ESGOF / Enstar Group Limited - Preferred Stock - تصريحات هيئة الأوراق المالية والبورصات، التقرير السنوي، بيان الوكيل

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number 001-33289 Enstar Group Limited (Exact name of registrant as specified in its

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 25 NOTIFICATION OF REMOVAL FROM LISTING AND/OR REGISTRATION UNDER SECTION 12(b) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-33289

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 25 NOTIFICATION OF REMOVAL FROM LISTING AND/OR REGISTRATION UNDER SECTION 12(b) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-33289 Enstar Group Limited The Nasdaq Stock Market LLC (Exact name of Issuer as specified in its charter, and name of Exchange where security is listed and/or registered) A.S. C

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): July 2, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

Elk Topco LLC C/O Walkers Corporate (Bermuda) Limited Park Place, 55 Par-la-Ville Road Hamilton, HM11, Bermuda

Exhibit 99.(d)(xix) Form Elk Topco LLC C/O Walkers Corporate (Bermuda) Limited Park Place, 55 Par-la-Ville Road Hamilton, HM11, Bermuda July 2, 2025 [NAME] [ADDRESS] Re: Rollover and Support Agreement ([NAME]) To whom it may concern: This rollover and support agreement, dated as of the date first written above (as amended, restated, modified or supplemented from time to time, and together with all

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

amended and restated BYE-LAWS

  Exhibit 3.1   amended and restated BYE-LAWS   OF   Enstar group limited     For and on behalf of   Conyers Corporate Services (Bermuda) Limited   Secretary   Adopted: 2 July 2025         AMENDED AND RESTATED BYE-LAWS   OF   ENSTAR GROUP LIMITED         TABLE OF CONTENTS   BYE-LAW PAGE     DEFINITIONS 1     POWER TO ISSUE SHARES 3     POWER OF THE COMPANY TO PURCHASE ITS OWN SHARES 3     RIGHTS A

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 4 Enstar Group Limited (Name of the Issuer) Enstar Group

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 4 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Elk Evergreen Investments, LLC Elk Cypress Investments, LLC TSSP Sub-Fund HoldCo, LLC Dominic F. Silvester Elk Topco, LLC Elk Parent Limited E

Sixth Street Completes Acquisition of Enstar Transaction supports leading global insurance group’s next chapter as a private company

Exhibit 99.1 Sixth Street Completes Acquisition of Enstar Transaction supports leading global insurance group’s next chapter as a private company HAMILTON, Bermuda, July 02, 2025 (GLOBE NEWSWIRE) – Enstar Group Limited (“Enstar”) (Nasdaq: ESGR) today announced the closing of its acquisition by investment vehicles managed by affiliates of Sixth Street, a leading global investment firm, for $338.00

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

Changes in Control of Registrant, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Completion of Acquisition or Disposition of Assets

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): July 2, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

As filed with the Securities and Exchange Commission on July 2, 2025

As filed with the Securities and Exchange Commission on July 2, 2025 Registration Statement No.

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): May 1, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number) (

LOSS PORTFOLIO TRANSFER REINSURANCE AGREEMENT THE MEMBERS OF LLOYD’S SYNDICATE 609 FOR THE 2023 AND PRIOR YEARS OF ACCOUNT, ACTING THROUGH THEIR MANAGING AGENT ATRIUM UNDERWRITERS LIMITED (REINSURED) THE MEMBERS OF LLOYD'S SYNDICATE 2008 FOR THE 2025

Exhibit 10.1 LOSS PORTFOLIO TRANSFER REINSURANCE AGREEMENT THE MEMBERS OF LLOYD’S SYNDICATE 609 FOR THE 2023 AND PRIOR YEARS OF ACCOUNT, ACTING THROUGH THEIR MANAGING AGENT ATRIUM UNDERWRITERS LIMITED (REINSURED) and THE MEMBERS OF LLOYD'S SYNDICATE 2008 FOR THE 2025 YEAR OF ACCOUNT, ACTING THROUGH THEIR MANAGING AGENT ENSTAR MANAGING AGENCY LIMITED (REINSURER) CONTENTS 2 Definitions 3 3 Reinsuran

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement March 31, 2025 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement March 31, 2025 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 8 Non-GAAP Measures 9 Reconciliation to Fully Diluted Book Value per Share 11 Reconciliation to Adjusted Return on Equity 12 Reconci

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 Commission File Numbe

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or o

SEVENTH AMENDED AND RESTATED BYE-LAWS OF ENSTAR GROUP LIMITED

SEVENTH AMENDED AND RESTATED BYE-LAWS OF ENSTAR GROUP LIMITED 1. Definitions 1 2. Power to Issue Shares 3 3. Power of the Company to Purchase its Shares 3 4. Rights Attaching to Shares 3 5. Calls on Shares 9 6. Prohibition on Financial Assistance 9 7. Forfeiture of Shares 9 8. Share Certificates 10 9. Fractional Shares 10 10. Register of Members 10 11. Registered Holder Absolute Owner 11 12. Trans

Junior Subordinated Indenture, dated as of March 18, 2025, between the Company and The Bank of New York Mellon, as trustee.

Exhibit 4.1 Execution Version ENSTAR GROUP LIMITED AND THE BANK OF NEW YORK MELLON as TRUSTEE JUNIOR SUBORDINATED INDENTURE Dated as of March 18, 2025 TABLE OF CONTENTS Page ARTICLE 1 DEFINITIONS SECTION 1.1. Certain Terms Defined 1 ARTICLE 2 SECURITIES SECTION 2.1. Forms Generally 9 SECTION 2.2. Form of Trustee’s Certificate of Authentication 9 SECTION 2.3. Amount Unlimited; Issuable in Series 10

First Supplemental Indenture, dated as of March 18, 2025, between the Company and The Bank of New York Mellon, as trustee.

Exhibit 4.2 Execution Version ENSTAR GROUP LIMITED, as ISSUER, AND THE BANK OF NEW YORK MELLON, as TRUSTEE FIRST SUPPLEMENTAL INDENTURE Dated as of March 18, 2025 to JUNIOR SUBORDINATED INDENTURE Dated as of March 18, 2025 7.500% Fixed-Rate Reset Junior Subordinated Notes due 2045 TABLE OF CONTENTS Page ARTICLE I Definitions SECTION 1.1. Conventions 2 SECTION 1.2. Certain Terms Defined 2 SECTION 1

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

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 18, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

Financial Statements and Exhibits, Other Events

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 10, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

Enstar Group Limited Announces Any And All Cash Tender Offer For Junior Subordinated Notes Due 2040

Exhibit 99.1 Enstar Group Limited Announces Any And All Cash Tender Offer For Junior Subordinated Notes Due 2040 HAMILTON, Bermuda, March 10, 2025 (GLOBE NEWSWIRE) - Enstar Group Limited (“Enstar”) (Nasdaq: ESGR) today announced that it has commenced a cash tender offer (the “Tender Offer”) for any and all of the outstanding 5.750% Fixed-Rate Reset Junior Subordinated Notes due 2040 issued by Enst

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

ENSTAR GROUP LIMITED 2025 ANNUAL INCENTIVE COMPENSATION PROGRAM TABLE OF CONTENTS

Exhibit 10.1 ENSTAR GROUP LIMITED 2025 ANNUAL INCENTIVE COMPENSATION PROGRAM TABLE OF CONTENTS Page 1. PURPOSE............................................................................................................................. 3 2. DEFINITIONS........................................................................................................................ 3 3. BONUS POOL…...........

