June 10, 2025

As Representatives of the several Underwriters named in Schedule I

c/o CITIGROUP GLOBAL MARKETS INC.

388 Greenwich Street

New York, NY 10013

c/o LLOYDS SECURITIES INC.

1095 Avenue of the Americas, 34th Floor

New York, NY 10036

c/o HSBC SECURITIES (USA) INC.

66 Hudson Boulevard

New York, NY 10001

1.    Introductory. Aspen Insurance Holdings Limited, an exempted company incorporated under the laws of Bermuda (the “Company”), proposes to issue and sell to the several underwriters (the “Underwriters”) named in Schedule I hereto for whom you are acting as representatives (the “Representatives”) $300,000,000 aggregate principal amount of its 5.750% Senior Notes due 2030 (the “Notes”). The respective principal amounts of the Notes to be so purchased by the several Underwriters are set forth opposite their names in Schedule I hereto.

The Notes are to be issued under an indenture (the “Original Indenture”), dated as of August 16, 2004, by and between the Company and Deutsche Bank Trust Company Americas, as trustee (the “Trustee”), as amended and supplemented by the Fifth Supplemental Indenture, to be dated on or around June 13, 2025 (together with the Original Indenture, the “Indenture”) between the Company and the Trustee.

To the extent there are no additional Underwriters listed on Schedule I other than you, the term Representatives as used herein shall mean you, as Underwriters, and the terms Representatives and Underwriters shall mean either the singular or plural as the context requires.

Any reference herein to the Registration Statement, the Base Prospectus, any Preliminary Prospectus Supplement or the Final Prospectus Supplement (each as defined below) shall be deemed to refer to and include the documents incorporated by reference therein pursuant to Item 6 of Form F-3 which were filed under the Securities Exchange Act of 1934, as amended, and the rules and regulations of the Securities and Exchange Commission (the “Commission”) promulgated thereunder (the “Exchange Act”) on or before the Effective Date (as defined below) of the Registration Statement or the issue date of the Base Prospectus, any Preliminary Prospectus Supplement or the Final Prospectus Supplement, as the case may be; and any reference herein to the terms “amend,” “amendment” or “supplement” with respect to the Registration Statement, the Base Prospectus, any Preliminary Prospectus Supplement or the Final Prospectus Supplement shall be deemed to refer to and include the filing of any document under the Exchange Act after the Effective Date of the Registration Statement or the issue date of the Base Prospectus, any Preliminary Prospectus Supplement or the Final Prospectus Supplement, as the case may be, deemed to be incorporated therein by reference.

The Company hereby agrees, pursuant to this underwriting agreement (the “Agreement”), with the Underwriters as follows:

2.    Representations, Warranties and Agreements of the Company.

(a)    The Company represents and warrants to, and agrees with, the several Underwriters that:

(i)    The Company meets the requirements for use of Form F-3 under the Securities Act of 1933, as amended, and the rules and regulations of the Commission promulgated thereunder (the “Act”) and has prepared and filed with the Commission a shelf registration statement on Form F-3 (file number 333-272650), including a related base prospectus, for registration under the Act of the offering and sale of the Notes and such shelf registration statement has been declared effective. The Company may have filed one or more amendments thereto, including a Preliminary Prospectus Supplement and a Base Prospectus, each of which has previously been furnished to you and has become effective upon filing. The Company will file with the Commission a Final Prospectus Supplement relating to the Notes in accordance with Rule 424(b) under the Act. The Registration Statement, at the Execution Time, is effective and meets the requirements set forth in Rule 415(a)(1)(x) under the Act.

“Base Prospectus” shall mean the prospectus referred to in this paragraph 2(a)(i) deemed to be part of the Registration Statement at the Effective Date.

“Effective Date” shall mean each date and time that the Registration Statement and any post-effective amendment or amendments thereto became or become effective.

“Execution Time” shall mean the date and time that this Agreement is executed and delivered by the parties hereto.

“Final Prospectus Supplement” shall mean the prospectus supplement relating to the Notes that was first filed pursuant to Rule 424(b) under the Act after the Execution Time, together with the Base Prospectus.

“Preliminary Prospectus Supplement” shall mean any preliminary prospectus supplement to the Base Prospectus which describes the Notes and the offering thereof and is used prior to filing of the Final Prospectus Supplement, together with the Base Prospectus.

“Registration Statement” shall mean the registration statement referred to in this paragraph 2(a)(i), including exhibits and financial statements, as amended on each Effective Date and, in the event any post-effective amendment thereto becomes effective prior to the Closing Date, shall also mean such registration statement as so amended.

(ii)    On each Effective Date, the Registration Statement did, and when the Final Prospectus Supplement is first filed in accordance with Rule 424(b) under the Act and on the Closing Date (as defined herein), the Final Prospectus Supplement (and any amendment or supplement thereto) will, comply in all material respects with the applicable requirements of the Act, the Exchange Act and the Trust Indenture Act of 1939, as amended, and the rules and regulations of the Commission promulgated thereunder (the “Trust Indenture Act”); on each Effective Date and at the Execution Time, the Registration Statement did not and will not contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary in order to make the statements therein not misleading; on each Effective Date and on the Closing Date, the Indenture did or will comply in all material respects with the applicable requirements of the Trust Indenture Act and the rules thereunder; and on the date of any filing pursuant to Rule 424(b) under the Act and on the Closing Date, the Final Prospectus Supplement (together with any amendment or supplement thereto) will not include any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading; provided, however, that the Company makes no representations or warranties as to (i) that part of the Registration Statement which shall constitute the Statement of Eligibility and Qualification (Form T-1) under the Trust Indenture Act of the Trustee or (ii) the information contained in or omitted from the Registration Statement or the Final Prospectus Supplement (or any amendment or supplement thereto) in reliance upon and in conformity with information furnished in writing to the Company by or on behalf of any Underwriter through the Representatives specifically for inclusion in the Registration Statement or the Final Prospectus Supplement (or any amendment or supplement thereto), it being understood and agreed that the only such information furnished by or on behalf of any Underwriter consists of the information described as such in Section 8(e) hereof.

(iii)    As of the Applicable Time (as defined below), the Disclosure Package (as defined below), when taken together as a whole, does not contain any untrue statement of a material fact or omit to state any material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading. The preceding sentence does not apply to statements in or omissions from the Disclosure

Package based upon and in conformity with written information furnished to the Company by or on behalf of any Underwriter through the Representatives specifically for use therein, it being understood and agreed that the only such information furnished by or on behalf of any Underwriter consists of the information described as such in Section 8(e) hereof.

The “Applicable Time” shall mean 2:15 p.m. (New York City time) on the date of this Agreement.

The “Disclosure Package” shall mean (i) the Preliminary Prospectus Supplement, as amended and supplemented to the Applicable Time, (ii) the Issuer Free Writing Prospectuses, if any, identified in Schedule III hereto, (iii) the Final Term Sheet (as defined below) and (iv) any other Free Writing Prospectus that the parties hereto shall hereafter expressly agree in writing to treat as part of the Disclosure Package.

“Free Writing Prospectus” shall mean a free writing prospectus, as defined in Rule 405 under the Act.

“Issuer Free Writing Prospectus” shall mean an issuer free writing prospectus, as defined in Rule 433 under the Act.

(iv)    (A) At the earliest time after the filing of the Registration Statement that the Company or another offering participant made a bona fide offer (within the meaning of Rule 164(h)(2) under the Act) of the Notes and (B) as of the Execution Time (with such date being used as the determination date for purposes of this clause (B)), the Company was not and is not an Ineligible Issuer (as defined in Rule 405 under the Act), without taking account of any determination by the Commission pursuant to Rule 405 that it is not necessary that the Company be considered an Ineligible Issuer.

(v)    Each Issuer Free Writing Prospectus and the final term sheet, substantially in the form of Schedule II hereto (the “Final Term Sheet”), will not include any information that conflicts in any material respect with the information contained in the Registration Statement, including any document incorporated by reference therein and any prospectus supplement deemed to be a part thereof that has not been superseded or modified. The foregoing sentence does not apply to statements in or omissions from any Issuer Free Writing Prospectus based upon and in conformity with written information furnished to the Company by any Underwriter through the Representatives specifically for use therein, it being understood and agreed that the only such information furnished by or on behalf of any Underwriter consists of the information described as such in Section 8(e) hereof.

(vi)    The Company is a “foreign private issuer,” as such term is defined in Rule 405 under the Act.

(vii) Since the respective dates as of which information is given in the Disclosure Package and the Final Prospectus Supplement, there has not been any material adverse change in the authorized or issued share capital, the capital or surplus or long term debt of the Company or any of its subsidiaries or any material adverse change, or any development involving a prospective material adverse change, in or affecting the general affairs, management, financial position, shareholders’ equity or results of operations of the Company and its subsidiaries, otherwise than as set forth or contemplated in the Disclosure Package and the Final Prospectus Supplement. There is no contract or document required to be described in the Registration Statement, the Disclosure Package or the Final Prospectus Supplement or to be filed as an exhibit to the Registration Statement which is not described or filed as required.

(viii)    Neither the Company nor any of Aspen Insurance UK Limited (“Aspen U.K.”), Aspen Bermuda Limited (“Aspen Bermuda”) or Aspen American Insurance Company (“AAIC” and, together with Aspen U.K. and Aspen Bermuda, the “Designated Subsidiaries”) hold direct title to any real property; all of the leases, subleases and licenses under which the Company or any of its Designated Subsidiaries holds real properties described in the Disclosure Package and the Final Prospectus Supplement are in full force and effect, and neither the Company nor any Designated Subsidiary has any notice of any claim of any sort that has been asserted by anyone adverse to the rights of the Company or any Designated Subsidiary under any of the leases, subleases or licenses mentioned above, or affecting or questioning the rights of the Company or such Designated Subsidiary to the continued possession of the leased, subleased or licensed premises under any such lease or sublease, except where the failure to have such leases in full force and effect or the failure to have any such notice of any such claim would not, individually or in the aggregate, result in a material adverse change in the condition, financial or otherwise, or in the earnings, results of operations, business affairs, shareholders’ equity or business prospects of the Company and its subsidiaries, taken as a whole (a “Material Adverse Effect”).

(ix)    The Company has been duly incorporated and is validly existing as an exempted company in good standing under the laws of Bermuda, with power and authority (corporate and other) to own its properties and conduct its business as described in the Disclosure Package and the Final Prospectus Supplement, and has been duly qualified as a foreign corporation for the transaction of business and is in good standing under the laws of each other jurisdiction in which it owns or leases properties or conducts any business so as to require such qualification, except where the failure to so qualify or be in good standing would not result in a Material Adverse Effect; each of the Designated Subsidiaries has been duly organized or incorporated and is validly existing as a company or corporation in good standing (including, in the case of Aspen Bermuda, as an exempted company) under the laws of its jurisdiction of organization or incorporation, with power and authority (corporate and other) to own its properties and conduct its business as described in the Disclosure Package and the Final Prospectus Supplement, and has been duly qualified as a foreign company or corporation for the transaction of business and is in good standing under the laws of each other jurisdiction in which it owns or leases properties or conducts any business so as to require such qualification, except where the failure to so qualify or be in good standing would not result in a Material Adverse Effect; and none of the Company’s subsidiaries, other than Aspen U.K., Aspen Bermuda, Aspen (UK) Holdings Limited, AAIC, Aspen Specialty Insurance Company and Aspen Underwriting Limited, is a “Significant Subsidiary” (as defined in Rule 1-02(w) of Regulation S-X under the Act) of the Company.

(x)    The Company has an authorized share capital as set forth in the Disclosure Package and the Final Prospectus Supplement and all of the issued shares of the Company have been duly and validly authorized and issued and are fully paid and non-assessable; and all of the issued shares of each Designated Subsidiary of the Company have been duly and validly authorized and issued, are fully paid and nonassessable and, except as set forth in the Disclosure Package and the Final Prospectus Supplement, are owned directly or indirectly by the Company, free and clear of all liens, encumbrances, equities or claims.

(xi)    This Agreement has been duly authorized, executed and delivered by the Company and constitutes the valid and binding agreement of the Company.

(xii)    The Indenture has been duly authorized by the Company and, assuming due authorization, execution and delivery by the Trustee, when executed and delivered by the Company, will constitute a legal, valid and binding instrument enforceable against the Company in accordance with its terms, except as the enforceability thereof may be limited by bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium or similar laws relating to or affecting creditors’ rights generally and by general equitable principles (regardless of whether such enforceability is considered in a proceeding in equity or at law). The Indenture will conform to the description thereof in the Disclosure Package and the Final Prospectus Supplement.

(xiii)    The Notes have been duly authorized by the Company and, when executed by the Company and authenticated by the Trustee in accordance with the Indenture and delivered to the Underwriters against payment therefore in accordance with the terms of this Agreement, will be validly issued and delivered, and will constitute valid and binding obligations of the Company entitled to the benefits of the Indenture and enforceable against the Company in accordance with their terms, except as enforcement thereof may be limited by bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium or other similar laws relating to or affecting the enforcement of creditors’ rights generally and by general equitable principles (regardless of whether such enforceability is considered in a proceeding in equity or at law), and the Notes conform, or will conform, to the description thereof in the Disclosure Package and the Final Prospectus Supplement.

(xiv) There are no currency exchange control laws in Bermuda (or any political subdivision or taxing authority thereof), that would be applicable to the payment of any amounts (A) under the Notes by the Company (other than as may apply to residents of Bermuda for Bermuda exchange control purposes) or (B) by any of the Company’s subsidiaries to the Company; the Bermuda Monetary Authority (the “BMA”) has designated the Company and Aspen Bermuda as non-resident for exchange control purposes and has granted the Company permission for the issue and free transferability of the Notes pursuant to the Registration Statement, to and among persons who are non-residents of Bermuda for exchange control purposes (including permission for the issue and free transferability of up to 20% of the Notes to and among persons who are residents of Bermuda for exchange control purposes); such permission has not been revoked and is in full force and effect, and the Company has no knowledge of any proceedings planned or threatened for the revocation of such permission; the Company and Aspen Bermuda are “exempted companies” under Bermuda law and have not (V) acquired and do not hold any land for their respective business in Bermuda, other than that held by way of lease or tenancy for terms of not more than 50 years, without the express authorization of the Bermuda Minister of Finance, (W) acquired and do not hold land by way of lease or tenancy for terms of not more than 21 years in order to provide accommodation or recreational facilities for their officers and employees, without the express authority of the Bermuda Minister of Finance, (X) taken mortgages on land in Bermuda to secure an amount in excess of $50,000, without the consent of the Bermuda Minister of Finance, (Y) acquired any bonds or debentures secured by any land in Bermuda, except bonds or debentures issued by the government of Bermuda or a public authority of Bermuda, or (Z) conducted their business in a manner that is prohibited for “exempted companies” under Bermuda law; neither the Company nor Aspen Bermuda has received notification from the BMA or any other Bermuda governmental authority of proceedings relating to the modification or revocation of its designation as non-resident for exchange control purposes, its status as an “exempted company” or permission to the Company to issue and transfer the Notes.

