Company: KG
Filing Date: 2025-03-26
Form Type: 424B3
Source: 0001104659-25-028251
Chunk: 603

Company: Kestrel Group Ltd
Filing Date: 2025-03-26
Form: 424B3
Chunk 603
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 Partnership, Agency or Joint Venture           
 ​                                                 | ​ | ​ | ​    | ​ | B-3-11 | ​ | ​ |

B-3-2

TABLE OF CONTENTS

### VOTING AND SUPPORT AGREEMENT
This VOTING AND SUPPORT AGREEMENT (this “ Agreement ”) is dated as of December 29, 2024, by and between Kestrel Group LLC, a Delaware limited liability company (the “ Company ”), and the undersigned (the “ Shareholder ”), a holder of Parent Shares (as defined below). The Company and the Shareholder are each referred to in this Agreement as a “ party ” and collectively as the “ parties .”

<div align='center'>W I T N E S S E T H:</div>

WHEREAS, as of the date hereof, the Shareholder owns the number of common shares, par value $0.01 per share (the “ Parent Shares ”), of Maiden Holdings, Ltd., a Bermuda exempted company limited by shares (“ Parent ”), set forth on the Shareholder’s signature page hereto (such Parent Shares, together with any other Parent Shares over which the Shareholder acquires ownership (including (x) pursuant to Section 3.01(b) and Section 3.01(c) and (y) beneficial ownership (as defined in Rule 13d-3 of the Exchange Act, which meaning will apply for all purposes of this Agreement whenever the term “beneficial” or “beneficially” is used)) during the period from the date hereof through the termination of this Agreement, are collectively referred to herein as the “ Subject Shares ”);

WHEREAS, concurrently with the execution and delivery of this Agreement, the Company, all of the equityholders of the Company, Parent, Ranger U.S. Newco LLC, a Delaware limited liability company and a direct wholly owned Subsidiary of Parent (“ US NewCo ”), Ranger Bermuda Merger Sub Ltd, a Bermuda exempted company limited by shares and a direct wholly owned Subsidiary of US NewCo (“ Merger Sub Ltd. ”), Ranger Bermuda Topco Ltd, a Bermuda exempted company limited by shares and a direct wholly owned Subsidiary of Parent (“ Bermuda NewCo ”), and Ranger Merger Sub 2 LLC, a Delaware limited liability company and a direct wholly owned Subsidiary of Bermuda NewCo (“ Merger Sub LLC ”), are entering into a Combination Agreement (the “ Combination Agreement ”), pursuant to