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement December 31, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Book Value Per Share & Return On Equity 7 Conso

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement December 31, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Book Value Per Share & Return On Equity 7 Consolidated Results by Segment 8 Ultimate Losses % Acquired Losses by Acquisition Year 12 Adjusted Ultimate Losses % Acquired Losses 13 Capital Position &

RESTRICTED STOCK UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN

Exhibit 10.32 RESTRICTED STOCK UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN This Restricted Stock Unit Award Agreement (this “Agreement”) is entered into as of the Grant Date (as defined below), by and between the Grantee (as defined below) and Enstar Group Limited (the “Company”). Except as otherwise defined herein, capitalized terms used in

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (I.R.

Insider Trading Policy

Insider Trading Policy INTRODUCTION This Insider Trading Policy of Enstar Group Limited and its subsidiaries (the “Company” or “we”) sets forth the policies and guidelines that apply with respect to trading in Company securities by Company personnel.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities

Exhibit 22.1 Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities $350 million of 5.750% Fixed-Rate Reset Junior Subordinated Notes due 2040 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x $500 million of 5.500% Fixed-Rate Reset Junior Subordinated Notes due 2042 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x

ENSTAR GROUP LIMITED

Exhibit 21.1 ENSTAR GROUP LIMITED LISTING OF SUBSIDIARIES(1) As of December 31, 2024 Name Jurisdiction of Incorporation AG Australia Holdings Limited Australia Alpha Insurance NV Belgium B.H. Acquisition Limited Bermuda Brake Systems, Inc. Delaware BWDAC, Inc. Delaware Cavello Bay Reinsurance Limited Bermuda Clarendon National Insurance Company Texas Cranmore (UK) Limited United Kingdom Cranmore (

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): January 13, 2025 Enstar Group Lim

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): January 13, 2025 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numb

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, each of the undersigned agrees that (i) this statement on Schedule 13G has been adopted and filed on behalf of each of them and (ii) all future amendments to such statement on Schedule 13G will, unless written notice to the contrary is delivered as described below, be jointly

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): December 16, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

[Signature Page to Repayment Letter]

Exhibit 10.1 December 16, 2024 David Ni [***] Re: Accelerated Payments and Potential Repayment Obligations Dear David: This letter agreement (the “Letter Agreement”) memorializes your agreement and understanding with Enstar Group Limited (the “Company”) regarding the following in connection with the anticipated completion of the transactions contemplated by that certain merger agreement (“Merger A

Other Events

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): December 13, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

Enstar Group Limited A.S. Cooper Building, 4th Floor, 26 Reid Street Hamilton HM 11, Bermuda

Exhibit 10.1 Enstar Group Limited A.S. Cooper Building, 4th Floor, 26 Reid Street Hamilton HM 11, Bermuda November 19, 2024 Dominic Silvester c/o Enstar Group Limited A.S. Cooper Building, 4th Floor, 26 Reid Street Hamilton HM 11, Bermuda RE: Extension of Employment Term Dear Dominic, This letter will evidence the agreement of Enstar Group Limited (“Enstar”) and Enstar (EU) Limited to extend the t

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): November 19, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organizati

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement September 30, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Posi

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement September 30, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 10 Non-GAAP Measures 11 Reconciliation to Fully Diluted Book Value per Share 13 Reconciliation to Adjusted Return on Equity 14 R

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 12, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

Financial Statements and Exhibits, Other Events, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): November 6, 2024 ENSTAR GROUP LIMITED (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or Other Jurisdiction of Incorporation) (Commission File Number) (I.

Enstar Shareholders Overwhelmingly Approve Sixth Street Acquisition

Exhibit 99.1 Enstar Shareholders Overwhelmingly Approve Sixth Street Acquisition November 6, 2024 HAMILTON, Bermuda, Nov. 06, 2024 (GLOBE NEWSWIRE) - Enstar Group Limited (“Enstar”) (Nasdaq: ESGR) today announced that it received the necessary shareholder approval for its proposed acquisition by Sixth Street, with Liberty Strategic Capital, J.C. Flowers & Co. LLC, and other institutional investors

Enstar Announces Changes to Executive Leadership Team Appoints Paul Brockman as Chief Commercial Officer Names Adrian Thornycroft as Chief Administrative Officer from May 2025

Exhibit 99.1 Enstar Announces Changes to Executive Leadership Team Appoints Paul Brockman as Chief Commercial Officer Names Adrian Thornycroft as Chief Administrative Officer from May 2025 HAMILTON, Bermuda, October 29 - Enstar Group Limited (“Enstar”) (Nasdaq: ESGR), today announces changes to its executive leadership team in connection with the upcoming retirement of Orla Gregory, President, at

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

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): October 29, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numb

[Signature page follows]

Exhibit 10.1 October 29, 2024 Paul Brockman c/o Enstar (US) Inc. 150 Second Avenue North Third Floor St. Petersburg, FL 33701 Dear Paul: This acknowledgement letter (this “Letter”) confirms the parties’ mutual understanding of the terms applicable to the expiration of your role as Interim CEO of Enstar (EU) Limited (“Enstar EU”), your continued employment with Enstar (US) Inc. (“Enstar US”), and y

ESGR / Enstar Group Limited / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Enstar Group Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G3075P101 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): October 30, 2024 ENSTAR GROUP LIMITED (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or Other Jurisdiction of Incorporation) (Commission File Number) (I.

Table 1: Transaction Valuation

Calculation of Filing Fee Tables Table 1: Transaction Valuation Proposed Maximum Aggregate Value of Transaction Fee Rate Amount of Filing Fee Fees to be Paid 1 $ 399,164,000.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 3 Enstar Group Limited (Name of the Issuer) Enstar Group

SC 13E3/A 1 tm2420342-22sc13e3a.htm SC 13E3/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 3 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Deer Ltd. Deer Merger Sub Ltd. Elk Evergreen Investments, LLC Elk Cypress Investments, LLC TSSP

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 3)

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 3) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 1

Filing Fee Table

Calculation of Filing Fee Tables Table 1: Transaction Valuation Transaction Valuation Fee Rate Amount of Filing Fee Fees to be Paid 1 $ 399,164,000.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 2)

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 2) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 2 Enstar Group Limited (Name of the Issuer) Enstar Group

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 2 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Deer Ltd. Deer Merger Sub Ltd. Elk Evergreen Investments, LLC Elk Cypress Investments, LLC TSSP Sub-Fund HoldCo, LLC Dominic F. Silvester Elk

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 1 Enstar Group Limited (Name of the Issuer) Enstar Group

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Amendment No. 1 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Deer Ltd. Deer Merger Sub Ltd. Elk Evergreen Investments, LLC Elk Cypress Investments, LLC TSSP Sub-Fund HoldCo, LLC Dominic F. Silvester Elk

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 1

AMENDMENT NO. 1 TO AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT

Exhibit 10.1 AMENDMENT NO. 1 TO AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT This AMENDMENT NO. 1 TO AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT (this “Amendment”) is entered into as of September 9, 2024 by and among ENSTAR GROUP LIMITED (“Enstar”), as Parent and a Borrower, KENMARE HOLDINGS LTD., ENSTAR (US ASIA-PAC) HOLDINGS LIMITED, ENSTAR HOLDINGS (US) LLC and CAVELLO BAY REINSURANCE LI

AMENDMENT NO. 1 TO AMENDED AND RESTATED LETTER OF CREDIT FACILITY AGREEMENT

Exhibit 10.2 AMENDMENT NO. 1 TO AMENDED AND RESTATED LETTER OF CREDIT FACILITY AGREEMENT This AMENDMENT NO. 1 TO AMENDED AND RESTATED LETTER OF CREDIT FACILITY AGREEMENT (this “Amendment”) is entered into as of September 9, 2024 by and among CAVELLO BAY REINSURANCE LIMITED, as Borrower, ENSTAR GROUP LIMITED, KENMARE HOLDINGS LTD., ENSTAR (US ASIA-PAC) HOLDINGS LIMITED and ENSTAR HOLDINGS (US) LLC,

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): September 9, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

Purchase Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC.