(xv)    The execution, delivery and performance of this Agreement and the consummation of the transactions herein contemplated and the fulfilment of the terms hereof (including, without limitation, the issuance and sale of the Notes to the Underwriters) will not conflict with or result in a breach or violation of any of the terms or provisions of, or constitute a default under, (A) the certificate of incorporation, memorandum of association, articles of association, bye-laws, by-laws or other organizational document, as amended (any such document, a “Constitutional Document”), as the case may be, of the Company or any of its subsidiaries, (B) any indenture, mortgage, deed of trust, loan agreement or other agreement or instrument to which the Company or any of its subsidiaries is a party or by which the Company or any of its subsidiaries is bound or to which any of the property or assets of the Company or any of its subsidiaries is subject, or (C) any statute or any order, rule or regulation of any court or governmental agency or body, any stock exchange authority or any other regulatory authority (hereinafter referred to as a “Governmental Agency”) having jurisdiction over the Company or any of its subsidiaries or any of their properties, except, in the case of the foregoing clauses (B) and (C), as would not, individually or in the aggregate, result in a Material Adverse Effect or have a material adverse effect on the transactions contemplated hereby.

(xvi) No consent, approval, authorization, order, registration or qualification of or with any Governmental Agency (hereinafter referred to as the “Governmental Authorizations”) is required for the sale and issuance of the Notes or the consummation by the Company of the transactions contemplated hereby, except (A) the registration of the Notes under the Act, (B) such Governmental Authorizations as have been duly obtained and are in full force and effect and copies of which have been furnished to the Representatives, (C) such Governmental Authorizations as may be required under state securities laws, Blue Sky laws, insurance securities laws, any laws of jurisdictions outside the United States or the bylaws and rules of the Financial Industry Regulatory Authority, Inc. in connection with the purchase and distribution of the Notes by or for the respective accounts of the Underwriters and (D) such consents, approvals, authorizations, registrations or qualifications as may be required and have been obtained from the BMA and provided in each case that any written instrument of transfer effecting the sale and delivery of the Notes hereunder is executed and retained outside of the United Kingdom.

(xvii)    Neither the Company nor any of the Designated Subsidiaries is (A) in violation of any of its Constitutional Documents or (B) in default in the performance or observance of any obligation, agreement, covenant or condition contained in any indenture, mortgage, deed of trust, loan agreement, lease or other agreement, or instrument to which it is a party or by which it or any of its properties may be bound, except, in the case of clause (B), for any such defaults or violations that would not, individually or in the aggregate, result in a Material Adverse Effect or as otherwise waived or consented to by the parties or shareholders to which the Company or the Designated Subsidiaries owes any obligations under such agreements or documents.

(xviii)    No stamp or other issuance or transfer taxes or duties and no capital gains, income, withholding or other taxes are payable by or on behalf of any Underwriter to Bermuda or any political subdivision or taxing authority thereof or therein in connection with (A) the sale and delivery of the Notes to or for the respective accounts of the Underwriters or (B) the sale and delivery outside Bermuda by the Underwriters of the Notes to the Underwriters thereof.

(xix)    Except as disclosed in the Disclosure Package and the Final Prospectus Supplement, the Company has no knowledge of any threatened or pending downgrading of the rating accorded to the securities of the Company or the financial strength or claims-paying ability of the Company or any of the Designated Subsidiaries, as the case may be, by A.M. Best Company, Inc. (“A.M. Best”), Standard & Poor’s Ratings Services, a division of S&P Global Inc. (“S&P”), or Moody’s Investors Service, Inc. (“Moody’s” and, collectively with A.M. Best and S&P, the “Ratings Agencies” and, individually, a “Rating Agency”). To the best of the Company’s knowledge, the Ratings Agencies are the only “nationally recognized statistical rating organizations,” as that term is defined in Section 3(a)(62) of the Exchange Act, that currently rate the securities of the Company or the financial strength or claims-paying ability of the Company or any of the Designated Subsidiaries.

(xx)    Except as disclosed in the Disclosure Package and the Final Prospectus Supplement, there are no legal or governmental proceedings pending to which the Company or any of its subsidiaries is a party or of which any property of the Company or any of its subsidiaries is the subject which, if determined adversely to the Company or any of its subsidiaries, would, individually or in the aggregate, result in a Material Adverse Effect; and, to the Company’s knowledge, no such proceedings are threatened or contemplated by any Governmental Agency or threatened by others.

(xxi)    The Company is not and, after giving effect to the offering and sale of the Notes and the application of the net proceeds from such sale as described in the Disclosure Package and the Final Prospectus Supplement, will not be an “investment company” as defined in the Investment Company Act of 1940, as amended.

(xxii)    Except as disclosed in the Disclosure Package and the Final Prospectus Supplement, each of the Designated Subsidiaries that is an insurance brokerage company, insurer or reinsurer, as the case may be, is duly licensed under the insurance laws and the rules, regulations and interpretations of the insurance regulatory authorities thereunder (collectively, “Insurance Laws”) of each jurisdiction in which the conduct of its existing business as described in the Disclosure Package and the Final Prospectus Supplement requires such licensing, except for such jurisdictions in which the failure to be so licensed would not, individually or in the aggregate, result in a Material Adverse Effect; each of the Company and the Designated Subsidiaries has made all required filings under applicable holding company statutes or other Insurance Laws in each jurisdiction where such filings are required, except for such jurisdictions in which the failure to make such filings would not, individually or in the aggregate, result in a Material Adverse Effect; each of the Company and the Designated Subsidiaries has all other necessary authorizations, approvals, orders, consents, certificates, licenses, permits, registrations and qualifications of and from all insurance regulatory authorities necessary to conduct their respective existing businesses as described in the Disclosure Package and the Final Prospectus Supplement and all of the foregoing are in full force and effect, except where the failure to have such authorizations, approvals, orders, consents, certificates, licenses, permits, registrations or qualifications or their failure to be in full force and effect would not, individually or in the aggregate, result in a Material Adverse Effect; none of the Company or the Designated Subsidiaries has received any notification from any insurance regulatory authority or other governmental authority in the United States, Bermuda, the United Kingdom or elsewhere to the effect that any additional authorization, approval, order, consent, certificate, permit, registration or qualification is needed to be obtained by either the Company or the Designated Subsidiaries to conduct its existing business as described in the Disclosure Package and the Final Prospectus Supplement, except for any such notification received where the failure to obtain such additional authorization, approval, order, consent, certificate, permit, registration or qualification would not, individually or in the aggregate, result in a Material Adverse Effect; and except as otherwise described in the Disclosure Package and the Final Prospectus Supplement, no insurance regulatory authority has issued any order or decree impairing, restricting or prohibiting the payment of dividends by the Company or any of the Designated Subsidiaries.

(xxiii)    Each of the Company and the Designated Subsidiaries, taken as a whole, maintain a system of internal accounting controls that is designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles.

(xxiv) Each of the Company and the Designated Subsidiaries has filed all statutory financial returns, reports, documents and other information required to be filed pursuant to the applicable Insurance Laws of the United States and the various states thereof, Bermuda, the United Kingdom and each other jurisdiction applicable thereto, except where the failure, individually or in the aggregate, to file such return, report, document or information would not result in a Material Adverse Effect; and each of the Company and the Designated Subsidiaries maintains its books and records in accordance with, and is otherwise in compliance with, the applicable Insurance Laws of the United States and the various states thereof, Bermuda, the United Kingdom and each other jurisdiction applicable thereto, except where the failure to so maintain its books and records or be in compliance would not, individually or in the aggregate, result in a Material Adverse Effect.

(xxv)    (A) From February 15, 2019, any tax returns required to be filed by the Company or any of its current subsidiaries, other than Aspen Specialty Insurance Company, Aspen U.K. and Aspen Insurance UK Services Limited (the “Excluded Subsidiaries”), in any jurisdiction have been accurately prepared and timely filed (taking into account any valid extensions that have been obtained), and any taxes, including any withholding taxes, excise taxes, franchise taxes and similar fees, sales taxes, use taxes, penalties and interest, assessments and fees and other charges due or claimed to be due from such entities have been paid, other than any of those being contested in good faith and for which adequate reserves have been provided or any of those currently payable without penalty or interest and (B) to the Company’s knowledge, any tax returns required to be filed by any Excluded Subsidiary in any jurisdiction have been accurately prepared and timely filed and any taxes, including any withholding taxes, excise taxes, franchise taxes and similar fees, sales taxes, use taxes, penalties and interest, assessments and fees and other charges due or claimed to be due from an Excluded Subsidiary have been paid, other than any of those being contested in good faith and for which adequate reserves have been provided or any of those currently payable without penalty or interest, in either case with respect to the foregoing clauses (A) and (B), (1) except to the extent that the failure to so file or pay would not result in a Material Adverse Effect and (2) other than those tax returns that would be required to be filed or taxes that would be payable by the Company or any of its current subsidiaries if (a) any of them that is treated as a U.S. corporation was characterized as a “personal holding company” as defined in Section 542 of the U.S. Internal Revenue Code of 1986, as amended (the “Code”), (b) any of them other than Aspen Specialty Insurance Management, Inc., Aspen Specialty Insurance Company, Aspen U.S. Holdings, Inc., Aspen Insurance U.S. Services Inc., Aspen Re America, Inc., Aspen Specialty Insurance Solutions LLC and AAIC (collectively, the “U.S. Subsidiaries”), Aspen U.K. and Aspen Underwriting Limited was characterized as engaged in a U.S. trade or business, and (c) any of them other than Aspen U.K., Aspen (UK) Holdings Limited, Aspen Insurance UK Services Limited, Aspen Managing Agency Limited, Aspen Underwriting Limited, Aspen Risk Management Limited, Aspen (US) Holdings Limited, Aspen UK Syndicate Services Limited (formerly APJ Services Limited) and Aspen European Holdings (collectively, the “U.K. Subsidiaries”) was characterized as resident, managed and controlled or carrying on a trade through a permanent establishment, branch or agency in the United Kingdom for United Kingdom tax purposes; no deficiency assessment with respect to a proposed adjustment of the Company’s or any of its subsidiaries’ taxes is pending or, to the best of the Company’s knowledge, threatened; and there is no tax lien, whether imposed by any federal, state, or other taxing authority, outstanding against the assets, properties or business of the Company or any of its subsidiaries, in either case, which would have a Material Adverse Effect.

(xxvi)    Each of the Company and Aspen Bermuda have received from the Bermuda Minister of Finance an assurance under the Exempted Undertakings Tax Protection Act 1966, as amended, of Bermuda that in the event that Bermuda enacts legislation imposing tax computed on profits, income, any capital asset, gain or appreciation, or any tax in the nature of estate duty or inheritance, other than any tax imposed in consequence of the Corporate Income Tax Act 2023, then the imposition of any such tax shall not be applicable to the Company and Aspen Bermuda or to any of their operations or their shares, debentures or other obligations, until March 31, 2035, and the Company has not received any notification to the effect that such assurance may be revoked or otherwise not honored by the Bermuda government.

(xxvii)    Although the question of whether a non-United Kingdom incorporated company is resident in the United Kingdom or carrying on a trade through a permanent establishment in the United Kingdom is an inherently factual issue, subject to considerable uncertainty, and there is no assurance that His Majesty’s Revenue and Customs could not successfully assert otherwise, the Company does not believe that either the Company or any of its current subsidiaries (except for the U.K. Subsidiaries) currently should be, or upon the sale of the Notes contemplated hereby should be, characterized as resident or carrying on a trade through a permanent establishment in the United Kingdom.

(xxviii)     Although the question of whether a trade or business is conducted in the United States by a non-U.S. corporation is inherently a factual issue, subject to considerable uncertainty, and there is no assurance that the Internal Revenue Service could not successfully assert otherwise, the Company believes that, except for the U.S. Subsidiaries, Aspen U.K. and Aspen Underwriting Limited, neither the Company nor any of its subsidiaries currently should be, or upon the sale of the Notes contemplated hereby should be, considered to be engaged in a trade or business within the United States for purposes of Section 864(b) of the Code. The Company believes that the Company should not be characterized as a “passive foreign investment company” as defined in Section 1297 of the Code for the current year or the foreseeable future. Aspen U.K. and Aspen Bermuda intend to operate in a manner that is intended to ensure that either or both (i) the “related person insurance income” (as defined in Section 953 of the Code) of either Aspen U.K. or Aspen Bermuda does not equal or exceed 20% of each such company’s gross insurance income for any taxable year in the foreseeable future, or (ii) less than 20% of the total combined voting power of all classes of stock of each of Aspen U.K. and Aspen Bermuda entitled to vote and less than 20% of the total value of each of Aspen U.K. and Aspen Bermuda is owned (directly or indirectly) by persons who are (directly or indirectly) insured under any policy of insurance or reinsurance issued by Aspen U.K. or Aspen Bermuda, as applicable, or who are related persons to any such person for any taxable year in the foreseeable future.

(xxix) The audited consolidated financial statements included or incorporated by reference in the Disclosure Package and the Final Prospectus Supplement, together with the related schedules and notes, present fairly, in all material respects, the financial position of the Company and its consolidated subsidiaries at the dates indicated and the statement of operations, shareholders’ equity and cash flows of the Company and its consolidated subsidiaries for the periods specified; except as otherwise disclosed in the Disclosure Package and the Final Prospectus Supplement, said consolidated financial statements have been prepared in conformity with generally accepted accounting principles in the United States (“U.S. GAAP”) applied on a consistent basis throughout the periods involved; the supporting schedules included or incorporated by reference in the Disclosure Package and the Final Prospectus Supplement present fairly, in all material respects, in accordance with U.S. GAAP, the information required to be stated therein; and the selected financial data and the summary financial information included or incorporated by reference in the Disclosure Package and the Final Prospectus Supplement, if any, present fairly, in all material respects, the information shown therein and have been compiled on a basis consistent with that of the audited financial statements included or incorporated by reference in the Disclosure Package and the Final Prospectus Supplement.

(xxx)     Each of Ernst & Young LLP and Ernst & Young Ltd., who have audited certain financial statements of the Company and its subsidiaries, is an independent public accountant as required by the Act.

(xxxi)    The Company is subject to the reporting requirements of either Section 13 or Section 15(d) of the Exchange Act as a “Foreign Private Issuer” and files reports with the Commission on the Electronic Data Gathering, Analysis, and Retrieval (EDGAR) system. Any documents filed with or furnished to the Commission under the Exchange Act, when they were or are filed with or furnished to the Commission, (A) conformed or will conform in all material respects to the applicable requirements of the Exchange Act and (B) did not or will not, as of their respective dates, contain an untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading.

(xxxii)     The Company and its Designated Subsidiaries, taken as a whole, maintain disclosure controls and procedures (as such term is defined in Rule 13a-15(e) under the Exchange Act); such disclosure controls and procedures have been designed to ensure that material information relating to the Company and its subsidiaries is (x) made known to the Company’s principal executive officer and principal financial officer by others within those entities, and (y) accurate and complete in all material respects, fairly present the Company’s and its subsidiaries’ financial condition and results of operations, are made on a timely basis, and in a form required by applicable laws and stock exchange requirements.

