0001628280-24-015065 Sample Contracts

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
Agreement and Plan of Merger • April 5th, 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”).

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TERM LOAN CREDIT AGREEMENT
Loan Credit Agreement • April 5th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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 • April 5th, 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.

MANAGEMENT CONSULTING AGREEMENT
Management Consulting Agreement • April 5th, 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 • April 5th, 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 • April 5th, 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
Agreement • April 5th, 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

AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023
Outsourcing Agreement • April 5th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

This First Amendment to the Amended and Restated Outsourcing Agreement (“Amendment”) is entered into effective 01 January, 2024 (the “First Amendment Effective Date”) by and among Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services, Inc., and Aspen Bermuda Limited (“Customer”), and Genpact (UK) Limited (“Supplier”); each of Customer and Supplier are a “Party” and collectively, the “Parties”.

FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT
Term Loan Credit Agreement • April 5th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

dated as of December 18, 2023, is among Aspen Insurance Holdings Limited (the “Borrower”), the several banks that are parties hereto, and Citibank, N.A., as administrative agent (in such capacity, the “Administrative Agent”). Capitalized terms used but not defined herein have the respective meanings set forth in the Credit Agreement (as defined below).

FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT
Credit Agreement • April 5th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance

This FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of January 6, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that are parties hereto, and Barclays Bank PLC, as administrative agent (in such capacity, the “Administrative Agent”). Capitalized terms used but not defined herein have the respective meanings set forth in the Credit Agreement (as defined below).

INDEMNIFICATION AGREEMENT
Indemnification Agreement • April 5th, 2024 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • England and Wales

THIS INDEMNIFICATION AGREEMENT (this “Agreement”) is made as of [insert month] [insert day], [insert year] (the “Effective Date”), by and between Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”) and ______________ (the “Indemnitee”).

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