Exhibit (d)(xiv) EXECUTION VERSION PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, ELK EVERGREEN INVESTMENTS, LLC and ELK CYPRESS INVESTMENTS, LLC November 8, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of November 8, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), Elk Evergreen Investments, LLC, a Delaware limited liability company (“Evergreen Purchaser”), and Elk Cypress Investments, LLC (“Cypress Purchaser” and together with Evergreen Purchaser, the “Purchasers”).

Assignment and Assumption Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC, Flexpoint Asset Opportunity Fund II-A, L.P. and Flexpoint Asset Opportunity Fund II-B, L.P.

Exhibit (d)(xv) EXECUTION VERSION ASSIGNMENT AND ASSUMPTION AGREEMENT This ASSIGNMENT AND ASSUMPTION AGREEMENT is dated as of November 8, 2023 (this “Agreement”) by and among (i) Elk Evergreen Investments, LLC (“Evergreen Assignor”) and Elk Cypress Investments, LLC (“Cypress Assignor” and together with Evergreen Assignor, the “Assignors”), (ii) Flexpoint Asset Opportunity Fund II-A, L.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

Table 1: Transaction Valuation

Calculation of Filing Fee Tables Table 1: Transaction Valuation Proposed Maximum Aggregate Value of Transaction Fee Rate Amount of Filing Fee Fees to be Paid 1 $ 5,175,781,495.

Limited Guarantee dated as of July 29, 2024, by and among Enstar Group Limited and the persons set forth on Schedule A thereto.

Exhibit (b)(ii) Execution Copy Private & Strictly Confidential LIMITED GUARANTEE LIMITED GUARANTEE, dated as of July 29, 2024 (this “Limited Guarantee”), by each of the persons set forth on Schedule A (each, a “Guarantor” and, collectively, the “Guarantors”), in favor of Enstar Group Limited, an exempted company limited by shares existing under the laws of Bermuda (the “Guaranteed Party”).

Discussion Materials of Goldman Sachs & Co. LLC, dated April 10, 2024.

Exhibit (c)(v) STRICTLY PRIVATE & CONFIDENTIAL DRAFT - CONFIDENTIAL INVESTMENT BANKING Project Elk Discussion Materials Goldman Sachs & Co.

Facilities Commitment Letter dated as of July 29, 2024, by and between Elk Bidco Limited and Barclays Bank PLC.

Exhibit (b)(iii) EXECUTION VERSION BARCLAYS 745 Seventh Avenue New York, New York 10019 CONFIDENTIAL July 29, 2024 Elk Bidco Limited c/o Elk Insurance Holdings, LLC 2100 McKinney Ave Suite 1500 Dallas, TX 75201 Attention: Joshua Peck Project Elk Facilities Commitment Letter Ladies and Gentlemen: Elk Bidco Limited, an exempted company incorporated in Bermuda (the “Company” or “you”), formed at the

Discussion Materials of Goldman Sachs & Co. LLC, dated March 26, 2024.

Exhibit (c)(ii) STRICTLY PRIVATE & CONFIDENTIAL INVESTMENT BANKING Project Elk Preliminary Bid Summary Goldman Sachs & Co.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Deer Ltd

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13E-3 RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934 Enstar Group Limited (Name of the Issuer) Enstar Group Limited Deer Ltd. Deer Merger Sub Ltd. Elk Evergreen Investments, LLC Elk Cypress Investments, LLC TSSP Sub-Fund HoldCo, LLC Dominic F. Silvester Elk Bidco Limited El

Equity Commitment Letter dated as of July 29, 2024, by and among Elk Bidco Limited and the persons set forth on Schedule A thereto.

Exhibit (b)(i) Execution Copy Private and Strictly Confidential July 29, 2024 Elk Bidco Limited 2100 McKinney Ave Suite 1500 Dallas, TX 75201 Ladies and Gentlemen: This letter agreement (this “Letter Agreement”) sets forth the commitments of each of the persons set forth on Schedule A (each, a “Fund” and, collectively, the “Funds”), subject to the terms and conditions set forth herein, to purchase, directly or indirectly, certain equity interests of Elk Bidco Limited, an exempted company limited by shares existing under the laws of Bermuda (“Parent”).

Preferred Equity Commitment Letter dated as of July 29, 2024, by and between Elk Bidco Limited and Stone Point Credit Adviser LLC.

Exhibit (b)(iv) Execution Version STONE POINT CREDIT ADVISER LLC 20 Horseneck Lane Greenwich, Connecticut 06830 CONFIDENTIAL July 29, 2024 Elk Bidco Limited c/o Elk Insurance Holdings, LLC 2100 McKinney Ave Suite 1500 Dallas, TX 75201 Attention: Joshua Peck Project Elk Preferred Equity Commitment Letter Ladies and Gentlemen: Elk Bidco Limited, an exempted Bermuda company (the “Company” or “you”),

Discussion Materials of Goldman Sachs & Co. LLC, dated July 28, 2024.*

Exhibit (c)(vi) STRICTLY PRIVATE & CONFIDENTIAL [***] indicates information has been omitted on the basis of a confidential treatment request pursuant to Rule 24b-2 of the Securities Exchange Act of 1934, as amended.

Filing Fee Table

Calculation of Filing Fee Tables Table 1: Transaction Valuation Transaction Valuation Fee Rate Amount of Filing Fee Fees to be Paid 1 $ 5,175,781,495.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

Discussion Materials of Goldman Sachs & Co. LLC, dated April 8, 2024.

Exhibit (c)(iv) STRICTLY PRIVATE & CONFIDENTIAL DRAFT - CONFIDENTIAL INVESTMENT BANKING Project Elk Discussion Materials Goldman Sachs & Co.

Discussion Materials of Goldman Sachs & Co. LLC, dated April 4, 2024.*

Exhibit (c)(iii) STRICTLY PRIVATE & CONFIDENTIAL DRAFT - CONFIDENTIAL [***] indicates information has been omitted on the basis of a confidential treatment request pursuant to Rule 24b-2 of the Securities Exchange Act of 1934, as amended.

ESGR.P / Enstar Group Limited - Preferred Stock / TRIDENT V, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 d878748dsc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. ǂ)* ENSTAR GROUP LIMITED (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Jacqueline Giammarco Stone Point Capital LLC 20 Horseneck Lane Greenwich, C

JOINT FILING AGREEMENT

Exhibit 1 JOINT FILING AGREEMENT The persons below hereby agree that the Schedule 13D to which this agreement is attached as an exhibit, as well as all future amendments to such Schedule 13D, shall be filed jointly on behalf of each of them.

ESGR.P / Enstar Group Limited - Preferred Stock / Flowers J. Christopher - SC 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Sally A. Rocker J.C. Flowers & Co. LLC 767 Fifth Avenue 23rd Floor New York, NY 10153 212-404-6820 With copies to: Gr

ESGR.P / Enstar Group Limited - Preferred Stock / Silvester Dominic Francis Michael - SC 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Audrey Taranto c/o Enstar Group Limited P.O. Box HM 2267, A.S. Cooper Building 26 Reid Street Hamilton, Bermuda, HM 1

JOINT FILING AGREEMENT

Exhibit 6 JOINT FILING AGREEMENT The persons below hereby agree that the Schedule 13D to which this agreement is attached as an exhibit, as well as all future amendments to such Schedule 13D, shall be filed jointly on behalf of each of them.