(xxxiii)     No action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving the Company or any of its subsidiaries or its or their property is pending or, to the best knowledge of the Company, threatened that could reasonably be expected, individually or in the aggregate, to have a Material Adverse Effect, except as set forth in the Disclosure Package and the Final Prospectus Supplement (exclusive of any amendment or supplement thereto made after the date of this Agreement).

(xxxiv)     Neither the Company nor any of its subsidiaries nor, to the knowledge of the Company, any director, officer, agent, employee or other person acting on behalf of the Company or any of its subsidiaries has: (i) made any unlawful contribution, gift or other unlawful expense relating to political activity; (ii) made any direct or indirect bribe, kickback, rebate, payoff, influence payment or otherwise unlawfully provided anything of value to any “foreign official” (as defined in the U.S. Foreign Corrupt Practices Act of 1977, as amended (the “FCPA”)) or domestic government official; or (iii) taken any other action, directly or indirectly, that could result in a violation or a sanction for violation by such persons of the FCPA, the OECD Convention on Combating Bribery of Foreign Public Officials in International Business Transactions, the U.K. Bribery Act 2010 or the Bribery Act 2016 of Bermuda, each as may be amended, or similar law of any other relevant jurisdiction, or the rules or regulations thereunder; and the Company and its subsidiaries have instituted and maintain policies and procedures designed to ensure compliance therewith. No part of the proceeds of the offering will be used, directly or, to the knowledge of the Company, indirectly, in violation of the FCPA, the OECD Convention on Combating Bribery of Foreign Public Officials in International Business Transactions, the U.K. Bribery Act 2010 or the Bribery Act 2016 of Bermuda, each as may be amended, or similar law of any other relevant jurisdiction, or the rules or regulations thereunder.

(xxxv)    The operations of the Company and its subsidiaries are and have been conducted at all times in compliance with all applicable financial recordkeeping and reporting requirements and the money laundering statutes of all jurisdictions where the Company or any of its subsidiaries conducts business and the rules and regulations thereunder and any related or similar rules, regulations or guidelines, issued, administered or enforced by any governmental agency, including the Currency and Foreign Transactions Reporting Act of 1970, as amended (collectively, the “Money Laundering Laws”), and no action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving the Company or any of its subsidiaries with respect to the Money Laundering Laws is pending or, to the best knowledge of the Company, threatened.

(xxxvi) None of the Company nor any of its subsidiaries nor, to the knowledge of the Company, any director, officer, agent or employee of the Company or any of its subsidiaries (i) is, or is controlled or 50% or more owned in the aggregate by or is acting on behalf of, one or more individuals or entities that are currently the subject of any sanctions administered or enforced by the United States (including any administered or enforced by the Office of Foreign Assets Control of the U.S. Department of the Treasury, the U.S. Department of State or the Bureau of Industry and Security of the U.S. Department of Commerce), the United Nations Security Council, the European Union, a member state of the European Union (including sanctions administered or enforced by His Majesty’s Treasury of the United Kingdom) or other relevant sanctions authority (collectively, “Sanctions” and such persons, “Sanctioned Persons” and each such person, a “Sanctioned Person”), (ii) is located, organized or resident in a country or territory that is, or whose government is, the subject or target of Sanctions, including, without limitation, Crimea, Cuba, Iran, North Korea, Russia, Belarus, the so-called People’s Republic of Luhansk, the so-called People’s Republic of Donetsk or non-Ukrainian government controlled areas of Kherson and Zaporizhzhia (collectively, “Sanctioned Countries” and each, a “Sanctioned Country”) or (iii) will, directly or, to the knowledge of the Company, indirectly, use the proceeds of this offering, or lend, contribute or otherwise make available such proceeds to any subsidiary, joint venture partner or other individual or entity in any manner that would result in a violation of any Sanctions by, or could result in the imposition of Sanctions against, any individual or entity (including any individual or entity participating in the offering, whether as underwriter, advisor, investor or otherwise). Neither the Company nor any of its subsidiaries has engaged in any dealings or transactions prohibited by the Sanctions since April 24, 2019, nor does the Company or any of its subsidiaries have any plans to engage in dealings or transactions with or for the benefit of a Sanctioned Person, or with or in a Sanctioned Country in violation with applicable sanction laws.

(xxxvii)    The interactive data in eXtensible Business Reporting Language included or incorporated by reference in the Disclosure Package and the Final Prospectus Supplement fairly presents the information called for in all material respects and is prepared in accordance with the Commission’s rules and guidelines applicable thereto.

(xxxviii)    Except as would not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect, the Company and its Designated Subsidiaries’ information technology assets and equipment, computers, systems, networks, hardware, software, websites, applications, and databases (collectively, “IT Systems”) are adequate for, and operate and perform in all material respects as required in connection with the operation of the business of the Company and its Designated Subsidiaries as currently conducted, to the Company’s knowledge, free and clear of all material bugs, errors, defects, Trojan horses, time bombs, malware and other corruptants. Except as would not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect, the Company and its Designated Subsidiaries have implemented and maintained commercially reasonable controls, policies, procedures, and safeguards to maintain and protect their material confidential information and the integrity, continuous operation, redundancy and security of all IT Systems and data (including all “personal data” as defined by the EU General Data Protection Regulations (GDPR) (EU 2016 679) and any personal, personally identifiable, household, sensitive, confidential or regulated data (“Personal Data”)) used in connection with their businesses reasonably consistent with industry standards and practices, or as required by applicable regulatory standards, and there have been no breaches, violations, outages or unauthorized uses of or accesses to same, except for those that have been remedied without any loss of data, material cost or liability or the duty to notify any other person. Except as would not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect, the Company and its Designated Subsidiaries are presently in compliance with all applicable laws or statutes and all judgments, orders, rules and regulations of any court or arbitrator or governmental or regulatory authority, internal policies and contractual obligations relating to the privacy and security of IT Systems and Personal Data and to the protection of such IT Systems and Personal Data from unauthorized use, access, misappropriation or modification.

3.    Purchase, Sale and Delivery of the Notes.

(a)    On the basis of the representations, warranties and agreements herein contained, but subject to the terms and conditions herein set forth, the Company agrees to sell to the Underwriters, and the Underwriters agree, severally and not jointly, to purchase the Notes in the respective principal amounts set forth opposite such Underwriter’s name on Schedule I hereto from the Company at 99.270% of their principal amount. The Notes to be purchased by the Underwriters hereunder will be represented by one or more global certificates in book-entry form which will be deposited by or on behalf of the Company with The Depository Trust Company (“DTC”). Such global certificate or certificates representing the Notes shall be in such denomination or denominations and registered in such name or names as the Underwriters request upon notice to the Company at least 36 hours prior to the Closing Date, and shall be delivered by or on behalf of the Company to the Underwriters, against payment by or on behalf of the Underwriters of the purchase price therefor by wire transfer (same day funds), to such account or accounts as the Company shall specify prior to the Closing Date, or by such means as the parties hereto shall agree prior to the Closing Date. Such delivery of and payment for the Notes shall be made at the offices of Cleary Gottlieb Steen & Hamilton LLP, One Liberty Plaza, New York, New York at 10:00 A.M., New York time, on June 13, 2025, or at such other place, time or date as the Representatives, on the one hand, and the Company, on the other hand, may agree upon, such time and date of delivery against payment being herein referred to as the “Closing Date.” The Company will make such global certificate or certificates representing the Notes available for checking by the Underwriters at least 24 hours prior to the Closing Date.

4.    Offering by Underwriters. It is understood that the several Underwriters propose to offer the Notes for sale to the public as set forth in the Final Prospectus Supplement.

5.    Certain Agreements of the Company and the Underwriters.

(a)    The Company agrees with the Underwriters:

(i) Prior to the termination of the offering of the Notes, the Company will not file any amendment of the Registration Statement or supplement (including the Final Prospectus Supplement or any Preliminary Prospectus Supplement) to the Base Prospectus unless the Company has furnished you a copy for your review prior to filing and will not file any such proposed amendment or supplement to which you reasonably object. Subject to the foregoing sentence, the Company will cause the Final Prospectus Supplement, properly completed, and any amendment or supplement thereto to be filed in a form approved by the Representatives with the Commission pursuant to the applicable paragraph of Rule 424(b) under the Act within the time period prescribed and will provide evidence satisfactory to the Representatives of such timely filing. The Company will promptly advise the Representatives (1) when the Final Prospectus Supplement, and any amendment or supplement thereto, shall have been filed (if required) with the Commission pursuant to Rule 424(b), (2) when, prior to termination of the offering of the Notes, any amendment to the Registration Statement shall have been filed or become effective, (3) of any request by the Commission or its staff for any amendment of the Registration Statement, or for any supplement to the Final Prospectus Supplement or for any additional information, (4) of the issuance by the Commission of any stop order suspending the effectiveness of the Registration Statement or of any notice objecting to its use or the institution or threatening of any proceeding for that purpose and (5) of the receipt by the Company of any notification with respect to the suspension of the qualification of the Notes for sale in any jurisdiction or the institution or threatening of any proceeding for such purpose. The Company will use its reasonable efforts to prevent the issuance of any such stop order or the suspension of any such qualification and, upon such issuance, to obtain as soon as possible the withdrawal of such stop order or relief from such occurrence or objection, including, if necessary, by filing an amendment to the Registration Statement or a new registration statement and using its reasonable efforts to have such amendment or new registration statement declared effective as soon as practicable.

(ii)    The Company will prepare the Final Term Sheet and will file the Final Term Sheet pursuant to Rule 433(d) under the Act within the time required by such Rule.

(iii)    If there occurs an event or development as a result of which the Disclosure Package would include an untrue statement of a material fact or would omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made or the circumstances then prevailing, not misleading, the Company will notify promptly the Representatives so that any use of the Disclosure Package may cease until it is amended or supplemented.

(iv)    If, at any time when a prospectus relating to the Notes is required to be delivered under the Act (including in circumstances where such requirement may be satisfied pursuant to Rule 172) in connection with sales by any Underwriter or dealer, any event occurs as a result of which the Final Prospectus Supplement as then amended or supplemented would include an untrue statement of a material fact or omit to state any material fact necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading, or if it is necessary at any time to amend the Registration Statement, file a new registration statement or supplement the Final Prospectus Supplement to comply with the Act or the Exchange Act or the respective rules thereunder, including in connection with use or delivery of the Final Prospectus Supplement, the Company will promptly notify the Representatives of such event and will promptly prepare and file with the Commission (subject to the first sentence of Section 5(a)(i) above), at its own expense, an amendment or supplement or new registration statement which will correct such statement or omission or an amendment which will effect such compliance. The Company will also use its reasonable efforts to have any amendment to the Registration Statement or new registration statement declared effective as soon as practicable in order to avoid any disruption in use of the Final Prospectus Supplement and supply any amended or supplemented Final Prospectus Supplement to you in such quantities as you may reasonably request. Neither the Representatives’ consent to, nor the Underwriters’ delivery of, any such amendment or supplement shall constitute a waiver of any of the conditions set forth in Section 7 hereof.

(v)    As soon as practicable, the Company will make generally available to its securityholders and to the Representatives an earnings statement (which need not be audited) of the Company and its subsidiaries satisfying the provisions of Section 1l(a) of the Act and Rule 158 under the Act.

(vi)    Upon request, the Company will furnish to the Representatives and counsel for the Underwriters, without charge, copies of the Registration Statement (one of which will be signed and including exhibits thereto) and to each other Underwriter a copy of the Registration Statement (without exhibits thereto), and, so long as a prospectus relating to the Notes is required to be delivered under the Act (including in circumstances where such requirement may be satisfied pursuant to Rule 172) in connection with sales by any Underwriter or dealer, each Preliminary Prospectus Supplement, the Final Prospectus Supplement and each Issuer Free Writing Prospectus and all amendments and supplements to such documents, in each case in such quantities as the Representatives reasonably request.

(vii)    The Company will arrange, if necessary, for the qualification of the Notes for sale under the laws of such jurisdictions as the Representatives reasonably designate and will continue such qualifications in effect so long as required for the distribution of the Notes; provided, however, that, in connection therewith, the Company shall not be required to qualify as a foreign company or corporation or as a dealer in securities in any jurisdiction in which it is not so qualified, or to file a general consent to service of process in any jurisdiction, or to subject itself to material taxation in respect of doing business in any jurisdiction in which it is not otherwise so subject.

(viii)    The Company will not take, directly or indirectly, any action designed to or that would constitute or that might reasonably be expected to cause or result in, under the Exchange Act or otherwise, stabilization or manipulation of the price of any security of the Company to facilitate the sale or resale of the Notes.

(ix)     Until 14 days following the Closing Date, the Company will not, without the prior written consent of the Representatives, directly or indirectly, issue, sell, offer to sell, grant any option for the sale of or otherwise dispose of, any debt securities that are substantially similar to the Notes (including, without limitation, with respect to the maturity, currency, interest rate and other material terms thereof).

(x)    The Company shall apply the net proceeds of its sale of the Notes as set forth in the Registration Statement, Disclosure Package and the Final Prospectus Supplement.

(xi)    The Company will comply with all agreements set forth in the representation letters of the Company to DTC relating to the acceptance of the Notes for “book-entry” transfer through the facilities of DTC.

(xii) The Company will, whether or not this Agreement becomes effective or is terminated or the sale of the Notes to the Underwriters is consummated, pay all reasonable fees, expenses, costs and charges in connection with: (i) the preparation, printing, filing, delivery and shipping of the Registration Statement, the Disclosure Package, the Final Prospectus Supplement and each Issuer Free Writing Prospectus and any amendments or supplements thereto; (ii) the printing, producing, copying and delivering the Indenture and the other closing documents (including any compilations thereof) and any other agreements, memoranda, correspondence and other documents printed and delivered in connection with the offering, purchase, sale and delivery of the Notes; (iii) the services of the Company’s independent registered public accounting firms; (iv) the services of the Company’s counsel; (v) the qualification of the Notes under the securities laws of the several jurisdictions as provided in Section 5(a)(vii) hereof and the preparation, printing and distribution of a Blue Sky Memorandum (including the related fees and expenses of counsel to the Underwriters in an amount not to exceed $15,000); (vi) any rating of the Notes by rating agencies; (vii) any required review by the Financial Industry Regulatory Authority, Inc. of the terms of the sale of the Notes; (viii) the services of the Trustee and any agent of the Trustee (including the fees and disbursements of counsel for the Trustee); (ix) any “roadshow” or other investor presentations relating to the offering of the Notes (including, without limitation, the expenses of Company personnel for meetings and travel); and (x) such reasonable fees, expenses, costs and charges otherwise incident to the performance of its obligations hereunder for which provision is not otherwise made in this Section 5(a)(xii) (excluding any stamp duty (including any interest and penalties) which arise solely as a result of any written instrument of transfer which effects the sale and delivery of the Notes hereunder being executed in, or brought to, the United Kingdom).

