expenses |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Current Period | 9 | 26 | 48 | 172 | 405 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Prior Period | (280) | (159) | (756) | (403) | (32) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Total net incurred losses and loss adjustment expenses | (271) | (133) | (708) | (231) | 373 |
| &nbsp;&nbsp;&nbsp;Policyholder benefit expenses |  | (3) | 25 | (3) |  |
| &nbsp;&nbsp;&nbsp;Amortization of net deferred charge assets | 20 | 17 | 80 | 55 | 39 |
| &nbsp;&nbsp;&nbsp;Acquisition costs | 3 | 7 | 23 | 57 | 171 |
| &nbsp;&nbsp;&nbsp;General and administrative expenses | 97 | 98 | 331 | 367 | 502 |
| &nbsp;&nbsp;&nbsp;Interest expense | 18 | 18 | 89 | 69 | 59 |
| &nbsp;&nbsp;&nbsp;Net foreign exchange (gains) losses | 12 | (3) | (15) | (12) | 16 |
| &nbsp;&nbsp;&nbsp;Total expenses | (121) | 1 | (175) | 302 | 1160 |
| (LOSS) EARNINGS BEFORE INCOME TAXES | 305 | 153 | (883) | 487 | 1500 |
| Income tax benefit (expense) | 16 | (14) | 12 | (27) | (24) |
| (Losses) earnings from equity method investments | (86) | (8) | (74) | 93 | 239 |
| NET (LOSS) EARNINGS FROM CONTINUING OPERATIONS | 235 | 131 | (945) | 553 | 1715 |
| Net earnings from discontinued operations, net of income taxes |  |  |  |  | 16 |
| NET (LOSS) EARNINGS | 235 | 131 | (945) | 553 | 1731 |
| Net loss (earnings) attributable to noncontrolling interest | 1 | (2) | 75 | (15) | 28 |
| NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR | 236 | 129 | (870) | 538 | 1759 |
| Dividends on preferred shares | (9) | (9) | (36) | (36) | (36) |
| NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS | $227 | $120 | $(906) | $502 | $1723 |
| (Loss) earnings per ordinary share attributable to Enstar: | (Loss) earnings per ordinary share attributable to Enstar: | (Loss) earnings per ordinary share attributable to Enstar: |  |  |  |
| &nbsp;&nbsp;&nbsp;Basic |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net (loss) earnings from continuing operations | $13.34 | $6.74 | $(52.65) | $25.33 | $79.60 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net earnings from discontinued operations |  |  |  |  | 0.35 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net (loss) earnings per ordinary share | $13.34 | $6.74 | $(52.65) | $25.33 | $79.95 |
| &nbsp;&nbsp;&nbsp;Diluted |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net (loss) earnings from continuing operations | $13.26 | $6.66 | $(52.65) | $24.94 | $78.62 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net earnings from discontinued operations |  |  |  |  | 0.35 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net (loss) earnings per ordinary share | $13.26 | $6.66 | $(52.65) | $24.94 | $78.97 |
| Weighted average ordinary shares outstanding: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Basic | 17021348 | 17798994 | 17207229 | 19821259 | 21551408 |
| &nbsp;&nbsp;&nbsp;Diluted | 17121606 | 18013284 | 17323130 | 20127131 | 21818294 |

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**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;9

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**ENSTAR GROUP LIMITED**

**CONSOLIDATED BALANCE SHEETS**

**As of December 31, 2022 and December 31, 2021** 

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| | | |
|:---|:---|:---|
| | **December 31, 2022** | **December 31, 2021** |
| | **(in millions of U.S. dollars, except share data)** | **(in millions of U.S. dollars, except share data)** |
| **ASSETS** | | |
| Short-term investments, trading, at fair value | $14 | $6 |
| Short-term investments, available-for-sale, at fair value (amortized cost: 2022 — $37; 2021 — $34) | 38 | 34 |
| Fixed maturities, trading, at fair value | 2370 | 3756 |
| Fixed maturities, available-for-sale, at fair value (amortized cost: 2022 — $5,871; 2021 — $5,689; net of allowance: 2022 — $33; 2021 — $10) | 5223 | 5652 |
| Funds held - directly managed, at fair value | 2040 | 3007 |
| Equities, at fair value (cost: 2022 — $1,357; 2021 — $1,831) | 1250 | 1995 |
| Other investments, at fair value (includes $3 in 2022 of consolidated variable interest entities) | 3296 | 2333 |
| Equity method investments | 397 | 493 |
| Total investments | 14628 | 17276 |
| Cash and cash equivalents | 822 | 1646 |
| Restricted cash and cash equivalents | 508 | 446 |
| Reinsurance balances recoverable on paid and unpaid losses (net of allowance: 2022 — $131; 2021 — $136) | 856 | 1085 |
| Reinsurance balances recoverable on paid and unpaid losses, at fair value | 275 | 432 |
| Insurance balances recoverable (net of allowance: 2022 and 2021 — $5) | 177 | 213 |
| Funds held by reinsured companies | 3582 | 2340 |
| Net deferred charge assets | 658 | 598 |
| Other assets | 648 | 620 |
| TOTAL ASSETS | $22154 | $24656 |
| **LIABILITIES** |  |  |
| Losses and loss adjustment expenses | $11721 | $11269 |
| Losses and loss adjustment expenses, at fair value | 1286 | 1989 |
| Future policyholder benefits | 1184 | 1502 |
| Defendant asbestos and environmental liabilities | 607 | 638 |
| Insurance and reinsurance balances payable | 100 | 254 |
| Debt obligations | 1829 | 1691 |
| Other liabilities | 462 | 581 |
| TOTAL LIABILITIES | 17189 | 17924 |
| **COMMITMENTS AND CONTINGENCIES** |  |  |
| **REDEEMABLE NONCONTROLLING INTERESTS** | 168 | 179 |
| **SHAREHOLDERS' EQUITY** |  |  |
| Ordinary Shares (par value $1 each, issued and outstanding 2022: 17,588,050; 2021: 18,223,574): |  |  |
| &nbsp;&nbsp;&nbsp;Voting Ordinary Shares (issued and outstanding 2022: 15,990,338; 2021: 16,625,862) | 16 | 17 |
| &nbsp;&nbsp;&nbsp;Non-voting convertible ordinary Series C Shares (issued and outstanding 2022 and 2021: 1,192,941) | 1 | 1 |
| &nbsp;&nbsp;&nbsp;Non-voting convertible ordinary Series E Shares (issued and outstanding 2022 and 2021: 404,771) |  |  |
| Preferred Shares: |  |  |
| &nbsp;&nbsp;&nbsp;Series C Preferred Shares (issued and held in treasury 2022 and 2021: 388,571) |  |  |
| &nbsp;&nbsp;&nbsp;Series D Preferred Shares (issued and outstanding 2022 and 2021: 16,000; liquidation preference $400) | 400 | 400 |
| &nbsp;&nbsp;&nbsp;Series E Preferred Shares (issued and outstanding 2022 and 2021: 4,400; liquidation preference $110) | 110 | 110 |
| Treasury shares, at cost (Series C Preferred Shares 2022 and 2021: 388,571) | (422) | (422) |
| Joint Share Ownership Plan (voting ordinary shares, held in trust 2022 and 2021: 565,630) | (1) | (1) |
| Additional paid-in capital | 766 | 922 |
| Accumulated other comprehensive loss | (575) | (16) |
| Retained earnings | 4406 | 5312 |
| Total Enstar Shareholders' Equity | 4701 | 6323 |
| Noncontrolling interests | 96 | 230 |
| TOTAL SHAREHOLDERS' EQUITY | 4797 | 6553 |
| TOTAL LIABILITIES, REDEEMABLE NONCONTROLLING INTERESTS AND SHAREHOLDERS' EQUITY | $22154 | $24656 |

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**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;10

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**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 income securities 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 investment 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.

We have changed our non-GAAP measures in 2022 as follows:

• The opening GAAP balances of our 2021 and 2020 Adjusted BVPS\*, Adjusted ROE\* and Adjusted RLE\* measures have been retrospectively adjusted for a change in accounting principle.

• We no longer remove ULAE from our Adjusted RLE and RLE % calculations as our estimate of future claims handling costs is connected to our claims settlement strategies and outcomes and the RLE measures now reflect the direct and indirect performance of the management of our liabilities.

We have presented the results and GAAP reconciliations for these measures further below. The following tables present more information on each non-GAAP measure.

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| | | |
|:---|:---|:---|
| **Non-GAAP Measure** | **Definition** | **Purpose of Non-GAAP Measure over GAAP Measure** |
| **<u>Adjusted book value per ordinary share</u>** | Total Enstar ordinary shareholders' equity<br>Divided by<br>Number of ordinary shares outstanding, adjusted for:<br>-*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. <br>We use this non-GAAP measure in our incentive compensation program.  |

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**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;11

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| | | |
|:---|:---|:---|
| **<u>Adjusted return on equity (%)</u>** | 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. <br>We eliminate the impact of net realized and unrealized (gains) losses on fixed maturity investments and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as: <br>• we typically hold most of our fixed income securities 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 <br>• removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option. <br>Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods.&nbsp;&nbsp;&nbsp;&nbsp;<br>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. <br>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. <br>We use this non-GAAP measure in our incentive compensation program. |
| **Adjusted operating income (loss) attributable to Enstar ordinary shareholders**<br>**(*numerator)*** | Net earnings (loss) attributable to Enstar ordinary shareholders, adjusted for:<br>*-net realized and unrealized (gains) losses on fixed maturity investments and funds held-directly managed,*<br>*-change in fair value of insurance contracts for which we have elected the fair value option* <sup>(1)</sup>*,*<br>*-amortization of fair value adjustments,*<br>*-net gain/loss on purchase and sales of subsidiaries (if any),*<br>*-net earnings from discontinued operations (if any),*<br>*-tax effects of adjustments, and*<br>*-adjustments attributable to noncontrolling interests* | 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. <br>We eliminate the impact of net realized and unrealized (gains) losses on fixed maturity investments and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as: <br>• we typically hold most of our fixed income securities 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 <br>• removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option. <br>Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods.&nbsp;&nbsp;&nbsp;&nbsp;<br>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. <br>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. <br>We use this non-GAAP measure in our incentive compensation program. |
| **Adjusted opening Enstar ordinary shareholders' equity (*denominator)*** | Opening Enstar ordinary shareholders' equity, less:<br>*-net unrealized gains (losses) on fixed maturity investments and funds held-directly managed,*<br>*-fair value of insurance contracts for which we have elected the fair value option* <sup>(1)</sup>*,*<br>*-fair value adjustments, and*<br>*-net assets of held for sale or disposed subsidiaries classified as discontinued operations (if any)* | 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. <br>We eliminate the impact of net realized and unrealized (gains) losses on fixed maturity investments and funds-held directly managed and the change in fair value of insurance contracts for which we have elected the fair value option, as: <br>• we typically hold most of our fixed income securities 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 <br>• removing the fair value option improves comparability since there are limited acquisition years for which we elected the fair value option. <br>Therefore, we believe that excluding their impact on our earnings improves comparability of our core operational performance across periods.&nbsp;&nbsp;&nbsp;&nbsp;<br>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. <br>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. <br>We use this non-GAAP measure in our incentive compensation program. |
| **<u>Adjusted total investment return (%)</u>** | 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. <br>Provides a consistent measure of investment returns as a percentage of all assets generating investment returns. <br>We adjust our investment returns to eliminate the impact of the change in fair value of fixed income securities (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:<br>*-net realized and unrealized (gains) losses on fixed maturity investments and funds held-directly managed; and*<br>*-unrealized (gains) losses on AFS investments included within OCI, net of reclassification adjustments and excluding foreign exchange.*  | Provides a key measure of the return generated on the capital held in the business and is reflective of our investment strategy. <br>Provides a consistent measure of investment returns as a percentage of all assets generating investment returns. <br>We adjust our investment returns to eliminate the impact of the change in fair value of fixed income securities (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 average aggregate total investable assets (*denominator*)** | Total average investable assets, adjusted for: <br>*-net unrealized (gains) losses on fixed maturities, AFS investments included within AOCI*<br>*-net unrealized (gains) losses on fixed maturities, trading instruments* | Provides a key measure of the return generated on the capital held in the business and is reflective of our investment strategy. <br>Provides a consistent measure of investment returns as a percentage of all assets generating investment returns. <br>We adjust our investment returns to eliminate the impact of the change in fair value of fixed income securities (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. |