ESGR.P / Enstar Group Limited - Preferred Stock / TRIDENT V, L.P. - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. ‡)* ENSTAR GROUP LIMITED (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Jacqueline Giammarco Stone Point Capital LLC 20 Horseneck Lane Greenwich, CT 06830 (203) 862-2900 (Name,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (

Rollover and Support Agreement of Frazer Holdings LP

EX-99.4 4 d878632dex994.htm EX-99.4 EXHIBIT 4 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 Frazer Holdings LP 300 Water Street, Suite 200 Montgomery, AL 36104 Re: Rollover and Support Agreement (Frazer Holdings LP) To whom it may concern: This rollover and support agreement, dated as of the date first written above (as

Authorization and Designation Letter, dated June 15, 2023, by Alan Waxman

EX-99.2 3 d878632dex992.htm EX-99.2 EXHIBIT 2 June 15, 2023 Securities and Exchange Commission 100 F Street, NE Washington, DC 20549 This letter confirms that Joshua Peck is authorized and designated to sign all securities-related filings under Sections 13 and 16 of the Securities Exchange Act of 1934, as amended, with the Securities and Exchange Commission, including Form ID, on my behalf. This a

ESGR.P / Enstar Group Limited - Preferred Stock / TSSP Sub-Fund HoldCo LLC - SC 13D Activist Investment

SC 13D 1 d878632dsc13d.htm SC 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Joshua Peck c/o Sixth Street Partners, LLC 2100 McKinney Avenue Suite 1500 Dallas,

Rollover and Support Agreement of John J. Oros 1998 Family Trust

EX-99.6 6 d878632dex996.htm EX-99.6 EXHIBIT 6 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 John J. Oros 1998 Family Trust c/o J.C. Flowers & Co. LLC 767 Fifth Ave, 23rd Floor New York, NY 10153 Re: Rollover and Support Agreement (John J. Oros 1998 Family Trust) To whom it may concern: This rollover and support agreemen

Rollover and Support Agreement of Steven D. Arnold

EX-99.9 9 d878632dex999.htm EX-99.9 EXHIBIT 9 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 Steven D. Arnold 1001 Fannin Street, Suite 1250 Houston, TX 77002 Re: Rollover and Support Agreement (Steven D. Arnold) To whom it may concern: This rollover and support agreement, dated as of the date first written above (as ame

Joint Filing Agreement

EX-99.1 2 d878632dex991.htm EX-99.1 EXHIBIT 1 JOINT FILING AGREEMENT The persons below hereby agree that the Schedule 13D to which this agreement is attached as an exhibit, as well as all future amendments to such Schedule 13D, shall be filed jointly on behalf of each of them. This agreement is intended to satisfy the requirements of Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934.

Rollover and Support Agreement of David Walsh

EX-99.8 8 d878632dex998.htm EX-99.8 EXHIBIT 8 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 David Walsh Foley & Lardner P.O. Box 1497 Madison, WI 53701 Re: Rollover and Support Agreement (David Walsh) To whom it may concern: This rollover and support agreement, dated as of the date first written above (as amended, resta

Rollover and Support Agreement of Dominic Silvester

EX-99.10 10 d878632dex9910.htm EX-99.10 EXHIBIT 10 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 Dominic Silvester Waterloo House Apartment #4 100 Pitts Bay Road Hamilton, HM 08, Bermuda Re: Rollover and Support Agreement (Dominic Silvester) To whom it may concern: This rollover and support agreement, dated as of the da

Rollover and Support Agreement of Hyman 2018 Family Trust

EX-99.7 7 d878632dex997.htm EX-99.7 EXHIBIT 7 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 Hyman 2018 Family Trust 5 Dolma Road Scarsdale, New York 10583 Re: Rollover and Support Agreement (Hyman 2018 Family Trust) To whom it may concern: This rollover and support agreement, dated as of the date first written above (as

Rollover and Support Agreement of J. Christopher Flowers

EX-99.5 5 d878632dex995.htm EX-99.5 EXHIBIT 5 ELK TOPCO LLC C/O WALKERS CORPORATE (BERMUDA) LIMITED PARK PLACE, 55 PAR-LA-VILLE ROAD HAMILTON, HM11, BERMUDA July 29, 2024 J. Christopher Flowers c/o J.C. Flowers & Co. LLC 767 Fifth Ave, 23rd Floor New York, NY 10153 Re: Rollover and Support Agreement (J. Christopher Flowers) To whom it may concern: This rollover and support agreement, dated as of t

Press Release of the Company, dated July 29, 2024

Exhibit 99.3 Date: July 29, 2024 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar to Be Acquired by Sixth Street for $5.1 Billion Enstar shareholders to receive $338.00 per share in cash Strong alignment between Enstar and Sixth Street to ensure continuity of Enstar strategy HAMILTON, Bermuda, July 29, 2024 – Enstar Group Limited (“Enstar”) (Nasdaq: ESGR)

Transition Agreement, dated as of July 29, 2024, by and among Ms. Gregory and the Company.

Exhibit 10.1 TRANSITION AGREEMENT This TRANSITION AGREEMENT (this “Agreement”) is made and entered into by and between Enstar Group Limited (the “Company”) and Orla M. Gregory (“Executive”) as of July 29, 2024. BACKGROUND WHEREAS, Executive and the Company are currently parties to that certain Amended and Restated Employment Agreement, dated as of January 21, 2020, as amended as of September 16, 2

Investor Financial Supplement, dated July 29, 2024.

Exhibit 99.2 Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement June 30, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 10 Non - GAAP Measures 11 Reconciliation to Fully Diluted Book Value per Share 13 Reconciliation to Adjusted Return on E

Transition Agreement, dated as of July 29, 2024, by and among Ms. Gregory and the Company.

Exhibit 10.1 TRANSITION AGREEMENT This TRANSITION AGREEMENT (this “Agreement”) is made and entered into by and between Enstar Group Limited (the “Company”) and Orla M. Gregory (“Executive”) as of July 29, 2024. BACKGROUND WHEREAS, Executive and the Company are currently parties to that certain Amended and Restated Employment Agreement, dated as of January 21, 2020, as amended as of September 16, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): July 29, 2024 ENSTAR GROUP LIMITED

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): July 29, 2024 ENSTAR GROUP LIMITED (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or Other Jurisdiction of Incorporation) (Commission File Number) (I.

Press Release of the Company, dated July 29, 2024.

Exhibit 99.1 Press Release Date:July 29, 2024 For Release: Immediately Contact: Enstar Communications Telephone: +1 (441) 292-3645 Enstar Group Limited Reports Second Quarter 2024 Results • Enstar to be Acquired by Sixth Street-led Consortium for $5.1 Billion • Net Income Attributable to Enstar Ordinary Shareholders of $126 Million; Return on Equity of 2.5% Primarily Driven by Positive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): July 29, 2024 ENSTAR GROUP LIMITED

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 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): July 29, 2024 ENSTAR GROUP LIMITED (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or Other Jurisdiction of Incorporation) (Commission File Number) (I.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

Agreement and Plan of Merger, dated as of July 29, 2024, by and among Enstar Group Limited, Deer Ltd., Deer Merger Sub, Ltd. Elk Bidco Limited, and Elk Merger Sub Limited.

Exhibit 2.1 Execution Version AGREEMENT AND PLAN OF MERGER dated as of JULY 29, 2024 by and among ELK BIDCO LIMITED, ELK MERGER SUB LIMITED, ENSTAR GROUP LIMITED, DEER LTD., AND DEER MERGER SUB LTD. TABLE OF CONTENTS Page Article I DEFINITIONS 3 Section 1.1 Definitions 3 Article II THE MERGERS 3 Section 2.1 The First Merger 3 Section 2.2 The Second Merger 4 Section 2.3 The Third Merger 5 Section 2

Agreement and Plan of Merger, dated as of July 29, 2024, by and among Enstar Group Limited, Deer Ltd., Deer Merger Sub, Ltd. Elk Bidco Limited, and Elk Merger Sub Limited.