(b)     It is understood, however, that, except as provided in Section 5(a)(xii) or Sections 8 and 9 hereof, the Underwriters will pay all of their own costs and expenses, including the fees and expenses of counsel to the Underwriters and any advertising expenses incurred in connection with the offering of the Notes. If the sale of the Notes provided for herein is not consummated by reason of acts of the Company or changes in circumstances of the Company pursuant to Section 9 of this Agreement which prevent this Agreement from becoming effective, or by reason of any failure, refusal or inability on the part of the Company to perform any agreement on its part to be performed or because any other condition of the Underwriters’ obligations hereunder is not fulfilled or if the Underwriters decline to purchase the Notes for any reason permitted under this Agreement, the Company will reimburse the Underwriters for all reasonable out-of-pocket disbursements (including fees and expenses of counsel to the Underwriters) incurred by the Underwriters in connection with any investigation or preparation made by them in respect of the marketing of the Notes or in contemplation of the performance by them of their obligations hereunder.

6. Free Writing Prospectuses. (i) The Company agrees that, unless it has obtained or obtains, as the case may be, the prior written consent of the Representatives, which consent will not be unreasonably withheld or delayed, and (ii) each Underwriter, severally and not jointly, agrees with the Company that, unless it has obtained or obtains, as the case may be, the prior written consent of the Company, it has not made and will not make any offer relating to the Notes that would constitute an Issuer Free Writing Prospectus or that would otherwise constitute a “free writing prospectus” (as defined in Rule 405) required to be filed by the Company with the Commission or retained by the Company under Rule 433 under the Act, other than a free writing prospectus containing the information contained in the Final Term Sheet; provided that the prior written consent of the parties hereto shall be deemed to have been given in respect of the Free Writing Prospectuses, if any, included in Schedule III hereto. Any such free writing prospectus consented to by the Representatives or the Company is hereinafter referred to as a “Permitted Free Writing Prospectus.” The Company agrees that (x) it has treated and will treat, as the case may be, each Permitted Free Writing Prospectus as an Issuer Free Writing Prospectus and (y) it has complied and will comply, as the case may be, with the requirements of Rules 164 and 433 under the Act applicable to any Permitted Free Writing Prospectus, including in respect of timely filing with the Commission, legending and record keeping.

7.    Conditions of the Obligations of the Underwriters. The several obligations of the Underwriters to purchase and pay for the Notes on the Closing Date will be subject to the accuracy of the representations and warranties on the part of the Company herein as of the Applicable Time and as of the Closing Date, to the accuracy of the statements of Company officers made pursuant to the provisions hereof, to the performance by the Company of its obligations hereunder, and to the following additional conditions precedent:

(a)    The Underwriters shall have received, on each of the date hereof and the Closing Date, letters dated the date hereof or the Closing Date, as the case may be, in forms and substance satisfactory to the Representatives, from each of Ernst & Young LLP and Ernst & Young Ltd., the previous and current independent public accountants of the Company, respectively, containing statements and information of the type ordinarily included in accountants’ “comfort letters” to underwriters with respect to the financial statements and certain financial information contained in the Disclosure Package and the Final Prospectus Supplement; provided that the letters from Ernst & Young Ltd. shall use a “cut-off date” not earlier than two business days prior to the Closing Date.

(b)    The Final Prospectus Supplement shall have been filed with the Commission in accordance with Rule 424(b) under the Act and Section 5(a) of this Agreement. Prior to the Closing Date, no stop order suspending the effectiveness of a Registration Statement shall have been issued and no proceedings for that purpose shall have been instituted or threatened by the Commission.

(c)    Subsequent to the execution and delivery of this Agreement and prior to the Closing Date,

(i)     there shall not have occurred any downgrading, nor shall the Company have received any notice from any “nationally recognized statistical rating organization,” as such term is defined in Section 3(a)(62) under the Exchange Act of any intended or potential downgrading or of any review for a possible change that does not indicate the direction of the possible change, in the rating accorded the Company or any of the securities of the Company or any of its subsidiaries or in the rating outlook for the Company; and

(ii)    there shall not have occurred any change, or any development involving a prospective change, in the condition, financial or otherwise, or in the earnings, business or operations of the Company and its subsidiaries, taken as a whole, from that set forth in the Disclosure Package that, in the judgment of the Representatives, is material and adverse and that makes it, in the judgment of the Representatives, impracticable or inadvisable to proceed with the offer, sale and delivery of the Notes on the terms and in the manner contemplated in this Agreement and the Disclosure Package.

(d)    Sidley Austin LLP, United States counsel for the Company, shall have furnished to the Representatives such opinion or opinions, including a negative assurance statement, in form and substance reasonably satisfactory to the Representatives.

(e)    Walkers (Bermuda) Limited, Bermuda counsel for the Company, shall have furnished to the Representatives its opinion dated the Closing Date, in form and substance reasonably satisfactory to the Representatives.

(f)    The Representatives shall have received from Cleary Gottlieb Steen & Hamilton LLP, counsel for the Underwriters, such opinion or opinions, including a negative assurance statement, dated the Closing Date and addressed to the Representatives, with respect to the issuance and sale of the Notes, the Indenture, the Final Prospectus Supplement and Disclosure Package and other related matters as the Representatives may reasonably require, and the Company shall have furnished to such counsel such documents as they request for the purpose of enabling them to pass upon such matters. In rendering such opinion, Cleary Gottlieb Steen & Hamilton LLP may rely, as to matters governed by the laws of Bermuda, upon the opinion of counsel for the Company referred to in Section 7(e).

(g)    The Company shall have furnished to the Representatives a certificate of the Company, signed by two officers, who shall be any of the chief executive officer, the chief financial officer, the chief underwriting officer, the general counsel and the group president of the Company, dated the Closing Date, to the effect that the signers of such certificate have carefully examined the Registration Statement, the Disclosure Package and the Final Prospectus Supplement and this Agreement and that:

(i)    the representations and warranties of the Company in this Agreement are true and correct on and as of the Closing Date, with the same effect as if made on the Closing Date and the Company has complied in all material respects with all the agreements and satisfied all the conditions on its part to be performed or satisfied at or prior to the Closing Date;

(ii) the signers of such certificate have carefully examined the Registration Statement, the Disclosure Package and the Final Prospectus Supplement, and any amendments or supplements thereto (including any documents incorporated or deemed to be incorporated by reference into the Registration Statement, the Disclosure Package and the Final Prospectus Supplement), and, in their opinion, the Registration Statement, as of the Effective Date, the Disclosure Package, as of the Applicable Time, and the Final Prospectus Supplement, as of its date, did not and, on the Closing Date, will not include any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein, in light of the circumstances under which they were made, not misleading;

(iii)    since the date of the Preliminary Prospectus Supplement, there has occurred no event required to be set forth in an amendment or supplement to the Disclosure Package or the Final Prospectus Supplement which has not been so set forth and there has been no document required to be filed under the Act or the Exchange Act that upon such filing would be deemed to be incorporated by reference into the Registration Statement, Disclosure Package or the Final Prospectus Supplement that has not been so filed;

(iv)    since the date of the most recent financial statements included or incorporated by reference in the Preliminary Prospectus Supplement and the Final Prospectus Supplement (exclusive of any amendment or supplement thereto), there has been no Material Adverse Effect, except as set forth in or contemplated in the Registration Statement, the Preliminary Prospectus Supplement and the Final Prospectus Supplement (exclusive of any amendment or supplement thereto); and

(v)    no stop order suspending the effectiveness of the Registration Statement or notice by the Commission objecting to its use has been issued and no proceedings for that purpose have been instituted or, to the Company’s knowledge, threatened.

(h)    The Representatives shall have received, on each of the date hereof and the Closing Date, a certificate or certificates, dated the respective date of delivery thereof, of the Chief Financial Officer of the Company with respect to certain financial data contained or incorporated by reference in the Registration Statement, the Disclosure Package and the Final Prospectus Supplement, providing “management comfort” with respect to such information, in form and substance reasonably satisfactory to the Representatives.

(i)    The Company shall have provided the Representatives with copies of such additional opinions, certificates, letters and documents as the Representatives reasonably request.

(j)    On the Closing Date, the Notes shall be rated at least “Baa2” by Moody’s and “BBB-” by S&P, and the Company shall have delivered to the Representatives a letter, or other evidence satisfactory to the Representatives, confirming that the Notes have such ratings.

(k)    Prior to the Closing Date, the Company shall have furnished to the Representatives such further information, certificates and documents as the Representatives may reasonably request. If any of the conditions specified in this Section 7 shall not have been fulfilled in all material respects when and as provided in this Agreement, or if any of the opinions and certificates mentioned above or elsewhere in this Agreement shall not be in all material respects reasonably satisfactory in form and substance to the Representatives and counsel for the Underwriters, this Agreement and all obligations of the Underwriters hereunder may be canceled at, or at any time prior to, the Closing Date by the Representatives. Notice of such cancellation shall be given to the Company in writing or by telephone or facsimile confirmed in writing.

8.    Indemnification and Contribution.

(a)    The Company hereby agrees to indemnify and hold harmless each Underwriter, its affiliates, directors, officers and employees and each person, if any, who controls any Underwriter within the meaning of Section 15 of the Act or Section 20 of the Exchange Act, from and against any loss, claim, damage or liability, joint or several, or any action in respect thereof (including, but not limited to, any loss, claim, damage, liability or action relating to purchases and sales of Notes), to which that Underwriter, affiliate, director, officer, employee or controlling person may become subject, under the Act or otherwise, insofar as such loss, claim, damage, liability or action arises out of, or is based upon, (i) any untrue statement or alleged untrue statement of a material fact contained in (A) the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any amendment thereof or supplement thereto, (B) Blue Sky application or other document prepared or executed by the Company (or based upon any written information furnished by the Company) specifically for the purpose of qualifying any or all of the Notes under the securities laws of any state or other jurisdiction (any such application, document or information being hereinafter called a “Blue Sky Application”), or (C) materials or information provided to investors by, or with the approval of, the Company in connection with the marketing of the offering of the Notes (“Marketing Materials”), including any road show or investor presentations made to investors by the Company (whether in person or electronically), or (ii) the omission or alleged omission to state in the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any amendment thereof or supplement thereto, or in any Blue Sky Application or in any Marketing Materials, any material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading, and shall reimburse each Underwriter and each such affiliate, director, officer, employee or controlling person promptly upon demand for any legal or other expenses reasonably incurred by that Underwriter, affiliate, director, officer, employee or controlling person in connection with investigating or defending or preparing to defend against any such loss, claim, damage, liability or action as such expenses are incurred; provided, however, that the Company shall not be liable in any such case to the extent that any such loss, claim, damage, liability or action arises out of, or is based upon, any untrue statement or alleged untrue statement or omission or alleged omission made in the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any amendment thereof or supplement thereto, or in any Blue Sky Application or in any Marketing Materials, in reliance upon and in conformity with written information furnished to the Company through the Representatives by or on behalf of any Underwriter specifically for inclusion therein, which information consists solely of the information specified in Section 8(e). The foregoing indemnity agreement is in addition to any liability that the Company may otherwise have to any Underwriter or to any affiliate, director, officer, employee or controlling person of that Underwriter.

(b) Each Underwriter, severally and not jointly, hereby agrees to indemnify and hold harmless the Company, its officers and employees, each of its directors, and each person, if any, who controls the Company within the meaning of Section 15 of the Act or Section 20 of the Exchange Act, from and against any loss, claim, damage or liability, joint or several, or any action in respect thereof, to which the Company or any such director, officer, employee or controlling person may become subject, under the Act or otherwise, insofar as such loss, claim, damage, liability or action arises out of, or is based upon, (i) any untrue statement or alleged untrue statement of a material fact contained in (A) the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any amendment thereof or supplement thereto, (B) Blue Sky Application, or (C) Marketing Materials, or (ii) the omission or alleged omission to state in the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any amendment thereof or supplement thereto, or in any Blue Sky Application or in any Marketing Materials any material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading, but in each case only to the extent that the untrue statement or alleged untrue statement or omission or alleged omission was made in reliance upon and in conformity with written information furnished to the Company through the Representatives by or on behalf of that Underwriter specifically for inclusion therein, which information consists solely of the information specified in Section 8(e). The foregoing indemnity agreement is in addition to any liability that any Underwriter may otherwise have to the Company or any such director, officer, employee or controlling person.

(c) Promptly after receipt by an indemnified party under this Section 8 of notice of any claim or the commencement of any action, the indemnified party shall, if a claim in respect thereof is to be made against the indemnifying party under this Section 8 notify the indemnifying party in writing of the claim or the commencement of that action; provided, however, that the failure to notify the indemnifying party shall not relieve it from any liability that it may have under paragraphs (a) or (b) above except to the extent it has been materially prejudiced (through the forfeiture of substantive rights or defenses) by such failure and; provided, further, that the failure to notify the indemnifying party shall not relieve the indemnifying party from any liability that it may have to an indemnified party otherwise than under paragraphs (a) or (b) above. If any such claim or action shall be brought against an indemnified party, and it shall notify the indemnifying party thereof, the indemnifying party shall be entitled to participate therein and, to the extent that it wishes, jointly with any other similarly notified indemnifying party, to assume the defense thereof with counsel reasonably satisfactory to the indemnified party. After notice from the indemnifying party to the indemnified party of its election to assume the defense of such claim or action, the indemnifying party shall not be liable to the indemnified party under this Section 8 for any legal or other expenses subsequently incurred by the indemnified party in connection with the defense thereof other than reasonable costs of investigation; provided, however, that the indemnified party shall have the right to employ counsel to represent jointly the indemnified party and those other indemnified parties and their respective directors, officers, employees and controlling persons who may be subject to liability arising out of any claim in respect of which indemnity may be sought under this Section 8, if (i) the indemnified party and the indemnifying party shall have so mutually agreed; (ii) the indemnifying party has failed within a reasonable time to retain counsel reasonably satisfactory to the indemnified party; (iii) the indemnified party and its directors, officers, employees and controlling persons shall have reasonably concluded that there may be legal defenses available to them that are different from or in addition to those available to the indemnifying party; or (iv) the named parties in any such proceeding (including any impleaded parties) include both the indemnified parties or their respective directors, officers, employees or controlling persons, on the one hand, and the indemnifying party, on the other hand, and representation of both sets of parties by the same counsel would be inappropriate due to actual or potential differing interests between them, and in any such event the fees and expenses of such separate counsel shall be paid by the indemnifying party. No indemnifying party shall (x) without the prior written consent of the indemnified parties (which consent shall not be unreasonably withheld), settle or compromise or consent to the entry of any judgment with respect to any pending or threatened claim, action, suit or proceeding in respect of which indemnification or contribution may be sought hereunder (whether or not the indemnified parties are actual or potential parties to such claim or action) unless such settlement, compromise or consent includes an unconditional release of each indemnified party from all liability arising out of such claim, action, suit or proceeding and does not include a statement as to, or an admission of fault, culpability or a failure to act by or on behalf of any indemnified party, or (y) be liable for any settlement of any such action effected without its written consent (which consent shall not be unreasonably withheld), but if settled with the consent of the indemnifying party or if there be a final judgment of the plaintiff in any such action, the indemnifying party agrees to indemnify and hold harmless any indemnified party from and against any loss or liability by reason of such settlement or judgment. Notwithstanding the foregoing sentence, if at any time an indemnified party shall have requested an indemnifying party to reimburse the indemnified party for fees and expenses of counsel as contemplated by Section 8(a) or (b) hereof, the indemnifying party agrees that it shall be liable for any settlement of any proceeding effected without its written consent if (i) such settlement is entered into more than 30 days after receipt by such indemnifying party of the aforesaid request and (ii) such indemnifying party shall not have reimbursed the indemnified party in accordance with such request or disputed in good faith the indemnified party’s entitlement to such reimbursement prior to the date of such settlement.