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**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;12

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| | | |
|:---|:---|:---|
| **<u>Adjusted run-off liability earnings (%)</u>** | Adjusted PPD divided by average adjusted net loss reserves | &nbsp;&nbsp;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. <br>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.&nbsp;&nbsp;&nbsp;&nbsp;<br>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: <br>• The results of our Legacy Underwriting segment have been economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement<sup>(2)</sup>; as such, the results are not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies; <br>• The results of our Assumed Life segment relate only to our exposure to active property catastrophe business; as this business is not in run-off, the results are not a relevant contribution to Adjusted RLE; <br>• The change in fair value of insurance contracts for which we have elected the fair value option<sup>(1)</sup> 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<br>• The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis.<br>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.<br>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**<br>***(numerator)*** | Prior period net incurred losses and LAE, adjusted to: <br>*Remove*<sup>(3)</sup>*:* <br>*-*Legacy Underwriting *and* Assumed Life *operations* <br>*-amortization of fair value adjustments,* <br>*-change in fair value of insurance contracts for which we have elected the fair value option* <sup>(1)</sup>*,* <br>*and* <br>*Add:* <br>*-the reduction/(increase) in estimates of net ultimate liabilities and reduction in estimated future expenses of our defendant A&E liabilities.*  | &nbsp;&nbsp;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. <br>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.&nbsp;&nbsp;&nbsp;&nbsp;<br>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: <br>• The results of our Legacy Underwriting segment have been economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement<sup>(2)</sup>; as such, the results are not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies; <br>• The results of our Assumed Life segment relate only to our exposure to active property catastrophe business; as this business is not in run-off, the results are not a relevant contribution to Adjusted RLE; <br>• The change in fair value of insurance contracts for which we have elected the fair value option<sup>(1)</sup> 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<br>• The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis.<br>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.<br>We use this measure to assess the performance of our claim strategies and part of the performance assessment of our past acquisitions. |
| **Adjusted net loss reserves** <br>***(denominator)*** | Net losses and LAE, adjusted to:<br>*Remove*<sup>(3)</sup>*:*<br>*-*Legacy Underwriting *and* Assumed Life *net loss reserves*<br>*-current period net loss reserves*<br>*-net fair value adjustments associated with the acquisition of companies,*<br>*-the fair value adjustments for contracts for which we have elected the fair value option* <sup>(1)</sup> *and*<br>*Add:*<br>*-net nominal defendant A&E liability exposures and estimated future expenses* | &nbsp;&nbsp;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. <br>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.&nbsp;&nbsp;&nbsp;&nbsp;<br>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: <br>• The results of our Legacy Underwriting segment have been economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement<sup>(2)</sup>; as such, the results are not a relevant contribution to Adjusted RLE, which is designed to analyze the impact of our claims management strategies; <br>• The results of our Assumed Life segment relate only to our exposure to active property catastrophe business; as this business is not in run-off, the results are not a relevant contribution to Adjusted RLE; <br>• The change in fair value of insurance contracts for which we have elected the fair value option<sup>(1)</sup> 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<br>• The amortization of fair value adjustments are non-cash charges that obscure our trends on a consistent basis.<br>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.<br>We use this measure to assess the performance of our claim strategies and part of the performance assessment of our past acquisitions. |

---

<sup>(1) &nbsp;&nbsp;&nbsp;&nbsp;</sup>Comprises the discount rate and risk margin components.

<sup>(2) &nbsp;&nbsp;&nbsp;&nbsp;</sup>As described in Note 5 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2022.

<sup>(3) &nbsp;&nbsp;&nbsp;&nbsp;</sup>Effective for 2022, we are no longer excluding ULAE as it relates to our losses and LAE liabilities and are now including estimated future expenses as it relates to our defendant A&E liabilities in the calculation of Adjusted RLE\*, as these provisions are related to our insurance liabilities and contribute to our claims management performance. The comparative periods in 2021 and 2020 have been adjusted accordingly.

\*Non-GAAP measure.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;13

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**Reconciliation of GAAP to Non-GAAP Measures**

The table below presents a reconciliation of BVPS to Adjusted BVPS\*:

---

| | | | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|
| | **December 31, 2022** | **December 31, 2022** | **December 31, 2022** | **December 31, 2021** | **December 31, 2021** | **December 31, 2021** | **December 31, 2020** | **December 31, 2020** | **December 31, 2020** |
| | **Equity** <sup>(1)</sup> | **Ordinary Shares** | **Per Share Amount** | **Equity** <sup>(1)</sup> | **Ordinary Shares** | **Per Share Amount** | **Equity** <sup>(1)</sup> | **Ordinary Shares** | **Per Share Amount** |
| | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** | **(in millions of U.S. dollars, except share and per share data)** |
| **Book value per ordinary share** | $4191 | 17022420 | $246.20 | $5813 | 17657944 | $329.20 | $6326 | 21519602 | $293.97 |
| Non-GAAP adjustment: |  |  |  |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Share-based compensation plans |  | 218171 |  |  | 315205 |  |  | 298095 |  |
| &nbsp;&nbsp;&nbsp;Warrants |  |  |  |  |  |  | 20 | 175901 |  |
| **Adjusted book value per ordinary share\*** | $4191 | 17240591 | $243.09 | $5813 | 17973149 | $323.43 | $6346 | 21993598 | $288.56 |

---

<sup>(1)</sup> Equity comprises Enstar ordinary shareholders' equity, which is calculated as Enstar shareholders' equity less preferred shares ($510 million) prior to any non-GAAP adjustments.

\*Non-GAAP measure.

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

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended** | **Three Months Ended** | **Three Months Ended** | **Three Months Ended** | **Three Months Ended** | **Three Months Ended** |
| | **December 31, 2022** | **December 31, 2022** | **December 31, 2022** | **December 31, 2021** | **December 31, 2021** | **December 31, 2021** |
| | **Net (loss) earnings** <sup>(1)</sup> | **Opening equity** <sup>(1)</sup> | **(Adj) ROE** | **Net (loss) earnings** <sup>(1)</sup> | **Opening equity** <sup>(1)</sup> | **(Adj) ROE** |
| | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| **Net (loss) earnings/Opening equity/ROE**<sup>(1)</sup> | $227 | $3866 | 5.9% | $120 | $5749 | 2.1% |
| Non-GAAP adjustments: |  |  |  |  |  |  |
| *Remove:* |  |  |  |  |  |  |
| &nbsp;&nbsp;Net realized and unrealized losses (gains) on fixed maturity investments and funds held - directly managed / Net unrealized losses (gains) on fixed maturity investments and funds held - directly managed <sup>(2)</sup> | 20 | 1926 |  | 27 | (176) |  |
| &nbsp;&nbsp;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 <sup>(3)</sup> | 28 | (305) |  | (6) | (100) |  |
| &nbsp;&nbsp;&nbsp;Amortization of fair value adjustments / Fair value adjustments | (29) | (95) |  | 3 | (109) |  |
| &nbsp;&nbsp;&nbsp;Net gain on purchase and sales of subsidiaries |  |  |  | (11) |  |  |
| &nbsp;&nbsp;Tax effects of adjustments <sup>(4)</sup> | (1) |  |  | (3) |  |  |
| &nbsp;&nbsp;Adjustments attributable to noncontrolling interests <sup>(5)</sup> | (21) |  |  | 2 |  |  |
| **Adjusted operating (loss) income/Adjusted opening equity/Adjusted ROE\*** | $224 | $5392 | 4.2% | $132 | $5364 | 2.5% |

---

<sup>(1)</sup> 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.

<sup>(2)</sup> 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.

<sup>(3)</sup> Comprises the discount rate and risk margin components.

<sup>(4)</sup> 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.

<sup>(5)</sup> 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 measure.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;14

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---

| | | | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|
| | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** | **Year Ended** |
| | **December 31, 2022** | **December 31, 2022** | **December 31, 2022** | **December 31, 2021** | **December 31, 2021** | **December 31, 2021** | **December 31, 2020** | **December 31, 2020** | **December 31, 2020** |
| | **Net (loss) earnings** <sup>(1)</sup> | **Opening equity** <sup>(1)</sup> | **(Adj) ROE** | **Net (loss) earnings** <sup>(1)</sup> | **Opening equity** <sup>(1)</sup> | **(Adj) ROE** | **Net (loss) earnings** <sup>(1)</sup> | **Opening equity** <sup>(1)</sup> | **(Adj) ROE** |
| | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| **Net (loss) earnings/Opening equity/ROE** <sup>(1)</sup> | $(906) | $5813 | (15.6)% | $502 | $6326 | 7.9% | $1723 | $4490 | 38.4% |
| Non-GAAP adjustments: |  |  |  |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net realized and unrealized losses on fixed maturity investments and funds held - directly managed / Net unrealized gains on fixed maturity investments and funds held - directly managed <sup>(2)</sup> | 1181 | (89) |  | 210 | (560) |  | (306) | (277) |  |
| &nbsp;&nbsp;&nbsp;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 <sup>(3)</sup> | (200) | (107) |  | (75) | (33) |  | 119 | (130) |  |
| &nbsp;&nbsp;&nbsp;Amortization of fair value adjustments / Fair value adjustments | (18) | (106) |  | 16 | (128) |  | 27 | (152) |  |
| &nbsp;&nbsp;&nbsp;Net gain on purchase and sales of subsidiaries |  |  |  | (73) |  |  | (3) |  |  |
| &nbsp;&nbsp;&nbsp;Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations |  |  |  |  |  |  | (16) | (266) |  |
| &nbsp;&nbsp;&nbsp;Tax effects of adjustments <sup>(4)</sup> | (7) |  |  | (21) |  |  | 23 |  |  |
| &nbsp;&nbsp;&nbsp;Adjustments attributable to noncontrolling interests <sup>(5)</sup> | (111) |  |  | 6 |  |  | 13 | 109 |  |
| **Adjusted operating (loss) income/Adjusted opening equity/Adjusted ROE\*** | $(61) | $5511 | (1.1)% | $565 | $5605 | 10.1% | $1580 | $3774 | 41.9% |

---

<sup>(1)</sup> 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.