Exhibit 2.1 Execution Version AGREEMENT AND PLAN OF MERGER dated as of JULY 29, 2024 by and among ELK BIDCO LIMITED, ELK MERGER SUB LIMITED, ENSTAR GROUP LIMITED, DEER LTD., AND DEER MERGER SUB LTD. TABLE OF CONTENTS Page Article I DEFINITIONS 3 Section 1.1 Definitions 3 Article II THE MERGERS 3 Section 2.1 The First Merger 3 Section 2.2 The Second Merger 4 Section 2.3 The Third Merger 5 Section 2

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement June 30, 2024 ENSTAR GROUP LIMITED

Exhibit 99.2 Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement June 30, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 10 Non - GAAP Measures 11 Reconciliation to Fully Diluted Book Value per Share 13 Reconciliation to Adjusted Return on E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

Enstar to Be Acquired by Sixth Street for $5.1 Billion Enstar shareholders to receive $338.00 per share in cash Strong alignment between Enstar and Sixth Street to ensure continuity of Enstar strategy

Exhibit 99.3 Date: July 29, 2024 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar to Be Acquired by Sixth Street for $5.1 Billion Enstar shareholders to receive $338.00 per share in cash Strong alignment between Enstar and Sixth Street to ensure continuity of Enstar strategy HAMILTON, Bermuda, July 29, 2024 – Enstar Group Limited (“Enstar”) (Nasdaq: ESGR)

Enstar Group Limited Reports Second Quarter 2024 Results

Exhibit 99.1 Press Release Date:July 29, 2024 For Release: Immediately Contact: Enstar Communications Telephone: +1 (441) 292-3645 Enstar Group Limited Reports Second Quarter 2024 Results • Enstar to be Acquired by Sixth Street-led Consortium for $5.1 Billion • Net Income Attributable to Enstar Ordinary Shareholders of $126 Million; Return on Equity of 2.5% Primarily Driven by Positive Investment

Submission of Matters to a Vote of Security Holders

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): June 6, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

AMENDED AND RESTATED EMPLOYMENT AGREEMENT

Exhibit 10.1 AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Amended and Restated Employment Agreement (“Agreement”) is made by and between Enstar (US) Inc., a Delaware corporation (the “Company”), and Nazar Alobaidat (“Executive”). The Company is a subsidiary of Enstar Group Limited (collectively, with its subsidiaries, “Enstar”). 1. Employment Period. The Company hereby continues to employ Execut

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement March 31, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement March 31, 2024 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 8 Non-GAAP Measures 9 Reconciliation to Fully Diluted Book Value per Share 11 Reconciliation to Adjusted Return on Equity 12 Reconci

Amendment No. 2 Employment Agreement

Exhibit 10.2 Amendment No. 2 to Employment Agreement This Amendment No. 2 (this “Amendment”) is entered into on April 4, 2024 (the “Signing Date”) and is effective as of January 12, 2024 (the “Effective Date”), between Enstar (US) Inc., a Delaware corporation (“Company”) and Paul Brockman (“Executive”) and amends the Employment Agreement between Company and Executive entered into January 8, 2018,

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): May 2, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number) (

DATED: 04-April-2024 ENSTAR (EU) LIMITED PAUL BROCKMAN CONTRACT OF EMPLOYMENT

Exhibit 10.3 DATED: 04-April-2024 ENSTAR (EU) LIMITED AND PAUL BROCKMAN CONTRACT OF EMPLOYMENT THIS AGREEMENT is dated 04-April-2024 1. Terms of Employment 1.1 Capitalised terms used in this Agreement are defined below or in Schedule 1. 1.2 Your employment is at all times conditional on you providing satisfactory evidence that you have the legal right to work in the UK and you will notify the Comp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization)

Enstar Group Limited Reports First Quarter 2024 Results

Press Release Date: May 2, 2024 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar Group Limited Reports First Quarter 2024 Results •Net Income Attributable to Enstar Ordinary Shareholders of $119 Million; Return on Equity of 2.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) _____________________________________ Filed by the Registrant x Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): April 4, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities

Exhibit 22.1 Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities $350 million of 5.750% Fixed-Rate Reset Junior Subordinated Notes due 2040 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x $500 million of 5.500% Fixed-Rate Reset Junior Subordinated Notes due 2042 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 22, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

enstargroup.com Q4 2023 Year-End Review February 2024 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information con

enstargroup.com Q4 2023 Year-End Review February 2024 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information contained in this presentation, may include certain forward-looking statements regarding our views with respect to our business, operations, loss reserve

RESTRICTED SHARE UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED DEFERRED COMPENSATION AND ORDINARY SHARE PLAN FOR NON-EMPLOYEE DIRECTORS (1 YEAR VESTING)

RESTRICTED SHARE UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED DEFERRED COMPENSATION AND ORDINARY SHARE PLAN FOR NON-EMPLOYEE DIRECTORS (1 YEAR VESTING) This Restricted Share Unit Award Agreement (this “Agreement”) is entered into as of the Grant Date (as defined below), by and between the Participant (as defined below) and Enstar Group Limited (the “Company”).

ENSTAR GROUP LIMITED POLICY FOR THE RECOVERY OF ERRONEOUSLY AWARDED COMPENSATION ACKNOWLEDGEMENT FORM

Ex 97.1 Policy for the Recovery of Erroneously Awarded Compensation ` TABLE OF CONTENTS 1. Introduction 3 2. Administration 3 3. Definitions 3 4. Repayment of Erroneously Awarded Compensation 4 5. Other Recoupment 5 6. Reporting and Disclosure 5 7. Indemnification Prohibition 5 8. Interpretation 6 9. Effective Date 6 10. Amendment; Termination 6 11. Other Recoupment Rights; No Additional Payments

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (I.R.

RESTRICTED STOCK AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN (1 YEAR VESTING)

RESTRICTED STOCK AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN (1 YEAR VESTING) This Restricted Stock Award Agreement (this “Agreement”) is entered into as of the Grant Date (as defined below), by and between the Participant (as defined below) and Enstar Group Limited (the “Company”).

ENSTAR GROUP LIMITED

Exhibit 21.1 ENSTAR GROUP LIMITED LISTING OF SUBSIDIARIES(1) As of December 31, 2023 Name Jurisdiction of Incorporation AG Australia Holdings Limited Australia Alpha Gamma NV Belgium Alpha Insurance NV Belgium B.H. Acquisition Limited Bermuda Brake Systems, Inc. Delaware BWDAC, Inc. Delaware Cavello Bay Reinsurance Limited Bermuda Clarendon National Insurance Company Texas Cranmore (UK) Limited Un

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 20, 2024 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

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

Press Release Date: February 20, 2024 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar Group Limited Reports Fourth Quarter and 2023 Year-End Results •Full year 2023 Net Income attributable to Enstar Ordinary Shareholders of $1.

enstargroup.com Q4 2023 Year-End Review February 2024 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information con

enstargroup.com Q4 2023 Year-End Review February 2024 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information contained in this presentation, may include certain forward-looking statements regarding our views with respect to our business, operations, loss reserve

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement December 31, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Book Value Per Share & Return On Equity 7 Conso

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement December 31, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Book Value Per Share & Return On Equity 7 Consolidated Results by Segment 8 Prior Period Development (“PPD”) by Acquisition Year 12 Ultimate Losses % Acquired Losses by Acquisition Year 13 Adjusted

ESGR / Enstar Group Limited / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv0853-enstargroupltd.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 5)* Name of issuer: Enstar Group Ltd Title of Class of Securities: Common Stock CUSIP Number: G3075P101 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the

ESGR / Enstar Group Limited / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4 )* Enstar Group LTD (Name of Issuer) Common Stock (Title of Class of Securities) G3075P101 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to de

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): December 20, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

PURCHASE AGREEMENT KENMARE HOLDINGS LTD., TRIDENT V, L.P., TRIDENT V PARALLEL FUND, L.P., TRIDENT V PROFESSIONALS FUND, L.P., DOWLING CAPITAL PARTNERS I, L.P., CAPITAL CITY PARTNERS LLC December 20, 2023 PURCHASE AGREEMENT

Exhibit 10.1 PURCHASE AGREEMENT among KENMARE HOLDINGS LTD., TRIDENT V, L.P., TRIDENT V PARALLEL FUND, L.P., TRIDENT V PROFESSIONALS FUND, L.P., DOWLING CAPITAL PARTNERS I, L.P., and CAPITAL CITY PARTNERS LLC December 20, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of December 20, 2023, by and among Kenmare Holdings Ltd. (“Kenmare”), Trident V, L.P., Trident V Pa

Shareholder Rights Agreement, dated as of November 8, 2023, by and among Enstar Group Limited, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC (incorporated by reference to Exhibit 10.3 to the Company’s Form 8-K filed on November 13, 2023).

