Aspen Insurance Holdings LTD Sample Contracts

EXHIBIT 4.4 FIRST SUPPLEMENTAL INDENTURE
First Supplemental Indenture • October 14th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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Credit Agreement • November 25th, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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Credit Agreement • August 9th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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364-Day Credit Agreement • November 25th, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
EXHIBIT 4.5 ASPEN INSURANCE HOLDINGS LIMITED 6.00% SENIOR NOTES DUE 2014 EXCHANGE AND REGISTRATION RIGHTS AGREEMENT
Exchange and Registration Rights Agreement • October 14th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
EXHIBIT 1.1 ASPEN INSURANCE HOLDINGS LIMITED ORDINARY SHARES, PAR VALUE 0.15144558(CENTS) PER SHARE UNDERWRITING AGREEMENT
Underwriting Agreement • December 3rd, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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Service Agreement • September 24th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
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Subordinated Indenture • February 4th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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Service Agreement • March 14th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018
Merger Agreement • August 28th, 2018 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Delaware

This AGREEMENT AND PLAN OF MERGER (this “Agreement”) dated as of August 27, 2018, among Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”), Highlands Holdings, Ltd., a Bermuda exempted company (“Parent”), and Highlands Merger Sub, Ltd., a Bermuda exempted company and a wholly owned Subsidiary of Parent (“Merger Sub”).

TERM LOAN CREDIT AGREEMENT
Term Loan Credit Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
SERVICE AGREEMENT
Service Agreement • February 22nd, 2017 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENT
Restricted Share Unit Award Agreement • February 13th, 2019 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
CHANGE OF CONTROL EMPLOY MENT AGREEMENT
Change of Control Employment Agreement • April 29th, 2019 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

The Board of Directors of Holdings (the "Board") and the board of directors or the Company (the "Company Board") have determined that it is in the best interests of Holdings and the Company and its stockholders to assure that Holdings and the Company will have the continued dedication of the Executive, notwithstanding the possibility, threat or occurrence of a Change of Control (as defined below) of Holdings. The Board and the Company Board believe it is imperative to diminish the inevitable distraction of the Executive by virtue of the personal uncertainties and risks created by a pending or Threatened Change of Control and to encourage the Executive's full attention and dedication to Holdings and the Company currently and in the event of any threatened or pending Change of Control, and to provide the Executive with compensation and benefits arrangements upon a Change of Control that ensure that the compensation and benefits expectations of the executive will be satisfied and that are

Aspen Insurance Holdings Limited Class A Ordinary Shares Underwriting Agreement
Underwriting Agreement • April 29th, 2025 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

The shareholders of Aspen Insurance Holdings Limited, a Bermuda exempted company limited by shares (the “Company”), named in Schedule II hereto (the “Selling Shareholders”) propose, subject to the terms and conditions stated in this agreement (this “Agreement”), to sell to the Underwriters named in Schedule I hereto (the “Underwriters”) an aggregate of [ ò ] Class A ordinary shares, par value $0.001 per share (the “Ordinary Shares”), of the Company (the “Firm Shares”) and, at the election of the Underwriters, up to an additional [ ò ] Ordinary Shares (the “Optional Shares”). The Firm Shares and the Optional Shares that the Underwriters elect to purchase pursuant to Section 2 hereof are herein collectively called the “Shares.”

UNDERWRITING AGREEMENT
Underwriting Agreement • August 7th, 2019 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
EMPLOYMENT AGREEMENT
Employment Agreement • February 19th, 2016 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Connecticut

AGREEMENT (the “Agreement”), dated and entered into as of January 24, 2011, between Aspen Insurance U.S. Services Inc., a Delaware corporation, (the “Company”), and Emil Issavi (the “Executive”).

CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK...
Reinsurance Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

This AMENDED AND RESTATED REINSURANCE AGREEMENT, dated as of January 10, 2022 (this “Agreement”), is made by and among Aspen Insurance UK Limited, a company incorporated in England and Wales, Aspen Managing Agency Limited, a company incorporated in England and Wales, for and on behalf of the underwriting members(s) of Lloyd’s Syndicate 4711, Aspen Bermuda Limited, a company incorporated in Bermuda, Aspen American Insurance Company, a Texas-domiciled insurance company, Aspen Specialty Insurance Company, a North Dakota-domiciled insurance company (individually or collectively, “Aspen”), Aspen Insurance Holdings Limited, a company incorporated in Bermuda (“Aspen Parent”) (solely for the purposes of Sections 11.1, 13.2, 14.1, 16.3, 16.9, 16.12, 16.13 and 16.16) and Cavello Bay Reinsurance Limited, a Bermuda insurance company (the “Reinsurer”). Capitalized terms used but not otherwise defined herein have the respective meanings set forth in Section 1.1.

AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018
Merger Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Delaware

This AGREEMENT AND PLAN OF MERGER (this “Agreement”) dated as of August 27, 2018, among Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”), Highlands Holdings, Ltd., a Bermuda exempted company (“Parent”), and Highlands Merger Sub, Ltd., a Bermuda exempted company and a wholly owned Subsidiary of Parent (“Merger Sub”).

ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENT
Underwriting Agreement • May 14th, 2008 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
MANAGEMENT CONSULTING AGREEMENT
Management Consulting Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

MANAGEMENT CONSULTING AGREEMENT, dated March 28, 2019 (this “Agreement”), by and between ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the “Company”), and APOLLO MANAGEMENT HOLDINGS, L.P., a Delaware limited partnership (the “Service Provider”).

DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED and MARK CLOUTIER SERVICE AGREEMENT
Service Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

Clause Page 1. DEFINITIONS AND INTERPRETATION 1 2. APPOINTMENT 3 3. TERM 3 4. DUTIES 4 5. INSIDE INFORMATION 5 6. REMUNERATION 6 7. TRAVEL AND EXPENSES 7 8. PENSION 7 9. BENEFITS 7 10. HOLIDAYS AND HOLIDAY PAY 7 11. SICKNESS, ABSENCE, DISABILITY OR DEATH 8 12. CONFIDENTIAL INFORMATION 9 13. PROTECTION OF THE COMPANY’S BUSINESS INTERESTS 11 14. INTELLECTUAL PROPERTY RIGHTS 14 15. TERMINATION 16 16. GARDEN LEAVE 19 17. CHANGE IN CONTROL 20 18. EFFECT OF TERMINATION OF THIS AGREEMENT 20 19. APPOINTMENT OF ATTORNEY 20 20. AMALGAMATION, RECONSTRUCTION AND CHANGE OF DIRECTOR 21 21. DISCIPLINARY AND GRIEVANCE PROCEDURES 21

CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE...
Master Services Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

The Service Provider has agreed to supply and Aspen has agreed to accept the Services on the terms and conditions of this Agreement;

DATED 24 DECEMBER 2020
Outsourcing Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • England and Wales

PART A DEFINITIONS AND INTERPRETATION 6 1. DEFINITIONS 6 2. INTERPRETATION 7 PART B TERM AND SERVICE PROVISION 8 3. TERM 8 4. SERVICES 10 5. DELAY 14 6. ACCEPTANCE 15 7. NOT USED 16 8. GOVERNANCE, REPORTING AND PERFORMANCE 16 9. CHANGE CONTROL 18 PART C PERFORMANCE AND QUALITY 18 10. HOLDBACK, SERVICE LEVELS AND LIQUIDATED DAMAGES 18 11. SERVICE IMPROVEMENT AND ADVANCES IN TECHNOLOGY 19 12. REFERENCE 20 PART D OPERATION OF THE SERVICES 20 13. ASSETS 20 14. CO-OPERATION AND THIRD PARTY CONTRACTS 21 15. PERSONNEL 22 16. SERVICE LOCATIONS 24 17. SUBCONTRACTORS 25 18. DATA AND SECURITY REQUIREMENTS 26 19. BUSINESS CONTINUITY AND DISASTER RECOVERY 27 20. REGULATORY MATTERS AND AUDIT RIGHTS 28 21. CUSTOMER DEPENDENCIES 32 PART E PAYMENT 32 22. CHARGES 33 23. TAX 34 24. VALUE FOR MONEY/BENCHMARKING 34

DEPOSIT AGREEMENT Dated November 26, 2024 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING...
Deposit Agreement • December 11th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

DEPOSIT AGREEMENT, dated November 26, 2024 among ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the “Company”), COMPUTERSHARE INC., a Delaware corporation (“Computershare”), and its affiliate, COMPUTERSHARE TRUST COMPANY, N.A., a federally chartered trust company (the “Trust Company”), jointly as Depositary (as hereinafter defined), and the holders from time to time of Receipts (as hereinafter defined) issued hereunder.

PLEDGE AGREEMENT
Pledge Agreement • October 13th, 2006 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

PLEDGE AGREEMENT, dated as of 17 JANUARY 2006, (this ‘‘Agreement’’) made among Aspen Insurance Ltd, a company organized and existing under the laws of Bermuda (the ‘‘Pledgor’’), and Citibank, N.A. (the ‘‘Pledgee’’).