<sup>(2)</sup> 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.

<sup>(3)</sup> Comprises the discount rate and risk margin components.

<sup>(4)</sup> 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.

<sup>(5)</sup> 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 measure.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;15

------

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

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **Year Ended** | **As of** | **As of** | **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)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| **PPD/net loss reserves/RLE** | $756 | $12011 | $11926 | $11969 | 6.3% |
| Non-GAAP Adjustments: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Assumed Life | (55) |  | (181) | (91) |  |
| &nbsp;&nbsp;&nbsp;Legacy Underwriting | 3 | (135) | (153) | (144) |  |
| &nbsp;&nbsp;&nbsp;Net loss reserves - current period |  | (45) |  | (23) |  |
| &nbsp;&nbsp;&nbsp;Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies | (18) | 124 | 106 | 115 |  |
| &nbsp;&nbsp;Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option <sup>(1)</sup> | (200) | 294 | 107 | 201 |  |
| &nbsp;&nbsp;&nbsp;Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities | 2 | 572 | 573 | 573 |  |
| &nbsp;&nbsp;&nbsp;Increase (reduction) in estimated future expenses - Defendant A&E | 1 | 35 | 37 | 36 |  |
| **Adjusted PPD/Adjusted net loss reserves/Adjusted RLE\*** | $489 | $12856 | $12415 | $12636 | 3.9% |

---

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **Year Ended** | **As of** | **As of** | **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)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| **PPD/net loss reserves/RLE** | $403 | $11926 | $8763 | $10344 | 3.9% |
| Non-GAAP Adjustments: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Assumed Life |  | (179) |  | (90) |  |
| &nbsp;&nbsp;&nbsp;Legacy Underwriting | (6) | (140) | (955) | (548) |  |
| &nbsp;&nbsp;&nbsp;Net loss reserves - current period |  | (143) |  | (72) |  |
| &nbsp;&nbsp;&nbsp;Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies | 16 | 106 | 128 | 117 |  |
| &nbsp;&nbsp;Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option <sup>(1)</sup> | (75) | 107 | 33 | 70 |  |
| &nbsp;&nbsp;&nbsp;Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities | 38 | 573 | 615 | 594 |  |
| &nbsp;&nbsp;&nbsp;Increase (reduction) in estimated future expenses - Defendant A&E | 5 | 37 | 43 | 40 |  |
| **Adjusted PPD/Adjusted net loss reserves/Adjusted RLE\*** | $381 | $12287 | $8627 | $10455 | 3.6% |

---

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;16

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---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **Year Ended** | **As of** | **As of** | **As of** | **Year Ended** |
| | **December 31, 2020** | **December 31, 2020** | **December 31, 2019** | **December 31, 2020** | **December 31, 2020** |
| | **PPD** | **Net loss reserves** | **Net loss reserves** | **Average net loss reserves** | **RLE %** |
| | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** | **(in millions of U.S. dollars)** |
| **PPD/net loss reserves/RLE** | $32 | $8763 | $7941 | $8352 | 0.4% |
| Non-GAAP Adjustments: |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Legacy Underwriting | (4) | (702) | (1184) | (943) |  |
| &nbsp;&nbsp;&nbsp;Net loss reserves - current period |  | (273) |  | (137) |  |
| &nbsp;&nbsp;&nbsp;Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies | 28 | 128 | 152 | 140 |  |
| &nbsp;&nbsp;Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option <sup>(1)</sup> | 119 | 33 | 130 | 82 |  |
| &nbsp;&nbsp;&nbsp;Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities | 103 | 615 | 561 | 588 |  |
| &nbsp;&nbsp;&nbsp;Increase (reduction) in estimated future expenses - Defendant A&E | 9 | 43 | 52 | 48 |  |
| **Adjusted PPD/Adjusted net loss reserves/Adjusted RLE\*** | $287 | $8607 | $7652 | $8129 | 3.5% |

---

<sup>(1)</sup> Comprises the discount rate and risk margin components.

\*Non-GAAP measure.

**Enstar** Group Limited \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;17

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

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | **For the Three Months Ended December 31,** | **For the Three Months Ended December 31,** | **For the Year Ended<br>December 31,** | **For the Year Ended<br>December 31,** | **For the Year Ended<br>December 31,** |
| | **2022** | **2021** | **2022** | **2021** | **2020** |
| **Investment results** |  |  |  |  |  |
| Net investment income | $153 | $81 | $455 | $312 | $303 |
| Net realized (losses) gains | (24) | (62) | (135) | (61) | 19 |
| Net unrealized (losses) gains | 39 | 68 | (1479) | 178 | 1623 |
| Earnings (losses) from equity method investments | (86) | (8) | (74) | 93 | 239 |
| Other comprehensive income: |  |  |  |  |  |
| Unrealized (losses) gains on fixed income securities, AFS, net of reclassification adjustments excluding foreign exchange | 87 | (26) | (570) | (100) | 70 |
| **TIR ($)** | $169 | $53 | $(1803) | $422 | $2254 |
| Non-GAAP adjustments: |  |  |  |  |  |
| Net realized and unrealized losses (gains) on fixed maturity investments and funds held-directly managed | 20 | 27 | 1181 | 210 | (306) |
| Unrealized (losses) gains on fixed income securities, AFS, net of reclassification adjustments excluding foreign exchange | (87) | 26 | 570 | 100 | (70) |
| **Adjusted TIR ($)\*** | $102 | $106 | $(52) | $732 | $1878 |
| **Total investments** | 14628 | 17276 | 14628 | 17276 | 15257 |
| Cash and cash equivalents, including restricted cash and cash equivalents | 1330 | 2092 | 1330 | 2092 | 1373 |
| Funds held by reinsured companies | 3582 | 2340 | 3582 | 2340 | 636 |
| **Total investable assets** | $19540 | $21708 | $19540 | $21708 | $17266 |
| Average aggregate invested assets, at fair value <sup>(1)</sup> | $19503 | $21569 | $20079 | $20840 | $15443 |
| **Annualized TIR %** <sup>(2)</sup> | 3.5% | 1.0% | (9.0)% | 2.0% | 14.6% |
| 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 | 1827 | (89) | 1827 | (89) | (560) |
| **Adjusted investable assets\*** | $21367 | $21619 | $21367 | $21619 | $16706 |
| Adjusted average aggregate invested assets, at fair value <sup>(3)</sup> | $21380 | $21438 | $21165 | $20561 | $15153 |
| **Annualized adjusted TIR %\*** <sup>(4)</sup> | 1.9% | 2.0% | (0.2)% | 3.6% | 12.4% |

---

<sup>(1)</sup> This amount is a two period average of the total investable assets for the three months ended December 31, 2022 and 2021, respectively, and a five period average for the years ended December 31, 2022, 2021 and 2020, respectively, as presented above, and is comprised of amounts disclosed in our quarterly and annual U.S. GAAP consolidated financial statements.

<sup>(2)</sup> Annualized TIR % is calculated by dividing the annualized TIR ($) by average aggregate invested assets, at fair value.

<sup>(3)</sup> This amount is a two period average of the total investable assets for the three months ended December 31, 2022 and 2021, respectively, and a five period average for the years ended December 31, 2022, 2021 and 2020, respectively, as presented above.

<sup>(4)</sup> 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 \| 2022 Press Release &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;18

## Exhibit 99.2

![](a2022q4-investorfinancia001.jpg)

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement December 31, 2022

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![](a2022q4-investorfinancia002.jpg)

\| 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 Adjusted 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

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\| enstargroup.com 3 Explanatory Notes About Enstar Enstar is a NASDAQ-listed leading global (re)insurance group that offers innovative capital release solutions through its network of group companies in Bermuda, the United States, the United Kingdom, Continental Europe, Australia, and other international locations. A market leader in completing legacy acquisitions, Enstar has acquired over 110 companies and portfolios since its formation in 2001. For further information about Enstar, see www.enstargroup.com. Basis of Presentation In this Investor Financial Supplement, the terms "we," "us," "our," "Enstar," or "the Company" refer to Enstar Group Limited and its consolidated subsidiaries. All information contained herein is unaudited. Unless otherwise noted, amounts are in millions of U.S. Dollars, except for share and per share amounts. 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. Change in Accounting Principle Effective for 2022, we changed our accounting principle for the treatment of DCA amortization and retrospectively applied this change to all prior period information. As of January 1, 2020, the cumulative effect of this change resulted in a $158 million increase to retained earnings. We regard DCA as an adjustment to the liabilities that we acquire and record at book value. As a result, DCA reflects the time value of money difference between the premium received and liabilities recorded. In addition, we no longer adjust DCA amortization as if any change in the amount of related liabilities were known on inception, and we have separated DCA amortization from our measures of run-off liability earnings ("RLE") and RLE % as we now view DCA as a separate overall cost of the acquisition of the contract. For additional information, please refer to Note 2 and Note 9 of our consolidated financial statements included within Item 8 of our Annual Report on Form 10-K for the year ended December 31, 2022. GAAP Financial Measures We amended our calculation of TIR to include the unrealized gains (losses) on our AFS securities, net of reclassification adjustments and excluding foreign exchange, included within other comprehensive income ("OCI"). We believe this represents a better measure of "total" investment return, and eliminates the discrepancy between the numerator and denominator, whereby the fair value of AFS securities includes any unrealized gains (losses) in AOCI. 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 income securities 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 investment 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.

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4 Explanatory Notes (continued) Non-GAAP Financial Measures (continued) We have changed our non-GAAP measures in 2022 as follows: • The opening GAAP balances of our 2021 and 2020 Adjusted BVPS\*, Adjusted ROE\* and Adjusted RLE\* measures have been retrospectively adjusted for a change in accounting principle, as described above. • We no longer remove ULAE from our Adjusted RLE and RLE % calculations as our estimate of future claims handling costs is connected to our claims settlement strategies and outcomes and the RLE measures now reflect the direct and indirect performance of the management of our liabilities. Presentation of GAAP and Non-GAAP Measures We complete most of our annual loss reserve studies in the fourth quarter of each year and, as a result, tend to record the largest movements, both favorable and adverse, to net incurred losses and LAE in this period. As such, we have not included our quarter to date calculation of Annualized RLE % and Annualized Adjusted RLE %\*, as annualizing the quarter to date measures would misrepresent our expected annual results. 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 ("ETF") where the underlying exposure of the ETF is an investment in investment grade fixed income securities. U.S. GAAP requires that the investment be classified as "Equities". 2. Enstar has certain private equity funds that are collectively held in a limited partnership. U.S. GAAP requires that the investment be classified as "Private equity funds" within "Other Investments". 3. Enstar has certain privately held equities that are required to be classified as "Equities" under U.S. GAAP. 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 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. \* Non-GAAP financial measure.