(d) If the indemnification provided for in this Section 8 shall for any reason be unavailable to or insufficient to hold harmless an indemnified party under Section 8(a) or 8(b) in respect of any loss, claim, damage or liability, or any action in respect thereof, referred to therein, then each indemnifying party shall, in lieu of indemnifying such indemnified party, contribute to the amount paid or payable by such indemnified party as a result of such loss, claim, damage or liability, or action in respect thereof, (i) in such proportion as shall be appropriate to reflect the relative benefits received by the Company, on the one hand, and the Underwriters, on the other hand, from the offering of the Notes, or (ii) if the allocation provided by clause (i) above is not permitted by applicable law, in such proportion as is appropriate to reflect not only the relative benefits referred to in clause (i) above but also the relative fault of the Company, on the one hand, and the Underwriters, on the other hand, with respect to the statements or omissions that resulted in such loss, claim, damage or liability, or action in respect thereof, as well as any other relevant equitable considerations. The relative benefits received by the Company, on the one hand, and the Underwriters, on the other hand, with respect to such offering shall be deemed to be in the same proportion as the total net proceeds from the offering of the Notes purchased under this Agreement (before deducting expenses) received by the Company, on the one hand, and the total underwriting discount received by the Underwriters with respect to the Notes purchased under this Agreement, on the other hand, bear to the total gross proceeds from the offering of the Notes under this Agreement as set forth on the cover page of the Final Prospectus Supplement. The relative fault shall be determined by reference to whether the untrue or alleged untrue statement of a material fact or omission or alleged omission to state a material fact relates to information supplied by the Company, or the Underwriters, the intent of the parties and their relative knowledge, access to information and opportunity to correct or prevent such statement or omission. The Company and the Underwriters agree that it would not be just and equitable if contributions pursuant to this Section 8(d) were to be determined by pro rata allocation (even if the Underwriters were treated as one entity for such purpose) or by any other method of allocation that does not take into account the equitable considerations referred to herein. The amount paid or payable by an indemnified party as a result of the loss, claim, damage or liability, or action in respect thereof, referred to above in this Section 8(d) shall be deemed to include, for purposes of this Section 8(d), any legal or other expenses reasonably incurred by such indemnified party in connection with investigating or defending any such action or claim. Notwithstanding the provisions of this Section 8(d), no Underwriter shall be required to contribute any amount in excess of the amount by which the total underwriting discounts and commissions received by such Underwriter with respect to the offering of the Notes exceeds the amount of any damages that such Underwriter has otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged omission. No person guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of the Act) shall be entitled to contribution from any person who was not guilty of such fraudulent misrepresentation. The Underwriters’ obligations to contribute as provided in this Section 8(d) are several in proportion to their respective purchase obligations and not joint.

(e)    The Underwriters severally confirm and the Company acknowledges and agrees that the statements with respect to the offering of the Notes by the Underwriters set forth in the fourth paragraph of the section entitled “Underwriting (Conflicts of Interest)” in the Preliminary Prospectus Supplement and the Final Prospectus Supplement, the first sentence of the eighth paragraph of the section entitled “Underwriting (Conflicts of Interest)” in the Preliminary Prospectus Supplement and the Final Prospectus Supplement and the first sentence of the eleventh paragraph of the section entitled “Underwriting (Conflicts of Interest)” in the Preliminary Prospectus Supplement and the Final Prospectus Supplement are correct and constitute the only information furnished in writing to the Company by or on behalf of the Underwriters specifically for inclusion in the Registration Statement for the registration of the Notes as originally filed or in any amendment thereof, or in the Preliminary Prospectus Supplement, the Final Prospectus Supplement, any Issuer Free Writing Prospectus or the information contained in the Final Term Sheet, or in any Blue Sky Application or Marketing Materials.

9.    Termination. The Underwriters may terminate this Agreement by notice given by the Representatives to the Company, if after the execution and delivery of this Agreement and prior to the Closing Date (i) trading generally shall have been suspended or materially limited on, or by, as the case may be, any of the New York Stock Exchange or the Nasdaq Global Market, (ii) trading of any securities of the Company shall have been suspended on the New York Stock Exchange, (iii) a material disruption in securities settlement, payment or clearance services in the United States shall have occurred, (iv) the domestic market for U.S. Treasury securities or

derivatives shall have closed or there shall have occurred a general suspension, material limitation or significant disruption of trading in the domestic market for U.S. Treasury securities or derivatives, (v) any moratorium on commercial banking activities shall have been declared by Federal or New York State authorities or (vi) there shall have occurred any outbreak or escalation of hostilities, or any change in financial markets or any calamity or crisis that, in the Representatives’ judgment, is material and adverse and which, singly or together with any other event specified in this clause (vi), makes it, in the Representatives’ judgment, impracticable or inadvisable to proceed with the offer, sale or delivery of the Notes on the terms and in the manner contemplated in the Disclosure Package or the Final Prospectus Supplement.

If this Agreement shall be terminated by the Underwriters, or any of them, (i) because of any failure or refusal on the part of the Company to comply with the terms or to fulfil any of the conditions of this Agreement (other than by reason of a default by any of the Underwriters), or (ii) if for any reason the Company shall be unable to perform their respective obligations under this Agreement, the Company will reimburse the Underwriters or such Underwriters as have so terminated this Agreement with respect to themselves, severally, through the Representatives for all out of pocket expenses (including the reasonable fees and disbursements of their counsel) reasonably incurred by such Underwriters in connection with this Agreement or the offering contemplated hereunder.

10.    Default of Underwriters. If any Underwriter or Underwriters default in their obligations to purchase Notes hereunder on the Closing Date, and the aggregate principal amount of Notes that such defaulting Underwriter or Underwriters agreed but failed to purchase does not exceed 10% of the aggregate principal amount of the Notes to be purchased by the Underwriters on the Closing Date, the Representatives may make arrangements satisfactory to the Company for the purchase of such Notes by other persons, including any of the Underwriters, but if no such arrangements are made by such Closing Date, the non-defaulting Underwriters shall be obligated severally, in proportion to their respective commitments hereunder, to purchase the Notes that such defaulting Underwriters agreed but failed to purchase on such Closing Date. If any Underwriter or Underwriters so default and the aggregate principal amount of Notes that such defaulting Underwriter or Underwriters agreed but failed to purchase exceeds 10% of the aggregate principal amount of the Notes to be purchased on the Closing Date and arrangements satisfactory to the Representatives and the Company for the purchase of such Notes by other persons are not made within 36 hours after such default, this Agreement will terminate without liability on the part of any non-defaulting Underwriter or the Company, except as provided in Section 5(a)(xii) and Section 8. As used in this Agreement, the term “Underwriter” includes any person substituted for an Underwriter under this Section. Nothing herein will relieve a defaulting Underwriter from liability for its default.

11. Representations and Indemnities to Survive. The respective agreements, representations, warranties, indemnities and other statements of the Company or its officers and of the Underwriters set forth in or made pursuant to this Agreement will remain in full force and effect, regardless of any investigation made by or on behalf of any Underwriter or the Company or any of the officers, directors, employees, agents, affiliates or controlling persons referred to in Section 8 hereof, and will survive delivery of and payment for the Notes. The provisions of Sections 5(a)(xii), 5(b), 8, 12, 20 and 23 hereof shall survive the termination or cancellation of this Agreement.

12.    Notices. All communications hereunder will be in writing and, if sent to the Underwriters, will be mailed, delivered or telegraphed and confirmed to the Representatives, (i) Citigroup Global Markets Inc., 388 Greenwich Street, New York, New York 10013, Attention: General Counsel, Facsimile No.: (646) 291-1469, (ii) Lloyds Securities Inc., 1095 Avenue of the Americas, 34th Floor, New York, NY 10036, Attention: US Bond Syndicate, Email: NALSIBondSyndicate@lbusa.com and (iii) HSBC Securities (USA) Inc., 66 Hudson Boulevard, New York, New York 10001, Attention: DCM Legal Americas, Email: tmg.americas@us.hsbc.com, Facsimile No.: (646) 366-3229; provided, however, that any notice to an Underwriter or the Company pursuant to Section 8 will be mailed, delivered or telegraphed and confirmed to such Underwriter; and (b) if sent to the Company, will be mailed, delivered or telegraphed to the address of the Company set forth on the cover of the Registration Statement, Attention: Secretary.

13.    Entire Agreement; No Fiduciary Duty. (a) This Agreement, together with any contemporaneous written agreements and any prior written agreements (to the extent not superseded by this Agreement) that relate to the offering of the Notes, represents the entire agreement between the Company and the Underwriters with respect to the preparation of any Preliminary Prospectus Supplement, the Disclosure Package, the Final Prospectus Supplement, the conduct of the offering, and the purchase and sale of the Notes. (b) The Company acknowledges that in connection with the offering of the Notes: (i) the Underwriters have acted at arm’s length, are not agents or financial advisors of, and owe no fiduciary duties to, the Company or any other person, (ii) the Underwriters owe the Company only those duties and obligations set forth in this Agreement and prior written agreements (to the extent not superseded by this Agreement), if any, and (iii) the Underwriters may have interests that differ from those of the Company. The Company waives to the full extent permitted by applicable law any claims it may have against the Underwriters arising from an alleged breach of fiduciary duty in connection with the offering of the Notes. None of the Underwriters are advising the Company or any other person as to any legal, tax, investment, accounting or regulatory matters in any jurisdiction. The Company shall consult with their own advisors concerning such matters and shall be responsible for making their own independent investigation and appraisal of the transactions contemplated hereby, and none of the Underwriters shall have any responsibility or liability to the Company with respect thereto.

14.    Representation. The Representatives will act for the Underwriters in connection with the transactions contemplated hereby, and any action under this Agreement taken by the Representatives will be binding upon all Underwriters.

15. Waiver of Tax Confidentiality. Notwithstanding anything herein to the contrary, purchasers of the Notes (and each employee, representative or other agent of a purchaser) may disclose to any and all persons, without limitation of any kind, the U.S. tax treatment and U.S. tax structure of any transaction contemplated herein and all materials of any kind (including opinions or other tax analyses) that are provided to the purchasers of the Notes relating to such U.S. tax treatment and U.S. tax structure, other than any information for which nondisclosure is reasonably necessary in order to comply with applicable securities laws.

16.    Research Analyst Independence. The Company acknowledges that the Underwriters’ research analysts and research departments are required to be independent from their respective investment banking divisions and are subject to certain regulations and internal policies, and that such Underwriters’ research analysts may hold views and make statements or investment recommendations and/or publish research reports with respect to the Company and/or the offering that differ from the views of their respective investment banking divisions. The Company hereby waives and releases, to the fullest extent permitted by law, any claims that the Company may have against the Underwriters with respect to any conflict of interest that may arise from the fact that the views expressed by their independent research analysts and research departments may be different from or inconsistent with the views or advice communicated to the Company by such Underwriters’ investment banking divisions. The Company acknowledges that each of the Underwriters is a full service securities firm and as such from time to time, subject to applicable securities laws, may effect transactions for its own account or the account of its customers and hold long or short positions in debt or equity securities of the companies that may be the subject of the transactions contemplated by this Agreement.

17.    USA Patriot Act. In accordance with the requirements of the USA Patriot Act (Title III of Pub. L. 107-56 (signed into law October 26, 2001)), the Underwriters are required to obtain and verify any record information that identifies their respective clients, including the Company, which information may include the name and address of their respective clients, as well as other information that will allow the Underwriters to properly identify their respective clients.

18.    Successors. This Agreement will inure to the benefit of and be binding upon the parties hereto and their respective personal representatives (in the case of a natural person) and successors and the officers and directors and controlling persons referred to in Section 8, and no other person will have any right or obligation hereunder. No purchaser of any of the Notes from any Underwriter shall be deemed a successor or assign merely because of such purchase.

19.    Counterparts. This Agreement may be signed in two or more counterparts, each of which shall be an original, with the same effect as if the signatures thereto and hereto were upon the same instrument. Counterparts may be delivered via facsimile, electronic mail (including any electronic signature covered by the Electronic Signatures in Global and National Commerce Act of 2000, Uniform Electronic Transactions Act, the Electronic Signatures and Records Act or other applicable law (e.g., www.docusign.com)) or other transmission method and any counterpart so delivered shall be deemed to have been duly and validly delivered and be legally valid, effective and enforceable for all purposes.

20.    Applicable Law. This Agreement and any claim, controversy or dispute arising under or related to this Agreement shall be governed by and construed in accordance with the internal laws of the State of New York.

21.    Headings. The headings of the sections of this Agreement have been inserted for convenience of reference only and shall not be deemed a part of this Agreement.

22.    Recognition of the U.S. Special Resolution Regimes. In the event that any Underwriter that is a Covered Entity becomes subject to a proceeding under a U.S. Special Resolution Regime, the transfer from such Underwriter of this Agreement, and any interest and obligation in or under this Agreement, will be effective to the same extent as the transfer would be effective under the U.S. Special Resolution Regime if this Agreement, and any such interest and obligation, were governed by the laws of the United States or a state of the United States.In the event that any Underwriter that is a Covered Entity or a BHC Act Affiliate of such Underwriter becomes subject to a proceeding under a U.S. Special Resolution Regime, Default Rights under this Agreement that may be exercised against such Underwriter are permitted to be exercised to no greater extent than such Default Rights could be exercised under the U.S. Special Resolution Regime if this Agreement were governed by the laws of the United States or a state of the United States.

“BHC Act Affiliate” has the meaning assigned to the term “affiliate” in, and shall be interpreted in accordance with, 12 U.S.C. § 1841(k).

“Covered Entity” means any of the following:

a “covered entity” as that term is defined in, and interpreted in accordance with, 12 C.F.R. § 252.82(b);

a “covered bank” as that term is defined in, and interpreted in accordance with, 12 C.F.R. § 47.3(b); or

a “covered FSI” as that term is defined in, and interpreted in accordance with, 12 C.F.R. § 382.2(b).

“Default Right” has the meaning assigned to that term in, and shall be interpreted in accordance with, 12 C.F.R. §§ 252.81, 47.2 or 382.1, as applicable.

“U.S. Special Resolution Regime” means each of (i) the Federal Deposit Insurance Act and the regulations promulgated thereunder and (ii) Title II of the Dodd-Frank Wall Street Reform and Consumer Protection Act and the regulations promulgated thereunder.

23.    Waiver of Jury Trial; Submission to Jurisdiction.

(a)    Each of the parties hereto hereby waives any right to trial by jury in any suit or proceeding arising out of or relating to this Agreement.