Exhibit 10.3 SHAREHOLDER RIGHTS AGREEMENT This SHAREHOLDER RIGHTS AGREEMENT, dated as of November 8, 2023 (this “Agreement”), is made between (i) ENSTAR GROUP LIMITED, a Bermuda exempted company with liability limited by shares (the “Company”), and (ii) ELK EVERGREEN INVESTMENTS, LLC, a Delaware limited liability company, and ELK CYPRESS INVESTMENTS, LLC, a Delaware limited liability company (coll

Purchase Agreement, dated as of November 7, 2023, by and between Enstar Group Limited and Trident Public Equity L.P. (incorporated by reference to Exhibit 10.2 to the Company’s Form 8-K filed on November 13, 2023).

Exhibit 10.2 PURCHASE AGREEMENT between TRIDENT PUBLIC EQUITY LP and ENSTAR GROUP LIMITED November 7, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of November 7, 2023, by and between Trident Public Equity LP, a Delaware limited partnership (“Trident”), and Enstar Group Limited, a Bermuda exempted company (“Enstar”). RECITALS WHEREAS, Trident is the beneficial owne

Purchase Agreement, dated as of November 7, 2023, by and among Enstar Group Limited, Canada Pension Plan Investment Board, and CPPIB Epsilon Ontario Limited Partnership (incorporated by reference to Exhibit 10.1 to the Company’s Form 8-K filed on November 13, 2023).

Exhibit 10.1 PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, CPPIB EPSILON ONTARIO LIMITED PARTNERSHIP and ENSTAR GROUP LIMITED November 7, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of November 7, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), CPPIB Epsilon Ontario Limited Partnership, an O

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): November 7, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numb

Registration Rights Agreement, dated as of November 8, 2023, by and among Enstar Group Limited, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC (incorporated by reference to Exhibit 10.4 to the Company’s Form 8-K filed on November 13, 2023).

Exhibit 10.4 REGISTRATION RIGHTS AGREEMENT This REGISTRATION RIGHTS AGREEMENT, dated as of November 8, 2023 (this “Agreement”), is made among ENSTAR GROUP LIMITED, a Bermuda company (the “Company”), ELK EVERGREEN INVESTMENTS, LLC, a Delaware limited liability company (“Evergreen”), and ELK CYPRESS INVESTMENTS, LLC (together with Evergreen, the “Sixth Street Entities”). A. On November 8, 2023, the

Assignment and Assumption Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC, Flexpoint Asset Opportunity Fund II-A, L.P. and Flexpoint Asset Opportunity Fund II-B, L.P.

EX-99.3 4 tm2330338d1ex99-3.htm EXHIBIT 99.3 Exhibit 99.3 EXECUTION VERSION ASSIGNMENT AND ASSUMPTION AGREEMENT This ASSIGNMENT AND ASSUMPTION AGREEMENT is dated as of November 8, 2023 (this “Agreement”) by and among (i) Elk Evergreen Investments, LLC (“Evergreen Assignor”) and Elk Cypress Investments, LLC (“Cypress Assignor” and together with Evergreen Assignor, the “Assignors”), (ii) Flexpoint A

ESGR / Enstar Group Limited / CANADA PENSION PLAN INVESTMENT BOARD - SC 13D/A Activist Investment

SC 13D/A 1 tm2330338d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Amendment No. 11) Under the Securities Exchange Act of 1934 Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Patrice Walch-Watson Canada Pension Plan Investment Board One Queen Street

Purchase Agreement, dated November 7, 2023, between Canada Pension Plan Investment Board, CPPIB Epsilon Ontario Limited Partnership and Enstar Group Limited

EX-99.1 2 tm2330338d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, CPPIB EPSILON ONTARIO LIMITED PARTNERSHIP and ENSTAR GROUP LIMITED November 7, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of November 7, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), CP

Purchase Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC

EX-99.2 3 tm2330338d1ex99-2.htm EXHIBIT 99.2 Exhibit 99.2 EXECUTION VERSION PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, ELK EVERGREEN INVESTMENTS, LLC and ELK CYPRESS INVESTMENTS, LLC November 8, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of November 8, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organizati

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 7, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numb

Enstar Group Limited Reports Third Quarter 2023 Results

Press Release Date: November 7, 2023 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar Group Limited Reports Third Quarter 2023 Results •Net Earnings of $38 million and Return on Equity of 0.

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement September 30, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Posi

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement September 30, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 10 Non-GAAP Measures 11 Reconciliation to Adjusted Book Value per Share 13 Reconciliation to Adjusted Return on Equity 14 Reconc

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): August 8, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (

Property of Enstar Group – Not for Distribution enstargroup.com Q2 2023 Mid-Year Review August 2023 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral s

Property of Enstar Group – Not for Distribution enstargroup.com Q2 2023 Mid-Year Review August 2023 Enstar Group Overview Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information contained in this presentation, may include certain forward-looking statements regarding our views with res

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Results of Operations and Financial Condition

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): July 28, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement June 30, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position

Enstargroup.com Enstargroup.com Realising Value Investor Financial Supplement June 30, 2023 ENSTAR GROUP LIMITED | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 10 Non-GAAP Measures 11 Reconciliation to Adjusted Book Value per Share 13 Reconciliation to Adjusted Return on Equity 14 Reconciliat

$800,000,000 AMENDED AND RESTATED LETTER OF CREDIT FACILITY AGREEMENT dated as of July 28, 2023 CAVELLO BAY REINSURANCE LIMITED, as Borrower ENSTAR GROUP LIMITED, KENMARE HOLDINGS LTD., ENSTAR (US ASIA-PAC) HOLDINGS LIMITED and ENSTAR HOLDINGS (US) L

Exhibit 10.1 $800,000,000 AMENDED AND RESTATED LETTER OF CREDIT FACILITY AGREEMENT dated as of July 28, 2023 among CAVELLO BAY REINSURANCE LIMITED, as Borrower ENSTAR GROUP LIMITED, KENMARE HOLDINGS LTD., ENSTAR (US ASIA-PAC) HOLDINGS LIMITED and ENSTAR HOLDINGS (US) LLC, as Guarantors The Lenders Party Hereto From Time to Time, NATIONAL AUSTRALIA BANK LIMITED, as Administrative Agent and NATIONAL

Enstar Group Limited Reports Second Quarter 2023 Results

Press Release Date: August 2, 2023 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar Group Limited Reports Second Quarter 2023 Results •Net Earnings of $21 million and Return on Equity of 0.