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\| enstargroup.com 5 Three Months Ended Year Ended December 31, 2022 December 31, 2021 December 31, 2022 December 31, 2021 Key Earnings Metrics ROE 5.9 % 2.1 % (15.6) % 7.9 % Adjusted ROE (1) 4.2 % 2.5 % (1.1) % 10.1 % Basic net earnings (loss) per share $13.34 $6.74 $(52.65) $25.33 Diluted net earnings (loss) per share $13.26 $6.66 $(52.65) $24.94 Key Run-off Metrics Average net loss reserves $11,969 $10,344 Run-off liability earnings ("RLE") 6.3 % 3.9 % Average adjusted net loss reserves (1) $12,636 $10,455 Adjusted RLE (1) 3.9 % 3.6 % Key Investment Return Metrics Average aggregate invested assets $19,503 $21,569 $20,079 $20,840 Annualized Total investment return ("TIR") 3.5 % 1.0 % (9.0) % 2.0 % Investment book yield 3.33 % 1.60 % 2.47 % 1.84 % (Losses) earnings from equity method investments $(86) $(8) $(74) $93 Adjusted average aggregate invested assets (1) $21,380 $21,438 $21,165 $20,561 Annualized adjusted TIR (1) 1.9 % 2.0 % (0.2) % 3.6 % Key Shareholder Metrics Ordinary shareholders' equity $4,191 $5,813 Total Enstar shareholders' equity $4,701 $6,323 Book value per ordinary share ("BVPS") $246.20 $329.20 Adjusted BVPS (1) $243.09 $323.43 Change in adjusted BVPS (24.8) % 12.1 % Ordinary shares repurchased: Shares — 167,617 697,580 4,010,695 Cost $— $40 $163 $942 Average price per share $— $241.13 $233.92 $234.82 Total ordinary shares outstanding 17,022,420 17,657,944 Adjusted ordinary shares outstanding 17,240,591 17,973,149 Key Balance Sheet Metrics Total assets $22,154 $24,656 Debt obligations $1,829 $1,691 Total liabilities $17,189 $17,924 Total investable assets to ordinary shareholders' equity 4.66x 3.73x Total net loss reserves to ordinary shareholders' equity 2.87x 2.05x Debt to total capitalization attributable to Enstar 28.0 % 21.1 % 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.

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\| enstargroup.com 6 Year Ended December 31, 2022 December 31, 2021 December 31, 2020 December 31, 2019 December 31, 2018 (2) Key Earnings Metrics Return on equity (15.6) % 7.9 % 38.4 % 25.5 % (5.0) % Adjusted return on equity (1) (1.1) % 10.1 % 41.9 % 18.8 % 2.4 % Key Run-off Metrics Average net loss reserves $11,969 $10,344 $8,352 $7,641 $6,435 Run-off liability earnings 6.3 % 3.9 % 0.4 % 0.1 % 3.5 % Average adjusted net loss reserves (1) $12,636 $10,455 $8,129 $7,160 $5,847 Adjusted run-off liability earnings (1) 3.9 % 3.6 % 3.5 % 4.0 % 6.4 % Key Investment Return Metrics Average investable assets $20,079 $20,840 $15,443 $13,758 $10,322 Total investment return (9.0) % 2.0 % 14.6 % 10.0 % (1.0) % Investment book yield 2.47 % 1.84 % 2.53 % 2.80 % 2.50 % (Losses) earnings from equity method investments $(74) $93 $239 $56 $42 Average adjusted investable assets (1) $21,165 $20,561 $15,153 $13,646 $10,393 Adjusted total investment return (1) (0.2) % 3.6 % 12.4 % 6.3 % 1.3 % Key Shareholder Metrics Ordinary shareholders' equity $4,191 $5,813 $6,326 $4,490 $3,546 Total Enstar shareholders' equity $4,701 $6,323 $6,836 $5,000 $4,056 Basic book value per ordinary share $246.20 $329.20 $293.97 $208.73 $165.23 Adjusted book value per ordinary share (1) $243.09 $323.43 $288.56 $205.11 $162.98 Change in adjusted book value per ordinary share (24.8) % 12.1 % 40.7 % 25.9 % (2.5) % Ordinary shares repurchased: Shares 697,580 4,010,695 178,280 — — Cost $163 $942 $26 $— $— Average price per share $233.92 $234.82 $145.87 $— $— Total ordinary shares outstanding 17,022,420 17,657,944 21,519,602 21,511,505 21,459,997 Adjusted ordinary shares outstanding 17,240,591 17,973,149 21,993,598 21,989,971 21,881,063 Key Balance Sheet Metrics Total assets $22,154 $24,656 $21,789 $19,984 $16,710 Debt obligations $1,829 $1,691 $1,373 $1,191 $862 Total liabilities $17,189 $17,924 $14,574 $14,531 $12,184 Total investable assets to ordinary shareholders' equity 4.66x 3.73x 2.73x 3.13x 3.54x Total net loss reserves to ordinary shareholders' equity 2.87x 2.05x 1.39x 1.77x 2.07x Debt to total capitalization attributable to Enstar 28.0 % 21.1 % 16.7 % 19.2 % 17.5 % 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 2017 and 2018 balance sheets have not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification.

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\| enstargroup.com 7 Book Value Per Share & Return on Equity - Five Years Growth in Book Value Per Ordinary Share and Adjusted Book Value Per Ordinary Share\* Annual % Change $165.23 $208.73 $293.97 $329.20 $246.20 $162.98 $205.11 $288.56 $323.43 $243.09 Book Value Per Ordinary Share Adjusted Book Value Per Ordinary Share\* 2018 2019 2020 2021 2022 $0 $50 $100 $150 $200 $250 $300 $350 Return on Equity and Adjusted Return on Equity\* (5.0)% 25.5% 38.4% 7.9% (15.6)% 2.4% 18.8% 41.9% 10.1% (1.1)% Return on Equity Adjusted Return on Equity\* 2018 2019 2020 2021 2022 26.3% 25.9% 40.8% 40.7% 12.0% 12.1% (25.2)% (24.8)% (2.7)% (2.5)% \* 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.

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\| enstargroup.com 8 Consolidated Results by Segment - Q4 2022 Three Months Ended December 31, 2022 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total INCOME Net premiums earned $13 $— $— $1 $— $14 Net investment income — — 151 2 — 153 Net realized losses — — (24) — — (24) Net unrealized gains — — 37 2 — 39 Other income (expense) 3 — — (3) 2 2 Total income 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 34 1 9 2 51 97 Total expenses (207) (25) 9 2 70 (151) EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 223 25 155 — (68) 335 Losses from equity method investments — — (86) — — (86) SEGMENT EARNINGS (LOSS) $223 $25 $69 $— (68) 249 Interest expense (18) (18) Net foreign exchange losses (12) (12) Income tax benefit 16 16 NET EARNINGS 235 Net loss attributable to noncontrolling interests 1 1 NET EARNINGS ATTRIBUTABLE TO ENSTAR 236 Dividends on preferred shares (9) (9) NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $(90) $227 (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.

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\| enstargroup.com 9 Consolidated Results by Segment - Q4 2021 Three Months Ended December 31, 2021 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total INCOME Net premiums earned $28 $5 $— $8 $— $41 Net investment income — — 80 1 — 81 Net realized losses — — (62) — — (62) Net unrealized gains (losses) — — 69 (1) — 68 Other income (expense) 25 — — (4) (6) 15 Net gain of purchase and sale of subsidiaries — — — — 11 11 Total income 53 5 87 4 5 154 EXPENSES Net incurred losses and loss adjustment expenses Current period 23 2 — 1 — 26 Prior period (154) — — (1) (4) (159) Total net incurred losses and loss adjustment expenses (131) 2 — — (4) (133) Policyholder benefit expenses — (4) — — 1 (3) Amortization of net deferred charge assets — — — — 17 17 Acquisition costs 7 — — — — 7 General and administrative expenses 49 1 13 4 31 98 Total expenses (75) (1) 13 4 45 (14) EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 128 6 74 — (40) 168 Losses from equity method investments — — (8) — — (8) SEGMENT EARNINGS (LOSS) $128 $6 $66 $— (40) 160 Interest expense (18) (18) Net foreign exchange gains 3 3 Income tax expense (14) (14) NET EARNINGS 131 Net earnings attributable to noncontrolling interests (2) (2) NET EARNINGS ATTRIBUTABLE TO ENSTAR 129 Dividends on preferred shares (9) (9) NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $(80) $120 (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.

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\| enstargroup.com 10 Consolidated Results by Segment - 2022 Year Ended December 31, 2022 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total INCOME Net premiums earned $40 $17 $— $9 $— $66 Net investment income — — 445 10 — 455 Net realized losses — — (135) — — (135) Net unrealized losses — — (1,469) (10) — (1,479) Other income 22 — — 1 12 35 Total income (loss) 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) EARNINGS (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.

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\| enstargroup.com 11 Consolidated Results by Segment - 2021 Year Ended December 31, 2021 Run-off Assumed Life Investments Legacy Underwriting Corporate and other (1) Total INCOME Net premiums earned $182 $5 $— $58 $— $245 Net investment income — — 309 3 — 312 Net realized gains — — (61) — — (61) Net unrealized gains (losses) — — 181 (3) — 178 Other income (expense) 73 — — (15) (16) 42 Net gain on purchase and sale of subsidiaries — — — — 73 73 Total income 255 5 429 43 57 789 EXPENSES Net incurred losses and loss adjustment expenses Current period 144 2 — 26 — 172 Prior period (338) — — (6) (59) (403) Total net incurred losses and loss adjustment expenses (194) 2 — 20 (59) (231) Policyholder benefit expenses — (4) — — 1 (3) Amortization of net deferred charge assets — — — — 55 55 Acquisition costs 44 — — 13 — 57 General and administrative expenses 188 1 37 10 131 367 Total expenses 38 (1) 37 43 128 245 EARNINGS (LOSS) BEFORE INTEREST EXPENSE, FOREIGN EXCHANGE AND INCOME TAXES 217 6 392 — (71) 544 Earnings from equity method investments — — 93 — — 93 SEGMENT INCOME (LOSS) $217 $6 $485 $— (71) 637 Interest expense (69) (69) Net foreign exchange gains 12 12 Income tax expense (27) (27) NET EARNINGS 553 Net earnings attributable to noncontrolling interests (15) (15) NET EARNINGS ATTRIBUTABLE TO ENSTAR 538 Dividends on preferred shares (36) (36) NET (LOSS) EARNINGS ATTRIBUTABLE TO ENSTAR ORDINARY SHAREHOLDERS $(206) $502 (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.