(b) The Company irrevocably (i) agrees that any legal suit, action or proceeding against the Company arising out of or based upon this Agreement or the transactions contemplated hereby may be instituted in any state or federal court located in the Borough of Manhattan, The City of New York, New York (each a “New York Court”), (ii) waives, to the fullest extent it may effectively do so, any objection which it may now or hereafter have to the laying of venue of any such proceeding and (iii) submits to the non-exclusive jurisdiction of such New York Court in any such suit, action or proceeding. The Company agrees that a final judgment in any such suit, action or proceeding shall be conclusive and may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by law. The Company has appointed Cogency Global Inc., 122 East 42nd Street, 18th Floor, New York, NY 10168, as its authorized agent (the “Company’s Authorized Agent”) upon whom process may be served in any such action arising out of or based on this Agreement or the transactions contemplated hereby which may be instituted in any New York Court, expressly consents to the jurisdiction of any such court in respect of any such action, and waives any other requirements of or objections to personal jurisdiction with respect thereto. Such appointment shall be irrevocable. The Company represents and warrants that the Company’s Authorized Agent has agreed to act as such agent for service of process and agrees to take any and all action, including the filing of any and all documents and instruments which may be necessary to continue such appointment in full force and effect as aforesaid. Service of process upon the Company’s Authorized Agent and written notice of such service to the Company shall be deemed, in every respect, effective service of process upon the Company.

(c)    In respect of any judgment or order given or made for any amount due hereunder that is expressed and paid in a currency (the “judgment currency”) other than United States dollars, the party against whom such judgment or order has been given or made will indemnify each party in whose favor such judgment or order has been given or made (the “Indemnitee”) against any loss incurred by the Indemnitee as a result of any variation as between (i) the rate of exchange at which the United States dollar amount is converted into the judgment currency for the purpose of such judgment or order and (ii) the rate of exchange at which the Indemnitee is able to purchase United States dollars with the amount of judgment currency actually received by the Indemnitee. The foregoing indemnity shall constitute a separate and independent obligation of each of the Company and the Underwriters and shall continue in full force and effect notwithstanding any such judgment or order as aforesaid. The term “rate of exchange” shall include any premiums and costs of exchange payable in connection with the purchase of or conversion into United States dollars.

If the foregoing is in accordance with the Representatives’ understanding of our agreement, kindly sign and return to the Company one of the counterparts hereof, whereupon it will become a binding agreement among the Company and the Underwriters in accordance with its terms.

The foregoing Underwriting Agreement is hereby

confirmed and accepted as of the date first above

written.

For themselves and as Representatives of the Several

Underwriters named in Schedule I hereto

Schedule of Underwriters

FWP Final Term Sheet

* A securities rating is not a recommendation to buy, sell or hold securities and may be subject to review, revision, suspension, reduction or withdrawal at any time and should be evaluated independently of any other rating.

** It is expected that delivery of the Notes will be made against payment therefor on the Settlement Date thereof, which is three business days following the Trade Date (such settlement cycle being referred to as “T+3”). Under Rule 15c6-l under the Securities Exchange Act of 1934, as amended, trades in the secondary market generally are required to settle in one business day unless the parties to any such trade expressly agree otherwise. Accordingly, purchasers who wish to trade the Notes before the business day prior to the Settlement Date will be required, by virtue of the fact that the Notes initially will settle in T+3, to specify an alternative settlement cycle at the time of any such trade to prevent a failed settlement. Purchasers of the Notes who wish to trade the Notes during such period should consult their own advisors.

The Issuer has filed a registration statement (including the Preliminary Prospectus Supplement and accompanying prospectus) with the Securities and Exchange Commission (the “SEC”) for the offering to which this communication relates. Before you invest, you should read the Preliminary Prospectus Supplement and accompanying prospectus in that registration statement and other documents the Issuer has filed with the SEC for more complete information about the Issuer and this offering. You may get these documents for free by visiting EDGAR on the SEC’s website at www.sec.gov. Alternatively, the Issuer, any underwriter or any dealer participating in the offering will arrange to send you the Preliminary Prospectus Supplement and accompanying prospectus if you request it by calling Citigroup Global Markets Inc. at 1-800-831-9146, Lloyds Securities Inc. at 1-212-930-5039 or HSBC Securities (USA) Inc. at 1-866-811-8049.

ANY DISCLAIMERS OR OTHER NOTICES THAT MAY APPEAR BELOW ARE NOT APPLICABLE TO THIS COMMUNICATION AND SHOULD BE DISREGARDED. SUCH DISCLAIMERS OR OTHER NOTICES WERE AUTOMATICALLY GENERATED AS A RESULT OF THIS COMMUNICATION BEING SENT VIA BLOOMBERG OR ANOTHER EMAIL SYSTEM.

Final Term Sheet filed pursuant to Rule 433 under the Act, dated June 10, 2025

This Fifth Supplemental Indenture, dated as of June 13, 2025 (the “Fifth Supplemental Indenture”), to the Indenture, dated as of August 16, 2004 (the “Original Indenture”) by and between Aspen Insurance Holdings Limited, a limited company duly organized and existing under the laws of Bermuda, having its principal executive office located at 141 Front Street, Hamilton HM 19, Bermuda (the “Company”), as issuer, and Deutsche Bank Trust Company Americas, a New York banking corporation duly organized and existing under the laws of the State of New York, having its corporate trust office located at 1 Columbus Circle, 4th Floor, New York, NY 10019 (the “Trustee”), as trustee, is effective upon the execution hereof by the parties hereto.

WHEREAS, the Company has heretofore executed and delivered to the Trustee the Original Indenture providing for the issuance from time to time of its notes, debentures or other evidences of its unsecured indebtedness (the “Securities”), unlimited as to principal amount;

WHEREAS, the Original Indenture is incorporated herein by reference and the Original Indenture, as supplemented by this Fifth Supplemental Indenture, is herein called the “Indenture”;

WHEREAS, Section 3.1 of the Original Indenture provides that, with respect to any series of Securities to be authenticated and delivered under the Indenture, the terms of such series of Securities shall be established by (i) a resolution of the Board of Directors and set forth in an Officer’s Certificate or (ii) one or more indentures supplemental to the Original Indenture;

WHEREAS, the Company desires to create, under the Indenture, a series of Securities to be known as its 5.750% Senior Notes due 2030 (the “Senior Notes”), the form and substance of such notes and the terms, provisions and conditions thereof to be set forth as provided in the Original Indenture and this Fifth Supplemental Indenture; and

WHEREAS, all conditions necessary to authorize the execution and delivery of this Fifth Supplemental Indenture and to make it a valid and binding obligation of the Company have been done or performed;

NOW, THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt of which is hereby acknowledged, the Company and the Trustee mutually covenant and agree as follows:

Article I.

Section 1.1.    Definitions. The following defined terms used herein shall have the meanings specified below. Capitalized terms used herein without definition shall have the respective meanings assigned such terms in the Original Indenture. All capitalized terms that are defined herein and also defined in the Original Indenture shall have the meaning specified herein.

“Applicable Supervisory Regulations” means such insurance supervisory laws, rules and regulations relating to group supervision or the supervision of single insurance entities, as applicable, which are applicable to the Insurance Group, and which shall initially mean the Group Rules until such time when the BMA no longer has jurisdiction or responsibility to regulate the Company or the Insurance Group.

“BMA” means the Bermuda Monetary Authority, or, should the Bermuda Monetary Authority no longer have jurisdiction or responsibility to regulate the Insurance Group, as the context requires, a regulator which is otherwise subject to Applicable Supervisory Regulations.

“BMA Approval” means the BMA has given, and not withdrawn by the applicable Redemption Date, its prior consent to the redemption of such Senior Notes.

“BMA Redemption Requirements” has the meaning set forth in Section 2.7(a).

“Business Day” means any day other than (i) a Saturday or Sunday, (ii) a day on which banking institutions in The City of New York are authorized or required by law or executive order to remain closed or (iii) a day on which the corporate trust office of the Trustee is closed for business.

“Commercially Reasonable Efforts” means commercially reasonable efforts consistent with the efforts of a comparable third party in the Company’s industry operating under similar circumstances in the carrying out of obligations to complete the offer and sale of Qualifying Securities, subject to the existence of a Market Disruption Event, in an amount necessary to satisfy the Replacement Capital Obligation, to third parties that are not the Company’s subsidiaries in either public offerings or private placements.

“ECR Condition” has the meaning set forth in Section 2.4(d).

“Enhanced Capital Requirement” means the enhanced capital and surplus requirement applicable to the Insurance Group and as defined in the Insurance Act or, should the Insurance Act or the Group Rules no longer apply to the Insurance Group, any and all other solvency capital requirements defined in the Applicable Supervisory Regulations.

“Final Maturity Date” has the meaning set forth in Section 2.4(a).

“First ECR Condition” has the meaning set forth in Section 2.4(d).

“Group Rules” means the Group Solvency Standards, together with the Group Supervision Rules, as those rules and regulations may be amended or replaced from time to time.

“Group Solvency Standards” means the Insurance (Prudential Standards) (Insurance Group Solvency Requirement) Rules 2011 of Bermuda, as those rules and regulations may be amended or replaced from time to time.

“Group Supervision Rules” means the Insurance (Group Supervision) Rules 2011 of Bermuda, as those rules and regulations may be amended or replaced from time to time.

“Insurance Act” means the Insurance Act 1978 of Bermuda, as amended from time to time.

“Insurance Group” means, on a collective basis, the Company and its subsidiaries that are regulated insurance or reinsurance companies (or part of such regulatory group), of which the BMA is the group supervisor, pursuant to the Applicable Supervisory Regulations.

“Interest Payment Date” means, with respect to the Senior Notes only, January 1 and July 1 of each year.

“Market Disruption Event” means the occurrence or existence of any of the following events or sets of circumstances:

(1)    trading in securities generally (or in the Company’s Ordinary Shares, preference shares or other securities specifically) on the New York Stock Exchange, any other U.S. national or international securities exchange or over-the-counter market on which the Company’s Ordinary Shares, preference shares and/or other securities are then listed or traded shall have been suspended or settlement on any such exchange generally shall have been materially disrupted or minimum prices shall have been established on any such exchange or market by the relevant exchange or by any other regulatory body or governmental agency having jurisdiction, and the establishment of such minimum prices materially disrupts or otherwise has a material adverse effect on trading in, or the issuance and sale of, Qualifying Securities;

(2)    the Company would be required to obtain the consent or approval of holders of the Company’s Ordinary Shares or preference shares (to the extent required) or of a regulatory body (including, without limitation, any securities exchange) or governmental authority to issue or sell Qualifying Securities in order to satisfy the Replacement Capital Obligation, and that consent or approval has not yet been obtained notwithstanding the Company’s Commercially Reasonable Efforts to obtain that consent or approval;

(3)    a banking moratorium shall have been declared by the competent authorities of Bermuda, the United Kingdom, the United States and/or any member state of the European Economic Area (“EEA”) and such moratorium materially disrupts or otherwise has a material adverse effect on trading in, or the issuance and sale of, Qualifying Securities for the purposes of satisfying the Replacement Capital Obligation;

(4)    a material disruption shall have occurred in commercial banking or securities settlement or clearance services in Bermuda, the United Kingdom, the United States and/or any member state of the EEA and such disruption materially disrupts or otherwise has a material adverse effect on trading in, or the issuance and sale of, Qualifying Securities for the purposes of satisfying the Replacement Capital Obligation;

(5)    Bermuda, the United Kingdom, the United States and/or any member state of the EEA shall have become engaged in hostilities, there shall have been an escalation in hostilities involving Bermuda, the United Kingdom, the United States and/or any member state of the EEA, there shall have been a declaration of a national emergency or war by Bermuda, the United Kingdom, the United States, and/or any member state of the EEA or there shall have occurred any other national or international calamity or crisis (including any pandemic or epidemic) and such event materially disrupts or otherwise has a material adverse effect on trading in, or the issuance and sale of, Qualifying Securities for the purposes of satisfying the Replacement Capital Obligation;

(6)    there shall have occurred a material adverse change in general domestic or international economic, political or financial conditions, currency exchange rates or exchange controls, and such change materially disrupts or otherwise has a material adverse effect on trading in, or the issuance and sale of, Qualifying Securities for the purposes of satisfying the Replacement Capital Obligation;

(7)    an event occurs and is continuing as a result of which the offering document for the offer and sale of Qualifying Securities would, in the Company’s reasonable judgment, contain an untrue statement of a material fact or omit to state a material fact required to be stated in that offering document or necessary to make the statements in that offering document not misleading and either (i) the disclosure of that event at such time, in the Company’s reasonable judgment, is not otherwise required by law and would have an adverse effect on the Company’s business in any material respect, (ii) the disclosure relates to a previously undisclosed proposed or pending material business transaction, the disclosure of which would impede, delay or otherwise negatively affect the Company’s ability to consummate that transaction or (iii) the event relates to a previously undisclosed material (re)insurance loss and the disclosure of that event at such time, in the Company’s reasonable judgment, is impeded by the current nature of such event and the extent of losses remain under consideration by the Company’s management pending further information from brokers, cedants or insureds; provided that no single suspension period described in this clause (7) shall exceed 90 consecutive days and multiple suspension periods described in this clause (7) shall not exceed an aggregate of 90 days in any 180-day period; or

(8)    the Company reasonably believes that the offering document for the offer and the sale of Qualifying Securities would not be in compliance with a rule or regulation of the U.S. Securities and Exchange Commission or any other securities regulatory authority or exchange to which the Company is subject (for reasons other than those described in the immediately preceding clause (7)) and the Company is unable to comply with such rule or regulation or such compliance is unduly burdensome; provided that no single suspension period described in this clause (8) shall exceed 90 consecutive days and multiple suspension periods described in this clause (8) shall not exceed an aggregate of 90 days in any 180-day period.

“Ordinary Shares” means the Company’s Class A ordinary shares, par value $0.001 per share.

“Qualifying Securities” means any securities (other than the Company’s Ordinary Shares, rights to purchase the Company’s Ordinary Shares and securities convertible into or exchangeable for the Company’s Ordinary Shares, such as preference shares that are convertible into the Company’s Ordinary Shares) having equal or better capital treatment as the capital represented by the Senior Notes under the Group Rules.

“Regular Record Date” means, with respect to the Senior Notes only, the close of business on the Business Day immediately preceding each Interest Payment Date so long as the Senior Notes remain in book-entry only form, or on December 15 and June 15 immediately preceding each Interest Payment Date, respectively, if the Senior Notes do not remain in book-entry only form.

“RCO Satisfying Issuance” has the meaning set forth in Section 2.4(d).

“Replacement Capital Obligation” has the meaning set forth in Section 2.4(d).

“Replacement Capital Obligation Default” has the meaning set forth in Section 2.4(d).

“Scheduled Maturity Date” has the meaning set forth in Section 2.4(a).

“Second ECR Condition” has the meaning set forth in Section 2.4(d).