ESGR / Enstar Group Limited / CANADA PENSION PLAN INVESTMENT BOARD - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Amendment No. 10) Under the Securities Exchange Act of 1934 Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Patrice Walch-Watson Canada Pension Plan Investment Board One Queen Street East, Suite 2500 Toronto, ON M5C 2W5 Cana

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Submission of Matters to a Vote of Security Holders

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): May 30, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT dated as of May 30, 2023 ENSTAR GROUP LIMITED, as Parent ENSTAR GROUP LIMITED KENMARE HOLDINGS LTD. ENSTAR (US ASIA-PAC) HOLDINGS LIMITED ENSTAR HOLDINGS (US) LLC and CAVELLO BAY REINSURANCE LIMITED, as

Exhibit 10.1 $800,000,000 AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT dated as of May 30, 2023 between ENSTAR GROUP LIMITED, as Parent ENSTAR GROUP LIMITED KENMARE HOLDINGS LTD. ENSTAR (US ASIA-PAC) HOLDINGS LIMITED ENSTAR HOLDINGS (US) LLC and CAVELLO BAY REINSURANCE LIMITED, as Borrowers, ENSTAR GROUP LIMITED KENMARE HOLDINGS LTD. ENSTAR (US ASIA-PAC) HOLDINGS LIMITED and ENSTAR HOLDINGS (US

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement March 31, 2023 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 8 Non-GAAP Mea

a2023q1-investorfinancia enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement March 31, 2023 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 5 Consolidated Results by Segment 6 Capital Position & Credit Ratings 8 Non-GAAP Measures 9 Reconciliation to Adjusted Book Value per Share 11 Reconciliation to Adjusted Return on Equity 12 Reconciliation to A

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): May 4, 2023 Enstar Group Limited

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): May 4, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number) (

Enstar Group Limited Reports First Quarter 2023 Results

Press Release Date: May 4, 2023 Contact: Enstar Communications For Release: Immediately Telephone: +1 (441) 292-3645 Enstar Group Limited Reports First Quarter 2023 Results •Net Earnings of $424 million and Return on Equity of 9.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization)

Employment Agreement

Exhibit 10.2 Employment Agreement This Employment Agreement (“Agreement”) is made by and between Enstar (US) Inc., a Delaware corporation (the “Company”), and DAVID NI (“Executive”). The Company is a subsidiary of Enstar Group Limited (collectively, with its subsidiaries, “Enstar”). This Agreement is effective as of July 1, 2019 (“Effective Date”). 1. Employment Period. The Company hereby employs

You’ve Exceeded the SEC’s Traffic Limit

Exhibit 10.3 AMENDMENT NO. 1 to EMPLOYMENT AGREEMENT This Amendment No. 1 (this “Amendment”) is dated and effective as of February 4, 2022 (the “Amendment Date”), between Enstar (US) Inc. (the “Company”) David Ni (“Executive”) and amends the Employment Agreement between the Company and Executive that was effective as of July 1, 2019 (the “Current Employment Agreement”). BACKGROUND Whereas, the Com

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) _____________________________________ Filed by the Registrant x Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Defin

Purchase Agreement, dated March 23, 2023, between Enstar Group Limited and Canada Pension Plan Investment Board (incorporated by reference to Exhibit 10.1 to the Company’s Form 8-K filed on March 28, 2023).

Exhibit 10.1 PURCHASE AGREEMENT between CANADA PENSION PLAN INVESTMENT BOARD and ENSTAR GROUP LIMITED March 23, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of March 23, 2023 by and between Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), and Enstar Group Limited, a Bermuda exempted company (“Enstar”). RECITALS WHEREAS, CPPIB i

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 23, 2023 Enstar Group Limit

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 23, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

EMPLOYMENT AGREEMENT

Exhibit 10.2 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made by and between Enstar (US) Inc., a Delaware corporation (the “Company”), and Matthew Kirk (“Executive”). The Company is a subsidiary of Enstar Group Limited (collectively, with its subsidiaries, “Enstar”). 1.Employment Period. The Company hereby continues to employ Executive for the period commencing on the date Exec

PURCHASE AGREEMENT CANADA PENSION PLAN INVESTMENT BOARD ENSTAR GROUP LIMITED March 23, 2023 PURCHASE AGREEMENT

Exhibit 99.1 PURCHASE AGREEMENT between CANADA PENSION PLAN INVESTMENT BOARD and ENSTAR GROUP LIMITED March 23, 2023 PURCHASE AGREEMENT This Purchase Agreement (this “Agreement”) is dated as of March 23, 2023 by and between Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), and Enstar Group Limited, a Bermuda exempted company (“Enstar”). RECITALS WHEREAS, CPPIB i

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment No. 1) 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 2, 2023

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment No. 1) 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 2, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Com

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Exhibit 10.3 Amendment No. 1 to Employment Agreement This Amendment No. 1 (this “Amendment”) is entered into on March 21, 2023 (the “Effective Date”), between Enstar (US) Inc., a Delaware corporation (“Company”) and Paul Brockman (“Executive”) and amends the Employment Agreement between Company and Executive entered into January 8, 2018 (the “Current Employment Agreement”). BACKGROUND WHEREAS, Com

AMENDMENT NO. 3 AMENDED AND RESTATED EMPLOYMENT AGREEMENT

Exhibit 10.1 AMENDMENT NO. 3 to AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Amendment No. 3 (this “Amendment”) is entered into on March 21, 2023, between Enstar Group Limited, a Bermuda corporation (“Company”) and Orla M. Gregory (“Executive”) and amends the Amended and Restated Employment Agreement between Company and Executive entered into January 21, 2020, which was amended on September 16,

ESGR / Enstar Group Limited / CANADA PENSION PLAN INVESTMENT BOARD - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Amendment No. 9) Under the Securities Exchange Act of 1934 Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Patrice Walch-Watson Canada Pension Plan Investment Board One Queen Street East, Suite 2500 Toronto, ON M5C 2W5 Canad

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 6, 2023 Enstar Group Limite

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 6, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

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 2, 2023 Enstar Group Limite

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 2, 2023 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

You’ve Exceeded the SEC’s Traffic Limit

Exhibit 25.6 = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) || THE BANK OF NE

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Exhibit 25.1 = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) || THE BANK OF NE

ENSTAR FINANCE LLC, as Issuer ENSTAR GROUP LIMITED, as Guarantor [ ], as TRUSTEE SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Finance LLC

Exhibit 4.16 ENSTAR FINANCE LLC, as Issuer ENSTAR GROUP LIMITED, as Guarantor AND [ ], as TRUSTEE SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Finance LLC, Enstar Group Limited and [ ], as Trustee: Section of the Act Section of Indenture 310(a)(1) and (2) 6.8 310(a)(3) and (4) Inapplica

As filed with the Securities and Exchange Commission on March 2, 2023

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on March 2, 2023 Registration No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A. Name of issuer or person filing (“Filer”): Enstar Group Limited B. This is (select one): ☒ an origin

ENSTAR GROUP LIMITED [ ], as TRUSTEE JUNIOR SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Group Limited and [ ], as Trustee:

Exhibit 4.14 ENSTAR GROUP LIMITED AND [ ], as TRUSTEE JUNIOR SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Group Limited and [ ], as Trustee: Section of the Act Section of Indenture 310(a)(1) and (2) 6.8 310(a)(3) and (4) Inapplicable 310(b) 6.9 311(a) 6.12 311(b) 6.12 312(a) 4.1 and 4.2

ENSTAR FINANCE LLC, as Issuer ENSTAR GROUP LIMITED, as Guarantor [ ], as TRUSTEE SENIOR INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Finance LLC, Enst

Exhibit 4.15 ENSTAR FINANCE LLC, as Issuer ENSTAR GROUP LIMITED, as Guarantor AND [ ], as TRUSTEE SENIOR INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Finance LLC, Enstar Group Limited and [ ], as Trustee: Section of the Act Section of Indenture 310(a)(1) and (2) 6.8 310(a)(3) and (4) Inapplicable 31