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\| enstargroup.com 12 Prior Period Development ("PPD") by Acquisition year PPD in Year Ended December 31, Acquisition Year 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (unaudited) 2012 and prior $259 $259 $239 $128 $90 $61 $72 $44 $34 $15 2013 (2) 30 43 32 43 46 14 16 9 (1) 2014(1) 30 18 18 34 (112) (110) 1 25 30 2015 87 301 42 79 28 20 21 12 2016 9 (34) 18 9 21 10 14 2017 84 98 (84) (50) 89 183 2018 33 42 18 45 58 2019 33 33 47 59 2020 (71) (27) (120) 2021 150 435 2022 71 $257 $319 $387 $488 $259 $223 $4 $32 $403 $756 Acquisition Year Cumulative PPD in Year Ended December 31, 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (unaudited) 2012 and prior $259 $518 $757 $885 $975 $1,036 $1,108 $1,152 $1,186 $1,201 2013 (2) 28 71 103 146 192 206 222 231 230 2014(1) 30 48 66 100 (12) (122) (121) (96) (66) 2015 87 388 430 509 537 557 578 590 2016 9 (25) (7) 2 23 33 47 2017 84 182 98 48 137 320 2018 33 75 93 138 196 2019 33 66 113 172 2020 (71) (98) (218) 2021 150 585 2022 71 (1) The 2014 acquisition year includes losses relating to our StarStone business when this business was actively managed within our Legacy Underwriting segment.

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\| 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 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (Unaudited) 2012 and prior(1) $2,738 $— $2,738 $2,479 $2,220 $1,981 $1,853 $1,763 $1,702 $1,630 $1,586 $1,552 $1,537 2013 854 — 854 856 826 783 751 708 662 648 632 623 624 2014 1,057 — 1,057 1,027 1,009 991 957 1,069 1,179 1,178 1,153 1,123 2015 1,756 — 1,756 1,669 1,368 1,326 1,247 1,219 1,199 1,178 1,166 2016 1,357 — 1,357 1,348 1,382 1,364 1,355 1,334 1,324 1,310 2017 1,536 — 1,536 1,452 1,354 1,438 1,488 1,399 1,216 2018 2,757 — 2,757 2,724 2,682 2,664 2,619 2,561 2019 1,817 — 1,817 1,784 1,751 1,704 1,645 2020(2) 2,191 (782) 1,409 1,480 1,507 1,627 2021(3) 3,710 840 4,550 4,400 3,965 2022(2) 2,649 782 3,431 3,360 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) 2012 and prior 100 % 91 % 81 % 72 % 68 % 64 % 62 % 60 % 58 % 57 % 56 % 2013 100 % 97 % 92 % 88 % 83 % 78 % 76 % 74 % 73 % 73 % 2014(4) 97 % 95 % 94 % 91 % 101 % 112 % 111 % 109 % 106 % 2015 95 % 78 % 76 % 71 % 69 % 68 % 67 % 66 % 2016 99 % 102 % 101 % 100 % 98 % 98 % 97 % 2017 95 % 88 % 94 % 97 % 91 % 79 % 2018 99 % 97 % 97 % 95 % 93 % 2019 98 % 96 % 94 % 91 % 2020 105 % 107 % 115 % 2021 97 % 87 % 2022 98 % (1) For the 2012 and prior acquisition years, the net reserves shown are as at December 31, 2012, and are not the net reserves assumed and acquired. (2) $782m 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.

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\| enstargroup.com 14 Adjusted PPD by Acquisition Year\* Adjusted PPD\* in Year Ended December 31, Acquisition Year 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (Unaudited) 2012 and prior $293 $281 $254 $152 $104 $78 $86 $51 $39 $27 2013 (30) 10 21 19 22 30 6 9 3 2 2014 2 (37) 1 1 8 5 3 30 15 2015 92 306 45 81 30 21 22 13 2016 9 (37) 41 16 36 8 22 2017 114 87 — 39 34 30 2018 50 109 69 38 19 2019 33 130 92 54 2020 (71) (27) (120) 2021 142 356 2022 71 $263 $293 $330 $487 $249 $375 $285 $287 $381 $489 Acquisition Year Cumulative Adjusted PPD\* in Year Ended December 31, 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (Unaudited) 2012 and prior $293 $574 $828 $980 $1,084 $1,162 $1,248 $1,299 $1,338 $1,365 2013 (30) (20) 1 20 42 72 78 87 90 92 2014 2 (35) (34) (33) (25) (20) (17) 13 28 2015 92 398 443 524 554 575 597 610 2016 9 (28) 13 29 65 73 95 2017 114 201 201 240 274 304 2018 50 159 228 266 285 2019 33 163 255 309 2020 (71) (98) (218) 2021 142 498 2022 71 \* 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.

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\| 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 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) (Unaudited) 2012 and prior(1) $2,950 $— $2,950 $2,657 $2,376 $2,122 $1,970 $1,866 $1,788 $1,702 $1,651 $1,612 $1,585 2013 626 — 626 656 646 625 606 584 554 548 539 536 534 2014 411 — 411 409 446 445 444 436 431 428 398 383 2015 1,782 — 1,782 1,690 1,384 1,339 1,258 1,228 1,207 1,185 1,172 2016 1,495 — 1,495 1,486 1,523 1,482 1,466 1,430 1,422 1,400 2017 1,719 — 1,719 1,605 1,518 1,518 1,479 1,445 1,415 2018 2,921 — 2,921 2,871 2,762 2,693 2,655 2,636 2019 2,340 — 2,340 2,307 2,177 2,085 2,031 2020(2) 2,205 (782) 1,423 1,494 1,521 1,641 2021(3) 3,709 1,611 5,320 5,178 4,822 2022(2) 2,649 782 3,431 3,360 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) 2012 and prior 100 % 90 % 81 % 72 % 67 % 63 % 61 % 58 % 56 % 55 % 54 % 2013 105 % 103 % 100 % 97 % 93 % 88 % 88 % 86 % 86 % 85 % 2014 100 % 109 % 108 % 108 % 106 % 105 % 104 % 97 % 93 % 2015 95 % 78 % 75 % 71 % 69 % 68 % 66 % 66 % 2016 99 % 102 % 99 % 98 % 96 % 95 % 94 % 2017 93 % 88 % 88 % 86 % 84 % 82 % 2018 98 % 95 % 92 % 91 % 90 % 2019 99 % 93 % 89 % 87 % 2020 105 % 107 % 115 % 2021 97 % 91 % 2022 98 % (1) For the 2012 and prior acquisition year, the adjusted net reserves shown are as at December 31, 2012 and are not the adjusted net reserves assumed and acquired. (2) $782m 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.

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\| enstargroup.com 16 Capital Position & Credit Ratings Credit ratings (1) Standard and Poor's Fitch Ratings Long-term issuer BBB (Outlook: Positive) BBB+ (Outlook: Stable) 2029 Senior Notes BBB BBB 2031 Senior Notes BBB- BBB 2040 and 2042 Junior Subordinated Notes BB+ BBB- Series D and E Preferred Shares BB+ BBB- (1) Credit ratings are provided by third parties, Standard & Poor's and Fitch Ratings, and are subject to certain limitations and disclaimers. For information on these ratings, refer to the rating agencies' websites and other publications. Total Capitalization $6,794 $8,423 $4,191 $5,813 $510 $510 $264 $409 $1,829 $1,691 26.9% 20.1% 34.4% 26.1% 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 2022 2021 Total Capitalization Attributable to Enstar $6,530 $8,014 $4,191 $5,813 $510 $510 $1,829 $1,691 28.0% 21.1% 35.8% 27.5% 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 2022 2021

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17 Non-GAAP Measures Non-GAAP Measure Definition Purpose of Non-GAAP Measure over GAAP Measure Adjusted book value per ordinary share Total Enstar ordinary shareholders' equity Divided by Number of ordinary shares outstanding, adjusted for: -the ultimate effect of any dilutive securities on the number of ordinary shares outstanding Increases the number of ordinary shares to reflect 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 maturity investments 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 income securities 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 maturity investments and funds held- directly managed, -change in fair value of insurance contracts for which we have elected the fair value option (1), -amortization of fair value adjustments, -net gain/loss on purchase and sales of subsidiaries (if any), -net earnings from discontinued operations (if any), -tax effects of adjustments, 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 maturity investments and funds held-directly managed, -fair value of insurance contracts for which we have elected the fair value option (1), -fair value adjustments, and -net assets of held for sale or disposed subsidiaries classified as discontinued operations (if any) Adjusted total investment return (%) Adjusted total investment return (dollars) recognized in earnings for the applicable period divided by period average adjusted total investable assets. Provides a key measure of the return generated on the capital held in the business and is reflective of our investment strategy. Provides a consistent measure of investment returns as a percentage of all assets generating investment returns. We adjust our investment returns to eliminate the impact of the change in fair value of fixed income securities (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 maturity investments and funds held- directly managed; and -unrealized (gains) losses on fixed income securities, 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 income securities, AFS included within AOCI -net unrealized (gains) losses on fixed income securities, trading (1) Comprises the discount rate and risk margin components.

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\| 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: • The results of our Legacy Underwriting segment have been economically transferred to a third party primarily through use of reinsurance and a Capacity Lease Agreement(2); as such, the results are 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 exposure to active property catastrophe business; as this business is not in run-off, the results are 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(3): -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(3): -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) As described in Note 5 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2022. (3) Effective for 2022, we are no longer excluding ULAE as it relates to our losses and LAE liabilities and are now including estimated future expenses as it relates to our defendant A&E liabilities in the calculation of Adjusted RLE\*, as these provisions are related to our insurance liabilities and contribute to our claims management performance. The comparative periods in 2021 and 2020 have been adjusted accordingly.

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\| enstargroup.com 19 Reconciliation to Adjusted Book Value Per Share For the Year Ended December 31, 2022 2021 2020 Equity (1) Ordinary Shares Per Share Amount 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 $4,191 17,022,420 $246.20 $5,813 17,657,944 $329.20 $6,326 21,519,602 $293.97 Non-GAAP adjustments: Share-based compensation plans — 218,171 — 315,205 — 298,095 Warrants — — — — 20 175,901 Adjusted book value per ordinary share\* $4,191 17,240,591 $243.09 $5,813 17,973,149 $323.43 $6,346 21,993,598 $288.56 For the Year Ended December 31, 2019 2018 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 $4,490 21,511,505 $208.73 $3,546 21,459,997 $165.23 Non-GAAP adjustments: Share-based compensation plans — 302,565 — 245,165 Warrants 20 175,901 20 175,901 Adjusted book value per ordinary share\* $4,510 21,989,971 $205.11 $3,566 21,881,063 $162.98 (1) Equity comprises Enstar ordinary shareholders' equity, which is calculated as Enstar shareholders' equity less preferred shares ($510 million as of December 31, 2022, 2021, 2020, 2019, and 2018, respectively), prior to any non-GAAP adjustments. \* Non-GAAP financial measure.