“Share Capital” or “capital stock” of any Person means any and all share capital, interests, rights to purchase, warrants, options, participations or other equivalents of or interests in (however designated) equity of such Person, including preferred stock, but excluding any debt securities or other securities convertible into such equity.

“Solvency Test Date” means January 1, 2030 (the date that is six months prior to the Scheduled Maturity Date).

“Treasury Rate” means, with respect to any Redemption Date for the Senior Notes, the yield determined by the Company in accordance with the following two paragraphs.

The Treasury Rate shall be determined by the Company after 4:15 p.m., New York City time (or after such time as yields on U.S. government securities are posted daily by the Board of Governors of the Federal Reserve System), on the third Business Day preceding the Redemption Date based upon the yield or yields for the most recent day that appear after such time on such day in the most recent statistical release published by the Board of Governors of the Federal Reserve System designated as “Selected Interest Rates (Daily)—H.15” (or any successor designation or publication) (“H.15”) under the caption “U.S. government securities—Treasury constant maturities—Nominal” (or any successor caption or heading) (“H.15 TCM”). In determining the Treasury Rate, the Company shall select, as applicable: (1) the yield for the Treasury constant maturity on H.15 exactly equal to the period from the Redemption Date to the Par Call Date (the “Remaining Life”); or (2)

if there is no such Treasury constant maturity on H.15 exactly equal to the Remaining Life, the two yields – one yield corresponding to the Treasury constant maturity on H.15 immediately shorter than and one yield corresponding to the Treasury constant maturity on H.15 immediately longer than the Remaining Life – and shall interpolate to the Par Call Date on a straight-line basis (using the actual number of days) using such yields and rounding the result to three decimal places; or (3) if there is no such Treasury constant maturity on H.15 shorter than or longer than the Remaining Life, the yield for the single Treasury constant maturity on H.15 closest to the Remaining Life. For purposes of this paragraph, the applicable Treasury constant maturity or maturities on H.15 shall be deemed to have a maturity date equal to the relevant number of months or years, as applicable, of such Treasury constant maturity from the Redemption Date.

If on the third Business Day preceding the Redemption Date H.15 TCM is no longer published, the Company shall calculate the Treasury Rate based on the rate per annum equal to the semi-annual equivalent yield to maturity at 11:00 a.m., New York City time, on the second Business Day preceding such Redemption Date of the United States Treasury security maturing on, or with a maturity that is closest to, the Par Call Date, as applicable. If there is no United States Treasury security maturing on the Par Call Date but there are two or more United States Treasury securities with a maturity date equally distant from the Par Call Date, one with a maturity date preceding the Par Call Date and one with a maturity date following the Par Call Date, the Company shall select the United States Treasury security with a maturity date preceding the Par Call Date. If there are two or more United States Treasury securities maturing on the Par Call Date or two or more United States Treasury securities meeting the criteria of the preceding sentence, the Company shall select from among these two or more United States Treasury securities the United States Treasury security that is trading closest to par based upon the average of the bid and asked prices for such United States Treasury securities at 11:00 a.m., New York City time. In determining the Treasury Rate in accordance with the terms of this paragraph, the semi-annual yield to maturity of the applicable United States Treasury security shall be based upon the average of the bid and asked prices (expressed as a percentage of principal amount) at 11:00 a.m., New York City time, of such United States Treasury security, and rounded to three decimal places.

“Winding-Up” will occur, with respect to any Person, if: (i) at any time an order is made, or an effective resolution is passed, for the winding-up of such Person (except, in any such case, a solvent winding-up solely for the purpose of a reorganization, merger or amalgamation or the substitution in place of such Person of a successor in business of such person, the terms of which reorganization, merger, amalgamation or substitution (A) have previously been approved in writing by the Holders of a majority in aggregate principal amount of the outstanding Senior Notes and (B) do not provide that the Senior Notes or any amount in respect thereof shall thereby become payable); or (ii) an administrator of such Person is appointed and such administrator gives notice that it intends to declare and distribute a dividend.

Section 1.2.    Construction. All references herein to Articles and Sections, unless otherwise specified, refer to the corresponding Articles and Sections of this Fifth Supplemental Indenture as they amend or supplement the Original Indenture, and not the Original Indenture or any other document.

Article II.

There is hereby established a new series of Securities under the Indenture with the following terms:

Section 2.1.    Title. The title of the series is “5.750% Senior Notes due 2030”.

Section 2.2.    Principal Amount. There are to be issued by the Company, and authenticated and delivered by the Trustee on the date hereof, $300,000,000 principal amount of Senior Notes, and such principal amount of Senior Notes may be increased from time to time pursuant to Section 3.1 of the Original Indenture. All Senior Notes need not be issued on the same date and such series may be reopened at any time, without the consent of any Holder of the Senior Notes, for issuances of additional Senior Notes, unlimited in principal amount, upon delivery by the Company to the Trustee of either a resolution of the Board of Directors and set forth in an Officer’s Certificate or an indenture supplemental to the Original Indenture, setting forth the original issuance date of such additional Senior Notes. The terms of any such additional Senior Notes will be identical (except for the issue date, the issue price, interest accrued prior to the issue date of the additional Senior Notes and the first Interest Payment Date) to the terms of the Senior Notes initially issued, authenticated and delivered on the date hereof, and with the same CUSIP number as the Senior Notes initially issued, so long as such additional Senior Notes are fungible for U.S. federal income tax purposes with the Senior Notes initially issued. Any such additional Senior Notes will, together with the previously issued Senior Notes, constitute a single series of Securities under the Indenture.

Section 2.3.    Payment of Principal and Interest.

(a)    The principal of the Senior Notes shall be due on the Final Maturity Date. The Senior Notes will bear interest from June 13, 2025 or from the most recent Interest Payment Date to which interest has been paid or duly provided for, at a rate of 5.750% per annum, payable semi-annually in arrears on January 1 and July 1 of each year, commencing on January 1, 2026. The Company will pay interest to the Persons in whose names the Senior Notes are registered on the Regular Record Date for such Interest Payment Date. Interest will be computed on the basis of a 360-day year of twelve 30-day months.

(b) If any Interest Payment Date falls on a day that is not a Business Day, the interest payment will be postponed to the next day that is a Business Day, and no interest on such payment will accrue for the period from and after such Interest Payment Date to the date of the payment. If the Final Maturity Date of the Senior Notes falls on a day that is not a Business Day, the payment of interest and principal shall be made on the next succeeding Business Day, and no interest on such payment will accrue for the period from and after the Final Maturity Date to the date of the payment. If the Redemption Date of the Senior Notes falls on a day that is not a Business Day, the payment of interest, premium, if any, and principal shall be made on the next succeeding Business Day, and no interest on such payment will accrue for the period from and after the Redemption Date to the date of the payment. Interest payments for the Senior Notes will include accrued interest from and including the date of issue or from and including the last date in respect of which interest has been paid, as the case may be, to, but excluding, the applicable Interest Payment Date, Final Maturity Date or Redemption Date, as the case may be. Interest on the Senior Notes which have a Redemption Date after a Regular Record Date, and on or before the following Interest Payment Date, will also be payable to the Persons in whose names the Senior Notes are registered on such Regular Record Date.

(c)    Payment of the principal and interest due at maturity of the Senior Notes shall be made upon surrender of the Senior Notes at the Corporate Trust Office of the Trustee. The principal of, premium, if any, and interest on the Senior Notes shall be paid in Dollars. Payments of principal of, premium, if any, or interest on the Senior Notes will be made, subject to such surrender where applicable, at the option of the Company, by wire transfer to an account maintained by the Paying Agent (as defined below), which will make payments to The Depository Trust Company (“DTC”). Thereafter, such payments will be credited to the DTC participants’ accounts that hold book-entry interests in the Senior Notes represented by one or more global notes registered in the name of DTC or its nominee (the “Global Notes”) and credited by such participants to the accounts of beneficial owners of the Senior Notes. None of the Trustee, the Securities Registrar or the Paying Agent shall have any responsibility or obligation to a DTC participant, any beneficial owner of an interest in a Global Note, or other Person, with respect to the accuracy of the records of DTC or any nominee or participant or member thereof, with respect to any ownership interest in the Senior Notes or with respect to the delivery to any participant, member, beneficial owner or other Person (other than DTC) of any notice or payment of any amount. The Company shall make all payments of principal, premium, if any, interest and any Additional Amounts with respect to Senior Notes held in certificated form to the Holder thereof by wire transfer of immediately available funds to the accounts specified by the Holders thereof or, if no such account is specified, by mailing a check to each such Holder’s registered address.

Section 2.4.    Repayment at Final Maturity.

(a)    Unless the Senior Notes are redeemed prior to maturity, the Senior Notes will mature, and the principal amount of the Senior Notes will become payable on the Final Maturity Date, at a price equal to the principal amount thereof, together with accrued and unpaid interest on the Senior Notes to, but excluding, the Final Maturity Date. The “Final Maturity Date” means (i) July 1, 2030 (the “Scheduled Maturity Date”), if, on the Scheduled Maturity Date, the BMA Redemption Requirements have been satisfied, or (ii) if the BMA Redemption Requirements have not been satisfied as of the Scheduled Maturity Date, the earlier of (A) the date falling ten Business Days after the BMA Redemption Requirements have been satisfied and would continue to be satisfied after giving effect to such payment and (B) the date on which a Winding-Up of the Company occurs.

(b)    If the BMA Redemption Requirements will not be satisfied as of the Scheduled Maturity Date, the Company shall, promptly after the principal executive officer or the principal financial officer of the Company becomes aware or reasonably determines that the BMA Redemption Requirements will not be satisfied, notify the Trustee in writing of such inability (and direct the Trustee to transmit such notice to the Holders of the Senior Notes); provided, however, that the Company shall provide any such notice no later than five Business Days immediately preceding the Scheduled Maturity Date.

(c)    Interest shall continue to accrue and be payable for so long as any of the Senior Notes remain outstanding. In the event the Scheduled Maturity Date and the Final Maturity Date are not the same, failure to repay the Senior Notes on the Scheduled Maturity Date will constitute neither an Event of Default under the Indenture nor a default of any kind and will not give Holders of the Senior Notes or the Trustee any right to accelerate repayment of the Senior Notes or any other remedies. Repayment of the Senior Notes on the Scheduled Maturity Date is obligatory if the BMA Redemption Requirements are satisfied; further, the Replacement Capital Obligation will not apply if the Company remains in compliance with the BMA Redemption Requirements during the period beginning six months prior to the Scheduled Maturity Date.

(d)    If, with respect to the Senior Notes:

(i)    as of the Solvency Test Date or any date thereafter and including on the Scheduled Maturity Date or the Final Maturity Date, as may be applicable, the Company (A) does not have sufficient capital to satisfy the Enhanced Capital Requirement (the “First ECR Condition”) or (B) would not have sufficient capital to satisfy the Enhanced Capital Requirement after giving effect to the repayment of the Senior Notes (the “Second ECR Condition” and, together with the First ECR Condition, each an “ECR Condition”), the Company will be required to promptly begin using Commercially Reasonable Efforts, subject to the existence of a Market Disruption Event, to raise cash proceeds from the issuance of Qualifying Securities in an amount at least equal to the principal amount of the Senior Notes due to be repaid (the “Replacement Capital Obligation”);

(ii)    on or after the Solvency Test Date and prior to the Scheduled Maturity Date, the Company is unable to satisfy any ECR Condition, the Company shall, within ten Business Days of the principal executive officer or the principal financial officer of the Company becoming aware of the Company’s inability to so satisfy such ECR Condition, notify the Trustee in writing of such inability (and direct the Trustee to transmit such notice to the Holders of the Senior Notes); provided, however, that the Company shall provide any such notice no later than the Business Day immediately preceding the Scheduled Maturity Date; and

(iii)    the Scheduled Maturity Date and Final Maturity Date are not the same, after a Final Maturity Date has been established, then (A) the Company shall promptly notify the Trustee in writing of such Final Maturity Date (and direct the Trustee to transmit such notice to the Holders of the Senior Notes); and (B) if the Company will then be unable to satisfy any ECR Condition as of such Final Maturity Date, the Company shall, promptly after the principal executive officer or the principal financial officer of the Company becomes aware of the Company’s inability to so satisfy such ECR Condition, notify the Trustee in writing of such inability (and direct the Trustee to transmit such notice to the Holders of the Senior Notes); provided, however, that the Company shall provide any such notice no later than the Business Day immediately preceding such Final Maturity Date.

If a successful issuance of Qualifying Securities satisfying the Replacement Capital Obligation occurs after the Solvency Test Date, but prior to the Scheduled Maturity Date or the Final Maturity Date, as may be applicable (an “RCO Satisfying Issuance”), then (i) such RCO Satisfying Issuance will constitute an issuance of replacement capital in satisfaction of the BMA Redemption Requirements for redemptions or repayments occurring prior to or on the Scheduled Maturity Date or the Final Maturity Date, as may be applicable, and (ii) the Company shall promptly notify the Trustee of such RCO Satisfying Issuance in writing (and direct the Trustee to transmit such notice to the Holders of the Senior Notes).

Subject to the prior sentence, the Replacement Capital Obligation will continue to apply until the earliest of (i) an RCO Satisfying Issuance, (ii) the BMA Redemption Requirements being satisfied by means other than an RCO Satisfying Issuance; provided that, if the BMA Redemption Requirements cease to be satisfied prior to the Final Maturity Date, the Replacement Capital Obligation will be reinstated or (iii) the occurrence of an Event of Default. Accordingly, the Replacement Capital Obligation will cease to apply if the Company is able to restore the Company’s compliance with the Enhanced Capital Requirement, after giving effect to repayment of the Senior Notes, by a means other than the issuance of Qualifying Securities or with an issuance of Qualifying Securities that is less than the principal amount of the Senior Notes, subject to the reinstatement of the Replacement Capital Obligation as described in the preceding sentence.

Although the Company’s failure to use Commercially Reasonable Efforts to raise sufficient proceeds from the issuance of Qualifying Securities to satisfy the Replacement Capital Obligation, subject to the existence of a Market Disruption Event, would constitute a breach of a covenant under the Indenture (a “Replacement Capital Obligation Default”), it will not in any case constitute a default or an Event of Default under the Indenture or give rise to a right of acceleration of payment of the Senior Notes or any other remedy under the terms of the Indenture or the Senior Notes. The sole remedy for a breach of such covenant is for the Trustee, at the direction of the Holders of at least 25% of the aggregate outstanding principal amount of the Senior Notes, to bring suit for specific performance of the Company’s obligations with respect to the covenant to use Commercially Reasonable Efforts with respect to the Replacement Capital Obligation. No Holder of the Senior Notes may pursue any such remedy under the Indenture unless the Trustee will have failed to act after (i) receiving notice of a breach of such covenant and request by Holders of at least 25% of the aggregate outstanding principal amount of the Senior Notes to bring suit and (ii) receiving an indemnity reasonably satisfactory to it.

For the avoidance of doubt, the Replacement Capital Obligation will not apply at any time while the Enhanced Capital Requirement is satisfied, and if the Company would continue to satisfy the Enhanced Capital Requirement after giving effect to a redemption or repayment of the Senior Notes on the Scheduled Maturity Date or the Final Maturity Date, as may be applicable.