ENSTAR GROUP LIMITED [ ], as TRUSTEE SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Group Limited and [ ], as Trustee:

Exhibit 4.13 ENSTAR GROUP LIMITED AND [ ], as TRUSTEE SUBORDINATED INDENTURE Dated as of [ ], 20[ ] CROSS-REFERENCE SHEET(*) Provisions of Trust Indenture Act and Indenture dated as of [ ], 20[ ], between Enstar Group Limited and [ ], as Trustee: Section of the Act Section of Indenture 310(a)(1) and (2) 6.8 310(a)(3) and (4) Inapplicable 310(b) 6.9 311(a) 6.12 311(b) 6.12 312(a) 4.1 and 4.2 312(b)

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U.S. Securities and Exchange Commission You’ve Exceeded the SEC’s Traffic Limit Your request rate has exceeded the SEC’s maximum allowable requests per second. Your access to SEC.gov will be limited for 10 minutes. Current guidelines limit each user to a total of no more than 10 requests per second, regardless of the number of machines used to submit requests. To ensure that SEC.gov remains

ENSTAR GROUP LIMITED

Exhibit 21.1 ENSTAR GROUP LIMITED LISTING OF SUBSIDIARIES(1) As of December 31, 2022 Name Jurisdiction of Incorporation AG Australia Holdings Limited Australia Alpha Insurance NV Belgium B.H. Acquisition Limited Bermuda Brake Systems, Inc. Delaware BWDAC, Inc. Delaware Cavello Bay Reinsurance Limited Bermuda Clarendon National Insurance Company Texas Cranmore (UK) Limited United Kingdom Cranmore (

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Exhibit 22.1 Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities $350 million of 5.750% Fixed-Rate Reset Junior Subordinated Notes due 2040 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x $500 million of 5.500% Fixed-Rate Reset Junior Subordinated Notes due 2042 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (I.R.

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a2022q4-ex991financialst INRE FUND, L.P. FINANCIAL STATEMENTS For the year ended December 31, 2020 INRE FUND, L.P. – FINANCIAL STATEMENTS Contents 1 Report of Independent Auditors 2 Statement of Assets and Liabilities 4 Condensed Schedule of Investments 5 Statement of Operations 17 Statement of Changes in Partners’ Capital 18 Statement of Cash Flows 19 Notes to the Financial Statements 21 Ernst &

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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 of incorporation) (Commission File Number)

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Exhibit 18.1 March 1, 2023 Board of Directors Enstar Group Limited Windsor Place 22 Queen Street Hamilton HM JX, Bermuda Dear Directors: We are providing this letter to you for inclusion as an exhibit to Enstar Group Limited’s (the “Company”) Annual Report on Form 10-K for the year ended December 31, 2022 (the “Form 10-K”) pursuant to Item 601 of Regulation S-K. We have audited the consolidated fi

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

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Enstargroup.com Q4 2022 Review March 2023 Enstar Group Overview Realising Value Property of Enstar Group – Not for Distribution 2 INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respect to information

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SC 13G/A 1 tv0829-enstargroupltd.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 4)* Name of issuer: Enstar Group Ltd. Title of Class of Securities: Common Stock CUSIP Number: G3075P101 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate th

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3 )* Enstar Group LTD (Name of Issuer) Common Stock (Title of Class of Securities) G3075P101 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sched

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Amendment No. 8) Under the Securities Exchange Act of 1934 Enstar Group Limited (Name of Issuer) Ordinary Shares, par value $1.00 per share (Title of Class of Securities) G3075 P101 (CUSIP Number) Patrice Walch-Watson Canada Pension Plan Investment Board One Queen Street East, Suite 2500 Toronto, ON M5C 2W5 Canad

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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): November 3, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numb

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement September 30, 2022 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 4 Consolidated Results by Segment 5 Capital Position & Credit Ratings 9 Non-GAAP

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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): August 18, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Numbe

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Enstargroup.com Mid-Year Review August 2022 Enstar Group Overview Realising Value Property of Enstar Group – Not for Distribution 2enstargroup.com INFORMATION REGARDING FORWARD-LOOKING STATEMENTS This presentation, and oral statements made with respe

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Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

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): August 9, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement June 30, 2022 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 4 Consolidated Results by Segment 5 Capital Position & Credit Ratings 9 Non-GAAP Meas

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Enstar Group Limited Reports Second Quarter Results

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AMENDED AND RESTATED EMPLOYMENT AGREEMENT

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Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): July 1, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

AMENDMENT NO. 2 AMENDED AND RESTATED EMPLOYMENT AGREEMENT

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ENSTAR GROUP LIMITED (Exact name of registrant as specified in its charter)

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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A. Name of issuer or person filing (?Filer?): Enstar Group Limited B. This is (select one): x an origin

ENSTAR GROUP LIMITED AMENDED AND RESTATED 2016 EQUITY INCENTIVE PLAN ENSTAR GROUP LIMITED AMENDED AND RESTATED 2016 EQUITY INCENTIVE PLAN SECTION 1 - PURPOSE

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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): June 1, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

ESGR / Enstar Group Ltd. / STONE POINT CAPITAL LLC - SC 13D/A Activist Investment

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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): May 9, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number) (

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Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

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): May 5, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number) (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization)

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement March 31, 2022 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 4 Consolidated Results by Segment 5 Capital Position & Credit Ratings 7 Non-GAAP Mea

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement March 31, 2022 | enstargroup.com 2 Table of Contents Page Explanatory Notes 3 Financial Highlights 4 Consolidated Results by Segment 5 Capital Position & Credit Ratings 7 Non-GAAP Measures 8 Reconciliation to Adjusted Book Value per Share 10 Reconciliation to Adjusted Return on Equity 11 Reconciliation to Adjusted Run-off Liabiliti

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) _____________________________________ Filed by the Registrant x Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Defin

Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant

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 15, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number

[KPMG Letterhead]

Exhibit 16.1 [KPMG Letterhead] March 21, 2022 Securities and Exchange Commission Washington, D.C. 20549 Ladies and Gentlemen We were previously principal accountants for Enstar Group Limited and, under the date of February 24, 2022, we reported on the consolidated financial statements of Enstar Group Limited as of and for the years ended December 31, 2021 and 2020, and the effectiveness of interna

Regulation FD Disclosure, Financial Statements and Exhibits

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 7, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Number)

enstargroup.com ENSTAR GROUP LIMITED AIFA March 2022 DISCLAIMER enstargroup.com Property of Enstar Group – Not for Distribution 2 Cautionary Statement This presentation contains certain forward-looking statements within the meaning of the Private Sec

EX-99.1 2 a2022esgraifapresentatio.htm EX-99.1 enstargroup.com ENSTAR GROUP LIMITED AIFA March 2022 DISCLAIMER enstargroup.com Property of Enstar Group – Not for Distribution 2 Cautionary Statement This presentation 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

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 Commission File Number 001-33289 ENSTAR GROUP LIMITED (Exact name of Registrant as specified in its charter) BERMUDA N/A (State or other jurisdiction of incorporation or organization) (I.R.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 24, 2022 Enstar Group Limited (Exact name of registrant as specified in its charter) Bermuda 001-33289 N/A (State or other jurisdiction of incorporation) (Commission File Num

Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities

Exhibit 22.1 Enstar Group Limited Subsidiary Guarantors and Issuers of Guaranteed Securities $350 million of 5.750% Fixed-Rate Reset Junior Subordinated Notes due 2040 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x $500 million of 5.500% Fixed-Rate Reset Junior Subordinated Notes due 2042 Issuer Guarantor Enstar Finance LLC x Enstar Group Limited x

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement December 31, 2021 | 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 Pri

enstargroup.com ENSTAR GROUP LIMITED Investor Financial Supplement December 31, 2021 | 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 Adju