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\| enstargroup.com 20 Reconciliation to Adjusted Return on Equity - Q4 2022 and Q4 2021 Three Months Ended December 31, 2022 2021 Net (loss) earnings (1) Opening equity (1) (Adj) ROE Net (loss) earnings (1) Opening equity (1) (Adj) ROE Net (loss) earnings/Opening equity/ROE (1) $227 $3,866 5.9 % $120 $5,749 2.1 % Non-GAAP adjustments: Net realized and unrealized losses (gains) on fixed maturity investments and funds held - directly managed / Net unrealized losses (gains) on fixed maturity investments and funds held - directly managed (2) 20 1,926 27 (176) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) 28 (305) (6) (100) Amortization of fair value adjustments / Fair value adjustments (29) (95) 3 (109) Net gain on purchase and sales of subsidiaries — — (11) — Tax effects of adjustments (4) (1) — (3) — Adjustments attributable to noncontrolling interests (5) (21) — 2 — Adjusted operating (loss) income/Adjusted opening equity/Adjusted ROE\* $224 $5,392 4.2 % $132 $5,364 2.5 % (1) Net (loss) earnings comprises net (loss) earnings attributable to Enstar ordinary shareholders, prior to any non-GAAP adjustments. Opening equity comprises Enstar ordinary shareholders' equity, which is calculated as opening Enstar shareholders' equity less preferred shares ($510 million), prior to any non-GAAP adjustments. (2) Represents the net realized and unrealized losses (gains) related to fixed maturity securities. Our fixed maturity securities are held directly on our balance sheet and also within the "Funds held - directly managed" balance. (3) Comprises the discount rate and risk margin components. (4) Represents an aggregation of the tax expense or benefit associated with the specific country to which the pre-tax adjustment relates, calculated at the applicable jurisdictional tax rate. (5) Represents the impact of the adjustments on the net earnings (loss) attributable to noncontrolling interests associated with the specific subsidiaries to which the adjustments relate. \* Non-GAAP financial measure. (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 as of September 30, 2022 and 2021), 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.

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\| enstargroup.com 21 Reconciliation to Adjusted Return on Equity - 2022, 2021 and 2020 (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 as of December 31, 2021, 2020 and 2019), 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. For the Year Ended December 31, 2022 2021 2020 Net (loss) earnings (1) Opening Equity (1) (Adj) ROE Net earnings (1) Opening Equity (1) (Adj) ROE Net earnings (1) Opening Equity (1) (Adj) ROE Net (loss) earnings/Opening equity/ROE (1) $(906) $5,813 (15.6) % $502 $6,326 7.9 % $1,723 $4,490 38.4 % Non-GAAP adjustments: Net realized and unrealized losses on fixed maturity investments and funds held - directly managed / Net unrealized gains on fixed maturity investments and funds held - directly managed (2) 1,181 (89) 210 (560) (306) (277) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) (200) (107) (75) (33) 119 (130) Amortization of fair value adjustments / Fair value adjustments (18) (106) 16 (128) 27 (152) Net gain on purchase and sales of subsidiaries — — (73) — (3) — Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations — — — — (16) (266) Tax effects of adjustments (4) (7) — (21) — 23 — Adjustments attributable to noncontrolling interests (5) (111) — 6 — 13 109 Adjusted net (loss) earnings/Adjusted opening equity/Adjusted ROE\* $(61) $5,511 (1.1) % $565 $5,605 10.1 % $1,580 $3,774 41.9 %

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\| enstargroup.com 22 Reconciliation to Adjusted Return on Equity - 2019 and 2018 For the Year Ended December 31, 2019 2018 Net earnings (1) Opening Equity (1) (6) (Adj) ROE Net (loss) earnings (1) Opening Equity (1) (6) (Adj) ROE (in millions of U.S. dollars) Net (loss) earnings/Opening equity/ROE (1) $906 $3,546 25.5 % $(166) $3,295 (5.0) % Non-GAAP adjustments: Net realized and unrealized losses (gains) on fixed maturity investments and funds held - directly managed / Unrealized (losses) gains on fixed maturity investments and funds held - directly managed (2) (516) 227 237 (101) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) 117 (244) 7 (183) Amortization of fair value adjustments / Fair value adjustments 51 (199) 7 (104) Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations (7) (210) (1) (157) Tax effects of adjustments (4) 36 — (18) — Adjustments attributable to noncontrolling interests (5) 15 86 3 65 Adjusted net (loss) earnings/Adjusted opening equity/Adjusted ROE\* $602 $3,206 18.8 % $69 $2,815 2.4 % (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 as of December 31, 2018), prior to any non-GAAP adjustments. (2) Represents the net realized and unrealized gains and losses 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. (6) The 2017 and 2018 balance sheets have not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. \* Non-GAAP financial measure.

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\| enstargroup.com 23 Reconciliation to Adjusted Run-off Liability Earnings - 2022 and 2021 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: Net loss reserves - 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 % (1) Comprises the discount rate and risk margin components. \* Non-GAAP financial 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: Net loss reserves - 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 36 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE\* $489 $12,856 $12,415 $12,636 3.9 %

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\| enstargroup.com 24 Reconciliation to Adjusted Run-off Liability Earnings - 2020 and 2019 Year Ended As of Year Ended December 31, 2020 December 31, 2020 December 31, 2019 December 31, 2020 December 31, 2020 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: Net loss reserves - 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 % Year Ended As of Year Ended December 31, 2019 December 31, 2019 December 31, 2018 December 31, 2019 December 31, 2019 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: Net loss reserves - 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.

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\| enstargroup.com 25 Reconciliation to Adjusted Run-off Liability Earnings - 2018 Year Ended As of Year Ended December 31, 2018 December 31, 2018 December 31, 2017 December 31, 2018 December 31, 2018 PPD Net loss reserves (2) Net loss reserves (2) Average net loss reserves (2) RLE % (in millions of U.S. dollars) PPD/Net loss reserves/RLE $223 $7,341 $5,528 $6,435 3.5 % Non-GAAP Adjustments: Net loss reserves - current period — (357) — (179) Legacy Underwriting 115 (818) (946) (882) Amortization of fair value adjustments / Net fair value adjustments associated with the acquisition of companies 7 199 103 151 Changes in fair value - fair value option / Net fair value adjustments for contracts for which we have elected the fair value option (1) 7 244 183 213 Change in estimate of net ultimate liabilities - defendant A&E / Net nominal defendant A&E liabilities 23 84 113 99 Reduction in estimated future expenses - defendant A&E / Estimated future expenses - defendant A&E — 20 — 10 Adjusted PPD/Adjusted net loss reserves/Adjusted RLE\* $375 $6,713 $4,981 $5,847 6.4 % (1) Comprises the discount rate and risk margin components. (2) The 2017 and 2018 balance sheets have not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. \* Non-GAAP financial measure.

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\| enstargroup.com 26 Reconciliation to Adjusted Total Investment Return For the Three Months Ended December 31, For the Year Ended December 31, 2022 2021 2022 2021 2020 2019 2018 Investment results Net investment income $153 $81 $455 $312 $303 $308 $262 Net realized (losses) gains (24) (62) (135) (61) 19 5 (1) Net unrealized gains (losses) 39 68 (1,479) 178 1,623 1,007 (407) Earnings (losses) from equity method investments (86) (8) (74) 93 239 56 42 Other comprehensive income: Unrealized gains (losses) on fixed income securities, AFS, net of reclassification adjustments excluding foreign exchange 87 (26) (570) (100) 70 (3) (2) TIR ($) $169 $53 $(1,803) $422 $2,254 $1,373 $(106) Non-GAAP adjustments: Net realized and unrealized losses (gains) on fixed maturity investments and funds held-directly managed 20 27 1,181 210 (306) (516) 237 Unrealized (losses) gains on fixed income securities, AFS, net of reclassification adjustments excluding foreign exchange (87) 26 570 100 (70) 3 2 Adjusted TIR ($)\* $102 $106 $(52) $732 $1,878 $860 $133 Total investments 14,628 17,276 14,628 17,276 15,257 12,620 11,242 Cash and cash equivalents, including restricted cash and cash equivalents 1,330 2,092 1,330 2,092 1,373 971 983 Funds held by reinsured companies 3,582 2,340 3,582 2,340 636 476 321 Total investable assets $19,540 $21,708 $19,540 $21,708 $17,266 $14,067 $12,546 Average aggregate invested assets, at fair value (1) $19,503 $21,569 $20,079 $20,840 $15,443 $13,758 $10,332 Annualized TIR % (2) 3.5 % 1.0 % (9.0) % 2.0 % 14.6 % 10.0 % (1.0) % 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 1,827 (89) 1,827 (89) (560) (275) 222 Adjusted investable assets\* $21,367 $21,619 $21,367 $21,619 $16,706 $13,792 $12,768 Adjusted average aggregate invested assets, at fair value (3) $21,380 $21,438 $21,165 $20,561 $15,153 $13,646 $10,393 Annualized adjusted TIR %\* (4) 1.9 % 2.0 % (0.2) % 3.6 % 12.4 % 6.3 % 1.3 % (1) This amount is a two period average of the total investable assets for the three months ended December 31, 2022 and 2021, respectively, and a five period average for the years ended December 31, 2022, 2021, 2020, 2019 and 2018, respectively, as presented above, and is comprised of amounts disclosed in our quarterly and annual U.S. GAAP consolidated financial statements. (2) Annualized TIR % is calculated by dividing the annualized TIR ($) by average aggregate invested assets, at fair value. (3) This amount is a two period average of the total investable assets for the three months ended December 31, 2022 and 2021, respectively, and a five period average for the years ended December 31, 2022, 2021, 2020, 2019 and 2018, 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.

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\| enstargroup.com 27 Reconciliation of PPD by Acquisition Year PPD in year ended December 31 Acquisition year 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) 2012 and prior PPD 259 259 239 128 90 61 72 44 34 15 FVA 34 22 15 24 14 17 14 7 5 12 2012 and prior Adjusted PPD 293 281 254 152 104 78 86 51 39 27 2013 PPD (2) 30 43 32 43 46 14 16 9 (1) Legacy — (19) (22) (13) (21) (14) (8) (7) (6) 3 FVA (28) (1) — — — (2) — — — — 2013 Adjusted PPD (30) 10 21 19 22 30 6 9 3 2 2014 PPD — 30 18 18 34 (112) (110) 1 25 30 Legacy — (11) (39) (14) (27) 127 115 3 8 (14) FVA — (17) (16) (3) (6) (7) — (1) (3) (1) 2014 Adjusted PPD — 2 (37) 1 1 8 5 3 30 15 2015 PPD — — 87 301 42 79 28 20 21 12 FVA — — 5 5 3 2 2 1 1 1 2015 Adjusted PPD — — 92 306 45 81 30 21 22 13 2016 PPD — — — 9 (34) 18 9 21 10 14 Defendant A&E — — — — — 23 4 13 (4) 7 Defendant A&E ULAE — — — — (3) — 3 2 2 1 2016 Adjusted PPD — — — 9 (37) 41 16 36 8 22 2017 PPD — — — — 84 98 (84) (50) 89 183 FVO — — — — 30 (11) 84 89 (55) (153) 2017 Adjusted PPD — — — — 114 87 — 39 34 30 2018 PPD — — — — — 33 42 18 45 58 Legacy — — — — — 2 (1) — — — FVO — — — — — 18 33 30 (20) (47) FVA — — — — — (3) 35 21 13 8 2018 Adjusted PPD — — — — — 50 109 69 38 19 2019 PPD — — — — — — 33 33 47 59 Defendant A&E — — — — — — — 90 42 (5) Defendant A&E ULAE — — — — — — — 7 3 — 2019 Adjusted PPD — — — — — — 33 130 92 54 \* Non-GAAP financial measure. Cumulative Adjusted PPD on page 14 is merely the sum of the relevant numbers in the table above.

