Amendment No. 3 to the Amended and Restated Employment Agreement, dated March 21, 2023, between the Company and Orla Gregory

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, 2021 by Amendment No. 1 and on July 1, 2022 by Amendment No. 2 (the “Current Employment Agreement”).

NOW, THEREFORE, in consideration of the premises and the mutual agreements contained herein and intending to be legally bound hereby, the parties hereto agree as follows:

1.Title. Effective as of the date of this Amendment, Executive has agreed to serve as the President of Company. Executive shall perform such duties and shall have such authority consistent with the position of President as may from time to time be specified by the Chief Executive Officer of Company, acting reasonably. Executive shall no longer hold the position or title of Chief Financial Officer nor the designation of “principal financial officer” of Company.

2.Good Reason. Executive and Company agree and acknowledge that the change to Executive’s capacity and duties described in Section 1 above shall not constitute “Good Reason” as defined in Section 4.4(c) of the Current Employment Agreement and Executive is not entitled to any compensation or damages of any kind because of such changes.

3.Base Compensation. In Section 3.1 of the Current Employment Agreement, Executive’s annual base salary shall change from $1,200,000 to $1,400,000 effective April 1, 2023.

4.No Other Changes to Compensation. Except for Section 3 of this Amendment No. 3 regarding the change to annual base salary, there shall be no changes to Executive’s compensation and benefits under the Current Employment Agreement, which shall remain in full force and effect.

5.Counterparts. This Amendment may be executed in several counterparts, each of which shall be deemed to be an original but all of which together will constitute one and the same instrument. Facsimile or PDF signatures shall be deemed as effective as originals.