Sec Form 4 Filing - Gregory Orla @ Enstar Group LTD - 2023-12-08

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Gregory Orla 2. Issuer Name and Ticker or Trading Symbol Enstar Group LTD [ ESGR] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) President (Last) (First) (Middle) C/O ENSTAR GROUP LIMITED, WINDSOR PLACE, 3RD FLOOR, 22 QUEEN ST. 3. Date of Earliest Transaction (MM/DD/YY) 12/08/2023 (Street) HAMILTON, D0HM 11 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Ordinary Shares 12/08/2023 M( 1 ) 20,000 A $ 147.75 83,496 ( 2 ) D Ordinary Shares 12/08/2023 D( 1 ) 20,000 D $ 285.14 63,496 ( 2 ) D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Numb er of Shares Cash-Settled Stock Appreciation Right $ 147.75 12/08/2023 M( 1 ) 20,000 06/09/2015 06/09/2024 Ordinary Shares ( 3 ) 20,000 $ 0 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Gregory Orla C/O ENSTAR GROUP LIMITED WINDSOR PLACE, 3RD FLOOR, 22 QUEEN ST. HAMILTON, D0HM 11 X President Signatures /s/ Audrey B. Taranto by power of attorney 12/08/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Exercise of the Cash-Settled Stock Appreciation Rights (the "SARs") is reported as the simultaneous purchase and sale to the issuer of the number of ordinary shares for which the SARs were exercised. Pursuant to their terms, the SARs were only exercisable in cash and the reporting person did not receive any ordinary shares. ( 2 )Includes 13,465 Restricted Share Units that vest in three approximately equal annual installments beginning on March 20, 2024. ( 3 )The SARs are settled in cash, and the reporting person will not receive issuer ordinary shares upon exercise.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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