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\| 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 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (in millions of U.S. dollars) 2020 PPD — — — — — — — (71) (27) (120) 2020 Adjusted PPD — — — — — — — (71) (27) (120) 2021 PPD — — — — — — — — 150 435 Legacy — — — — — — — — (8) 14 Assumed Life — — — — — — — — — (55) FVA — — — — — — — — — (38) 2021 Adjusted PPD — — — — — — — — 142 356 2022 PPD — — — — — — — — — 71 2022 Adjusted PPD — — — — — — — — — 71 All Acquisition Years PPD 257 319 387 488 259 223 4 32 403 756 Legacy — (30) (61) (27) (48) 115 106 (4) (6) 3 Assumed Life — — — — — — — — — (55) FVO — — — — 30 7 117 119 (75) (200) FVA 6 4 4 26 11 7 51 28 16 (18) Defendant A&E — — — — — 23 4 103 38 2 Defendant A&E ULAE — — — — (3) — 3 9 5 1 All Acquisition Years Adjusted PPD 263 293 330 487 249 375 285 287 381 489

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\| 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\* 2012 and prior reserves as at Dec 31 2012 (1) $2,738 $— $— $212 $— $— $— $2,950 $2,950 $— $2,950 2013 854 — (200) (28) — — — 626 626 — 626 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 (1) For the 2012 and prior acquisition years, the net reserves shown are as at December 31, 2012, 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) $782m 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.

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\| enstargroup.com 30 Investment Composition - 2022 Other Investments Equities Cash(2) 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 Short-term and fixed maturity investments, trading and AFS and funds held - directly managed $9,631 49.3 % Other assets included within funds held - directly managed 54 0.3 % 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 % — % 10 % — % — % 2 % — % 14 % — % — % 31 % 35 % 8 % — % Other investments Hedge funds (1) 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 % 24 % — % 25 % 11 % — % 14 % 8 % 1 % — % 2 % — % 1 % Equity method investments 397 2.0 % Total investments 14,628 74.9 % Cash and cash equivalents (including restricted cash) 1,330 6.8 % Funds held by reinsured companies 3,582 18.3 % Total investable assets $19,540 100.0 % (1) Infrastructure in fund format. (2(Cash and cash equivalents.

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\| enstargroup.com 31 Investment Composition - 2021 Other Investments Equities December 31, 2021 Hedge Funds Fixed income funds Equity funds Private equity funds CLO equities CLO equity funds Private credit funds Real estate debt fund Publicly traded equities Exchange- traded funds Privately held equities Short-term and fixed maturity investments, trading and AFS and funds held - directly managed $12,254 56.4 % Other assets included within funds held - directly managed 201 0.9 % Equities Publicly traded equities 281 1.3 % 281 Exchange-traded funds 1,342 6.2 % 969 373 Privately held equities 372 1.7 % 64 11 32 25 240 Total 1,995 9.2 % — % 52 % — % — % 2 % — % 1 % — % 14 % 19 % 12 % Other investments Hedge funds (1) 291 1.3 % 291 Fixed income funds 573 2.6 % 573 Equity funds 5 — % 5 Private equity funds 752 3.5 % 631 85 33 3 CLO equities 161 0.7 % 161 CLO equity funds 207 1.0 % 207 Private credit funds 275 1.3 % 275 Real estate debt fund 69 0.3 % 69 Total 2,333 10.7 % 12 % 25 % — % 27 % 16 % — % 16 % 4 % — % — % — % Equity method investments 493 2.3 % Total investments 17,276 79.6 % Cash and cash equivalents (including restricted cash) 2,092 9.6 % Funds held by reinsured companies 2,340 10.8 % Total investable assets $21,708 100.0 %

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## Exhibit 99.3

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Enstargroup.com Q4 2022 Review March 2023 Enstar Group Overview Realising Value

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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, risks relating to our active underwriting businesses, the performance of our investment portfolio and liquidity, and other factors detailed in our Annual Report on Form 10-K for the year ended December 31, 2022 and our other reports filed from time to time with the Securities and Exchange Commission ("SEC"). Any forward-looking statement you see or hear during the presentation reflects Enstar Group Limited's current views with respect to future events and is subject to these and other risks, uncertainties and assumptions. If any of these risks or uncertainties materialize, or if our underlying assumptions prove to be incorrect, actual results may vary significantly from what we projected. You are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the date on which they are made. The date of this presentation is listed on the cover page and Enstar does not undertake to update or keep it accurate after such date. 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 22 through 24 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

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enstargroup.com Deliver Capital Release and Risk Management Solutions to Insurance Market Industry founder and largest standalone provider Generate Positive Claims Outcomes "Enstar Effect" drives decades of Run-off Liability Earnings Growing Asset Base Using Origination Capabilities $19.5bn investable assets; 3.5x investment leverage1 What We Do 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, 2022, divided by opening equity as of December 31, 2021. 4Property of Enstar Group – Not for Distribution LEADING GLOBAL PROVIDER OF CAPITAL RELIEF SOLUTIONS Full suite of risk management solutions designed to create shareholder value

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enstargroup.com Run-off Focused Diversified Business Catalina Riverstone Int. DARAG Premia Compre Swiss Re NICO Longevity (>20yrs in Operation) Presence in Global Run-off Markets Experience in All Types of Run-off Transactions Deals Announced Since Inception1 117 ~31 ~34 ~60 ~9 ~56 N.A. N.A. Shareholders' Equity ($ Billions)2 4.8 ~1.4 ~1.3 Not Published ~0.6 ~0.25 ~12.7 ~2023 5Property of Enstar Group – Not for Distribution 1 These approximations are based upon publicly announced transactions. Includes two Riverstone transactions signed with Axis and Amlin which were announced after 30-Sept-2022. 2 As of latest company filings. As of 31-Dec-2022 for Enstar and Swiss Re. 30-Sept-2022 for Riverstone International and NICO. 31-Dec-2021 for Catalina, Premia, and Compre. 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

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enstargroup.com P&C Rates Continue to Strengthen for Primary Insurers Major Loss Events Including Recent CATs and COVID-19 Solvency II & Capital Efficiency Business Transfer Legislation Increased Consolidation Reserve Releases Declining Key Market Drivers Source: PwC Global Insurance Run-off Survey 2022. Inflation North America $464bn UK & Continental Europe $319bn Rest of World $177bn 6Property of Enstar Group – Not for Distribution SIGNIFICANT GROWING RUN-OFF MARKET $960bn opportunity, propelled by favorable global tailwinds

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enstargroup.com Total Assets$22.2bn Run-off Liability Earnings $756mNet Loss (results driven by unrealized losses) 1. Includes losses and loss adjustment expenses, future policyholder benefits, defendant A&E liabilities. 2. 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. $(906)m Q4: $227m Net Income Total Insurance Liabilities1$14.8bn Total Shareholders' Equity$4.8bn Core Fixed Income2'A+' 7Property of Enstar Group – Not for Distribution FINANCIAL HIGHLIGHTS Full Year 2022

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enstargroup.com 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 8Property of Enstar Group – Not for Distribution CONSISTENT ECONOMIC MODEL Strong source of book value growth and internal financing

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enstargroup.com Data from January 2020 – February 1, 2023 1. Excludes Enhanzed Re. 186 opportunities reviewed $64.9bn of net reserves 15 1 deals completed $8.1bn1 of reserves Executing on opportunities that meet our risk parameters and profitability hurdles 9Property of Enstar Group – Not for Distribution ROBUST TRANSACTION PIPELINE Consistent financial and operational discipline applied to pipeline to drive returns

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enstargroup.com 1. TIR and RLE leverage factors are calculated as average investable assets and average net loss reserves, respectively, for the year ended December 31, 2022, divided by opening equity as of December 31, 2021. 2. Non-cash items include amortization of net deferred charge assets. TOTAL INVESTMENT RETURN ("TIR") Leverage Factor1: 3.5x RUN-OFF LIABILITY EARNINGS ("RLE") Leverage Factor1: 2.1x EXPENSES & OTHER (INC. NON-CASH2) Return On Equity 10Property of Enstar Group – Not for Distribution RETURN ON EQUITY ("ROE") COMPONENTS Generating attractive returns

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enstargroup.com Investable Assets1 ($bn) Net Loss Reserves ($bn) CAGR 16.9% 11Property of Enstar Group – Not for Distribution 1. Investable Assets is the sum of total investments, cash and cash equivalents, restricted cash and cash equivalents and funds held. CAGR 14.1% A GROWING BALANCE SHEET A platform for delivering balanced and sustainable growth through investable assets and reserves

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enstargroup.com THE ENSTAR EFFECT 12Property of Enstar Group – Not for Distribution CLAIMS 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 equitably settlements quickly to mitigate exposures and reduce claims handling expense • Proven and successful claims execution drives P&C industry outperformance 02 04 CLAIMS INDIRECTLY MANAGED (Oversight) THE ENSTAR EFFECT For most insurance companies, claims experience is an expense item. For Enstar, driving superior claims outcomes is a major competitive advantage 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 • Independent view of claims and reserve adequacy 03

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enstargroup.com 13Property of Enstar Group – Not for Distribution LOSS RESERVE OUTPERFORMANCE Enstar Loss Reserve Outperformance vs US P&C Industry1,2 Five Years Ended 2021 Enstar delivered 2.7% better net loss reserve outcomes on our Run-off segment General Casualty $4.3 Workers' Compensation $2.2 Asbestos & Environmental $2.0 All Other $3.5 Enstar 2022 Year-End Loss Reserves3 ($ in billions) 2.4% 5.9% 8.4% 2.7% General Casualty Workers' Compensation Asbestos & Environmental Total Run-Off Segment Total $12bn 1. We calculated the change in estimates of net ultimate losses for the last 5 calendar years divided by average net loss reserves on our three 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 for the five-year period ended 2021 was as follows: i) General Casualty – Enstar (0.7)%, Industry (3.2)%; ii) Workers' Compensation – Enstar 10.3%, Industry 4.4%; iii) Asbestos & Environmental – Enstar 0.4%, Industry (8.1)%; and iv) Total Run-off – Enstar 3.4%, Industry 0.7%. 3. Net OLR and IBNR loss reserves and ALAE for Enstar's Run-off segment.

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enstargroup.com 29 year history operating in run-off space 115 total acquisitive transactions completed to date 14Property of Enstar Group – Not for Distribution 15 18 27 32 38 46 59 73 85 94 106 120 131 153 170 165 209 294 329 246 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Book value per common share in USD HISTORY OF ENHANCING BOOK VALUE

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enstargroup.com 15Property of Enstar Group – Not for Distribution (5.0)% 25.5 % 38.4 % 7.9 % (15.6)% 10.2 % 2.4 % 18.8 % 41.9 % 10.1 % (1.1)% 14.4 % 2018 2019 2020 2021 2022 Average 2018- 2022 Return on Equity and Adjusted Return on Equity\* Return on Equity Adjusted Return on Equity\* Targeting long-term Adjusted ROE low to mid-teens\*\* 5-YEAR ROE AND ADJUSTED ROE\* \* Non-GAAP measure; refer to slides 22 to 24 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 investments 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 Adjusted ROE to 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.

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enstargroup.com Significant Liquidity to Support Growth • $1.3bn of cash and cash equivalents • $600m of unused revolving credit facility capacity Well-Capitalized with Moderate Leverage • 28.0% financial leverage, in line with 25% - 30% long-term target • Leverage ratio increase due to unrealized losses on fixed income investments • FY21 Solvency ratio of 179%, has increased as of FY22 • Over 5-years, BSCR (solvency) year-end range 170% - 204%; above Bermuda BSCR minimum targets Ratings1 • BBB with positive outlook by S&P (ICR) and BBB+ with stable outlook by Fitch (IDR) Capacity • Closed Aspen LPT in Q2 22 assuming incremental $1.9bn of net loss reserves • Completed LPT with Argo in Q4 22 assuming $718m of net loss reserves • Announced $1.9bn LPT with QBE in Q1 23; expected to close H1 23 • Announced AUD $360m LPT with RACQ in Q1 23; expected to close H1 23 • Significant capacity remains for additional M&A 16Property of Enstar Group – Not for Distribution 1. Credit ratings are provided by third parties, Standard and 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. CAPACITY FOR GROWTH Well-funded as of 31 December 2022

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enstargroup.com 25 years Average Industry Experience: Paul O'Shea President, Co-founder Years at Enstar: 28 Industry Experience: 35+ years Age: 65 Dominic Silvester CEO & Co-founder Years at Enstar: 29 Industry Experience: 40+ years Age: 62 Orla Gregory Chief Financial Officer Years at Enstar: 19 Industry Experience: 25+ years Age: 48 Paul Brockman Chief Claims Officer Years at Enstar: 10 Industry Experience: 25+ years Age: 50 Audrey Taranto General Counsel Years at Enstar: 10 Industry Experience: 10+ years Age: 43 Nazar Alobaidat Chief Investment Officer Years at Enstar: 6 Industry Experience: 20+ years Age: 45 Matthew Kirk Group Treasurer Years at Enstar: 2 Industry Experience: 25+ years Age: 49 Laurence Plumb Chief of Business Operations Years at Enstar: 2 Industry Experience: 15+ years Age: 39 David Ni Chief Strategy Officer Years at Enstar: 3 Industry Experience: 15+ years Age: 39 Michael Murphy Chief Accounting Officer & Deputy CFO Years at Enstar: 1 Industry Experience: 30+ years Age: 55 Seema Thaper Group Chief Risk Officer Years at Enstar: 3 Industry Experience: 20+ years Age: 42 275+ years Collective Industry Experience : 17Property of Enstar Group – Not for Distribution MANAGEMENT WELL-ALIGNED WITH SHAREHOLDERS Seasoned leadership with exceptional track record of value creation

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18Property of Enstar Group – Not for Distribution APPENDIX enstargroup.com

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enstargroup.com 19Property of Enstar Group – Not for Distribution $19.5bn Total Investable Assets 1 $14.2bn Investment Portfolio 2 $1.3bn Cash and restricted cash 4.40 yrs Average Duration 3 2.47% Book Yield A+ Average Investment Portfolio Credit Rating 4 Investable Assets (As of December 31, 2022) - Composition by Asset Class Funds Held5 Other InvestmentsFixed Maturities Equities Fixed Income, Trading and AFS U.S. government & agency 2.6 % U.K. government 0.4 % Other government 2.4 % Corporate 27.1 % Municipal 1.1 % Residential mortgage-backed 2.8 % Commercial mortgage-backed 5.2 % Asset-backed 4.7 % Structured products 3.0 % Total 49.3 % Other Investments Private equity funds 6.6 % Fixed income funds 2.8 % Private credit funds 1.9 % Hedge funds 2.8 % Equity funds — % CLO equities 0.8 % CLO equity funds 1.0 % Real estate funds 1.0 % Total 16.9 % Equities Publicly traded equities 2.0 % Exchange-traded funds 2.6 % Privately held equities 1.8 % Total 6.4 % Equity Method Investments Cash and Cash Equivalents 1. The sum of total investments, cash and cash equivalents, restricted cash and cash equivalents and funds held. 2. Excludes 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. INVESTMENT PORTFOLIO COMPOSITION

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enstargroup.com 20Property of Enstar Group – Not for Distribution $ millions Three Months Ended December 31, 2022 Three Months Ended December 31, 2021 Year Ended December 31, 2022 Year Ended December 31, 2021 Net premiums earned $14 $41 $66 $245 Net investment income and net realized and unrealized gains (losses) 168 87 (1,159) 429 Other income 2 15 35 42 Net gain on sales of subsidiaries — 11 — 73 Net incurred losses and LAE 271 133 708 231 Policyholder benefit expenses — 3 (25) 3 Amortization of net deferred charge assets (20) (17) (80) (55) Acquisition costs (3) (7) (23) (57) Interest expense (18) (18) (89) (69) General and administrative expenses and net foreign exchange (losses) gains (109) (95) (316) (355) Income tax benefit (expense) 16 (14) 12 (27) (Losses) earnings from equity method investments (86) (8) (74) 93 Net earnings (loss) 235 131 (945) 553 Net loss (earnings) attributable to noncontrolling interests 1 (2) 75 (15) Dividends on preferred shares (9) (9) (36) (36) Net earnings (loss) attributable to Enstar ordinary shareholders $227 $120 $(906) $502 FINANCIAL DATA Summary Income Statement

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enstargroup.com 21Property of Enstar Group – Not for Distribution $ millions December 31, 2022 December 31, 2021 Assets Investable assets $19,540 $21,708 Reinsurance balances recoverable 1,131 1,517 Net deferred charge assets 658 598 Other 825 833 Total Assets $22,154 $24,656 Liabilities Losses and loss adjustment expenses $13,007 $13,258 Future policyholder benefits 1,184 1,502 Defendant asbestos and environmental liabilities 607 638 Debt obligations 1,829 1,691 Other 562 835 Total Liabilities 17,189 17,924 Redeemable noncontrolling interests ("RNCI") 168 179 Shareholders' Equity Ordinary shareholders' equity 4,191 5,813 Series D & E preferred shares 510 510 Noncontrolling interests 96 230 Total Shareholders' Equity 4,797 6,553 Total Liabilities, RNCI & Shareholders' Equity $22,154 $24,656 FINANCIAL DATA Summary Balance Sheet

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enstargroup.com 22Property of Enstar Group – Not for Distribution NON-GAAP MEASURES 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 maturity investments 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 income securities 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 maturity investments and funds held- directly managed, -change in fair value of insurance contracts for which we have elected the fair value option (1), -amortization of fair value adjustments, -net gain/loss on purchase and sales of subsidiaries (if any), -net earnings from discontinued operations (if any), -tax effects of adjustments, 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 maturity investments and funds held-directly managed, -fair value of insurance contracts for which we have elected the fair value option (1), -fair value adjustments, and -net assets of held for sale or disposed subsidiaries classified as discontinued operations (if any) (1) Comprises the discount rate and risk margin components.

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enstargroup.com 23Property of Enstar Group – Not for Distribution (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 as of December 31, 2021, 2020 and 2019), 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. For the Year Ended December 31, 2022 2021 2020 Net (loss) earnings (1) Opening Equity (1) (Adj) ROE Net earnings (1) Opening Equity (1) (Adj) ROE Net earnings (1) Opening Equity (1) (Adj) ROE Net (loss) earnings/Opening equity/ROE (1) $(906) $5,813 (15.6)% $502 $6,326 7.9 % $1,723 $4,490 38.4 % Non-GAAP adjustments: Net realized and unrealized losses on fixed maturity investments and funds held - directly managed / Net unrealized gains on fixed maturity investments and funds held - directly managed (2) 1,181 (89) 210 (560) (306) (277) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) (200) (107) (75) (33) 119 (130) Amortization of fair value adjustments / Fair value adjustments (18) (106) 16 (128) 27 (152) Net gain on purchase and sales of subsidiaries — — (73) — (3) — Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations — — — — (16) (266) Tax effects of adjustments (4) (7) — (21) — 23 — Adjustments attributable to noncontrolling interests (5) (111) — 6 — 13 109 Adjusted net (loss) earnings/Adjusted opening equity/Adjusted ROE\* $(61) $5,511 (1.1)% $565 $5,605 10.1 % $1,580 $3,774 41.9 % RECONCILIATION TO ADJUSTED RETURN ON EQUITY 2022, 2021 and 2020

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enstargroup.com 24Property of Enstar Group – Not for Distribution For the Year Ended December 31, 2019 2018 Net earnings (1) Opening Equity (1) (6) (Adj) ROE Net (loss) earnings (1) Opening Equity (1) (6) (Adj) ROE (in millions of U.S. dollars) Net (loss) earnings/Opening equity/ROE (1) $906 $3,546 25.5 % $(166) $3,295 (5.0)% Non-GAAP adjustments: Net realized and unrealized losses (gains) on fixed maturity investments and funds held - directly managed / Unrealized (losses) gains on fixed maturity investments and funds held - directly managed (2) (516) 227 237 (101) Change in fair value of insurance contracts for which we have elected the fair value option / Fair value of insurance contracts for which we have elected the fair value option (3) 117 (244) 7 (183) Amortization of fair value adjustments / Fair value adjustments 51 (199) 7 (104) Net earnings from discontinued operations / Net assets of entities classified as held for sale and discontinued operations (7) (210) (1) (157) Tax effects of adjustments (4) 36 — (18) — Adjustments attributable to noncontrolling interests (5) 15 86 3 65 Adjusted net (loss) earnings/Adjusted opening equity/Adjusted ROE\* $602 $3,206 18.8 % $69 $2,815 2.4 % (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 as of December 31, 2018), prior to any non-GAAP adjustments. (2) Represents the net realized and unrealized gains and losses 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. (6) The 2017 and 2018 balance sheets have not been restated to reflect the impact of the 2020 StarStone U.S. discontinued operations classification. \* Non-GAAP financial measure. RECONCILIATION TO ADJUSTED RETURN ON EQUITY 2018 and 2019

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