If the Company is subject to a Replacement Capital Obligation, the Company may provide written certification to the Trustee (and direct the Trustee to transmit such notice to the Holders of the Senior Notes) within ten Business Days of the later of (i) the occurrence of a Market Disruption Event or (ii) the beginning of the period of the Replacement Capital Obligation (if such Market Disruption Event occurred prior to the Replacement Capital Obligation period beginning and is continuing) certifying that a Market Disruption Event has occurred and is continuing. If such notice is provided, the Company will be excused from the Company’s obligation to use Commercially Reasonable Efforts to issue Qualifying Securities pursuant to the Replacement Capital Obligation for an initial suspension period of 90 consecutive days following such certification.

The Company may extend a suspension period by providing written certification to the Trustee (and directing the Trustee to transmit such notice to the Holders of the Senior Notes) on or prior to the expiration of such suspension period, certifying that the applicable Market Disruption Event is continuing, in which case, the Company’s obligation to use Commercially Reasonable Efforts to issue Qualifying Securities pursuant to the Replacement Capital Obligation will be excused for an additional 60 consecutive days following such further certification. Following the expiration of the applicable suspension period, the Company’s obligation to use Commercially Reasonable Efforts to issue Qualifying Securities pursuant to the Replacement Capital Obligation shall be reinstated. The Company’s ability to initiate or extend a suspension period in connection with a Market Disruption Event will also be subject to the limits on suspension periods provided for in the definition of Market Disruption Event (if applicable). Notwithstanding the foregoing time limitations as to suspension in connection with a particular Market Disruption Event, the suspension of the Company’s obligations pursuant to the foregoing shall not prohibit the further suspension of obligations in connection with, and the Company shall be entitled to provide separate notices with respect to, any separate and distinct Market Disruption Event(s). In addition, for the avoidance of doubt, the Company shall not be prohibited during any suspension of the requirements to use Commercially Reasonable Efforts during a Market Disruption Event from issuing any Qualifying Securities.

For the avoidance of doubt, the Trustee shall have no responsibility to make any determinations or calculations under the Indenture; nor shall the Trustee be charged with determining, monitoring or knowledge of (i) the Replacement Capital Obligation or any terms thereof, which collectively shall be the Company’s responsibility, (ii) the occurrence or continuation of any Replacement Capital Obligation Default, which shall be made by the Holders of the Senior Notes, (iii) whether Commercially Reasonable Efforts have been made, (iv) whether the conditions to redemption and repayment have been satisfied, (v) whether the BMA Redemption Requirements have been satisfied, (vi) whether a Market Disruption Event has occurred, (vii) whether the Final Maturity Date has occurred or (viii) whether an ECR Condition has been met.

Section 2.5.    Optional Redemption.

(a)    Subject to Section 2.6 and Section 2.7 hereof and, for the avoidance of doubt, the BMA Redemption Requirements, prior to June 1, 2030 (the “Par Call Date”), the Company may redeem the Senior Notes at its option, in whole at any time, or in part from time to time, at a Redemption Price (expressed as a percentage of principal amount and rounded to three decimal places) equal to the greater of: (i)(A) the sum of the present values of the remaining scheduled payments of principal and interest thereon discounted to the Redemption Date (assuming the Senior Notes matured on the Par Call Date) on a semi-annual basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate plus 30 basis points less (B) interest accrued to the date of redemption; and (ii) 100% of the principal amount of the Senior Notes to be redeemed, plus, in either case, any accrued and unpaid interest thereon to, but excluding, the Redemption Date.

(b)    Subject to Section 2.6 and Section 2.7 hereof and, for the avoidance of doubt, the BMA Redemption Requirements, on or after the Par Call Date, the Company may redeem the Senior Notes, in whole at any time, or in part from time to time, at a Redemption Price equal to 100% of the principal amount of the Senior Notes being redeemed plus any accrued and unpaid interest thereon to, but excluding, the Redemption Date.

(c)    The Company’s actions and determinations in determining the Redemption Price shall be conclusive and binding for all purposes, absent manifest error. For the avoidance of doubt, the Trustee shall have no responsibility to determine (or to verify or review the Company’s determination of) the Redemption Price or the Treasury Rate.

(d)    Notwithstanding Section 14.2 of the Original Indenture, for any redemption of the Senior Notes pursuant to Section 2.5 hereof, the Company will send the Holders of the Senior Notes to be redeemed a notice of redemption by first-class mail or electronically at least 10 and not more than 60 days prior to the date fixed for redemption. Notices of redemption may, in the Company’s sole discretion, be subject to one or more conditions precedent, including but not limited to, the consummation of a financing transaction, equity offering, asset disposition or other corporate transaction (or series of transactions) or the satisfaction of the BMA Redemption Requirements. In addition, if such redemption is subject to the satisfaction of any such condition, the notice of redemption may state that, in the Company’s discretion, the Redemption Date may be delayed until such time as such condition shall be satisfied, or such redemption may not occur and such notice may be rescinded in the event that such condition shall not have been satisfied by the Redemption Date, or the Redemption Date so delayed. If the Company elects to redeem fewer than all the Senior Notes outstanding, unless otherwise agreed in a Holder’s redemption agreement, the Trustee, in its sole discretion, will select in a fair and appropriate manner, including pro rata or by lot, the Senior Notes to be redeemed in whole or in part, or, in the case of Global Notes, based on the method required by the Depository, unless otherwise required by law or applicable stock exchange or Depository requirement.

(e)    Unless the Company defaults in the payment of the Redemption Price, the Senior Notes called for redemption shall cease to accrue any interest on and after the Redemption Date.

Section 2.6.    Amendments to Redemption for Tax Purposes. Only with respect to the Senior Notes issued hereunder, Section 4.5 of the Original Indenture is hereby amended with respect to the Senior Notes by deleting the text thereof in its entirety and inserting in its place the following:

“Section 4.5. Redemption for Tax Purposes.

Subject to Section 2.7 of the Fifth Supplemental Indenture and, for the avoidance of doubt, the BMA Redemption Requirements, the Company may redeem the Senior Notes at its option, in whole but not in part, at a Redemption Price equal to 100% of the principal amount of the Senior Notes being redeemed plus any accrued and unpaid interest and Additional Amounts, if any, to, but excluding, the date fixed for redemption, if at any time the Company determines in good faith that as a result of (i) any change in or amendment to the laws or treaties (or any regulations or rulings promulgated under these laws or treaties) of any Taxing Jurisdiction (or of any political subdivision or taxation authority thereof affecting taxation) or any change in the position regarding the application or official interpretation of such laws, treaties, regulations or rulings (including a holding, judgment or order by a court of competent jurisdiction) which change in position becomes effective on or after the issuance of the Senior Notes, or (ii) any action taken by any Taxing Jurisdiction (or any political subdivision or taxing authority thereof affecting taxation) which action is generally applied or is taken with respect to the Company, the Company would be required as of the next Interest Payment Date to pay Additional Amounts with respect to the Senior Notes as provided in Section 4.4 of the Original Indenture as amended by Section 2.8 of this Fifth Supplemental Indenture and such requirements cannot be avoided by the use of reasonable measures (consistent with practices and interpretations generally followed or in effect at the time such measures could be taken) then available. If the Company elects to redeem the Senior Notes under this provision it will give written notice of such election to the Trustee and the Holder of the Senior Notes. If the Company elects to redeem the Senior Notes under this provision it will also mail a notice of redemption at least 30 days but no more than 60 days before the Redemption Date to each Holder of the Senior Notes to be redeemed. Unless the Company defaults in the payment of the Redemption Price, on and after the Redemption Date, interest will cease to accrue on and after the Senior Notes or portions thereof called for redemption. Any such redemption will be subject to Article 14 of the Original Indenture.

Notwithstanding the foregoing, no such notice of redemption will be given earlier than 90 days prior to the earliest date on which the Company would be obliged to make such payment of Additional Amounts or withholding if a payment in respect of the Senior Notes were then due. In any event, prior to the publication or mailing or any notice of redemption of the Senior Notes pursuant to the foregoing, the Company will deliver to the Trustee an opinion of independent tax counsel of recognized standing reasonably satisfactory to the Trustee to the effect that the circumstances referred to above exist. The Trustee will accept such opinion as sufficient evidence of the satisfaction of the conditions precedent described above, in which event it will be conclusive and binding on the Holders of the Senior Notes.”

Section 2.7.    Conditions to Redemption and Repayment.

(a) Notwithstanding anything to the contrary set forth in the Original Indenture, this Fifth Supplemental Indenture or the Senior Notes, (i) prior to June 13, 2028, the Senior Notes may be repaid or redeemed only with BMA Approval, including in instances where the Company or a subsidiary of the Company replaces the capital represented by the Senior Notes to be redeemed or repaid with capital having equal or better capital treatment as the Senior Notes under the Group Rules, (ii) the Senior Notes may be repaid or redeemed after three years from the initial issue date of the Senior Notes without BMA Approval if the Company or a subsidiary of the Company replaces the capital represented by the Senior Notes to be redeemed or repaid with capital having equal or better capital treatment as the Senior Notes under the Group Rules, and (iii) the Senior Notes may not be repaid or redeemed at any time, including on the Scheduled Maturity Date, if the Enhanced Capital Requirement would be breached immediately before or after giving effect to the redemption or repayment of such Senior Notes, unless the Company or a subsidiary of the Company replaces the capital represented by the Senior Notes to be redeemed or repaid with capital having equal or better capital treatment as Senior Notes under the Group Rules (collectively, the “BMA Redemption Requirements”).

(b)    In the event that the Senior Notes are not redeemed or repaid as a result of a failure to satisfy the BMA Redemption Requirements, interest on the Senior Notes will continue to accrue and be paid on each Interest Payment Date until the first date on which final payment on the Senior Notes may be made, at which time the Senior Notes will become due and payable, and will be finally repaid at the principal amount of the Senior Notes, together with any accrued and unpaid interest through, but not including, the date on which final payment on the Senior Notes is made.

(c)    Notwithstanding any provision of the Senior Notes or the Indenture, in the event of non-payment on a scheduled Redemption Date or the Scheduled Maturity Date resulting from a failure to satisfy the BMA Redemption Requirements, the Senior Notes to be redeemed or repaid will not become due and payable on such date, and such non-payment will constitute neither an Event of Default under the Indenture or the Senior Notes nor a default of any kind with respect to the Senior Notes, and will not give Holders of the Senior Notes or the Trustee any right to accelerate repayment of the Senior Notes or any other remedies.

Section 2.8.    Additional Amounts. Section 4.4 of the Original Indenture shall be applicable to the Senior Notes as amended by this Section 2.8:

(a)    clause (c) of Section 4.4 of the Original Indenture is hereby amended with respect to the Senior Notes by deleting the text thereof in its entirety and inserting in its place the following:

“(c)    any tax, assessment or other governmental charge that is imposed or withheld by reason of the failure by the Holder of such Security to comply with any reasonable request by the Company addressed to the Holder within 90 days of such request (A) to provide information concerning the nationality, residence or identity of the Holder or (B) to make any declaration or other similar claim or satisfy any information or reporting requirement, which is required or imposed by statute, treaty, regulation or administrative practice of the relevant Taxing Jurisdiction or any political subdivision thereof as a precondition to exemption from all or part of such tax, assessment or other governmental charge;”

(b)    clause (d) of Section 4.4 of the Original Indenture is hereby amended with respect to the Senior Notes by deleting the text thereof in its entirety and inserting in its place the following:

“(d)     any withholding or deduction required to be made pursuant to any EU Directive on the taxation of savings implementing the conclusions of the ECOFIN Council meetings of 26-27 November 2000, 3 June 2003 or any law implementing or complying with, or introduced in order to conform to, such EU Directive; or”

Section 2.9.    Limitation on Liens on Stock of Designated Subsidiaries. Section 4.6 of the Original Indenture shall be applicable to the Senior Notes as amended by this Section 2.9 by inserting the following at the end of Section 4.6 of the Original Indenture:

“This restriction will not apply to Indebtedness secured by (i) Liens on any shares of Share Capital or Indebtedness of, or acquired from, a Person that is merged or consolidated with or into, or is otherwise acquired by the Company or any Designated Subsidiary; (ii) Liens to secure Indebtedness of a Designated Subsidiary to the Company or another Designated Subsidiary, but only as long as the Indebtedness is owned or held by the Company or such Designated Subsidiary; (iii) Liens existing at the time a subsidiary becomes a Designated Subsidiary; and (iv) any extension, renewal or replacement (or successive extensions, renewals or replacements), in whole or in part, of any Lien referred to in clauses (i) through (iii) above.”

Section 2.10.    Amendments to Event of Default. Only with respect to the Senior Notes issued hereunder, Section 6.1 of the Original Indenture is hereby amended with respect to the Senior Notes by deleting the text thereof in its entirety and inserting in its place the following:

“Section 6.1. Event of Default Defined; Acceleration of Maturity; Waiver of Default.

“Event of Default”, with respect to the Senior Notes, wherever used in the Indenture, means each one of the following events which shall have occurred and be continuing (whatever the reason for such Event of Default and whether it shall be voluntary or involuntary or be effected by operation of law or pursuant to any judgment, decree or order of any court or any order, rule or regulation of any administrative or governmental body):

(a)    default in the payment of any interest on the Senior Notes, or any Additional Amounts payable with respect thereto, when such interest becomes or such Additional Amounts become due and payable, other than if the Company is required to defer a payment due to failure to satisfy the BMA Redemption Requirements, and continuance of such default for a period of 30 days;

(b)    default in the payment of the principal of or any premium, if any, on the Senior Notes, or any Additional Amounts payable with respect thereto, when such principal or premium becomes or such Additional Amounts become due and payable either at the Final Maturity Date, upon any redemption, by declaration of acceleration or otherwise, other than if the Company is required to defer a payment due to failure to satisfy the BMA Redemption Requirements;

(c)    default in the performance, or breach, of any covenant or warranty of the Company contained in the Indenture, and the continuance of such default or breach for a period of 60 days after there has been given by registered or certified mail, to the Company by the Trustee, or to the Company and the Trustee by the Holders of at least 25% in principal amount of the Outstanding Senior Notes, a written notice specifying such default and requiring it to be remedied and stating that such notice is a "Notice of Default" under the Indenture; provided, however, that notwithstanding the foregoing, the Company’s failure to use Commercially Reasonable Efforts or to otherwise satisfy the Replacement Capital Obligation shall in no case be a default or an Event of Default and shall not allow any acceleration or any other similar remedy with respect to the Senior Notes; provided,

further, that the only remedy for a breach of such covenant shall be an action for specific performance with respect to such covenant to use Commercially Reasonable Efforts with respect to the Replacement Capital Obligation;

(d)     default in the payment at maturity of the Company’s Indebtedness in excess of $100,000,000 under any other mortgage, indenture or instrument or if any event of default as defined in any other mortgage, indenture or instrument under which there may be issued, or by which there may be secured or evidenced, any of the Company’s Indebtedness (other than indebtedness which is non-recourse to the Company) happens and results in acceleration of more than $100,000,000 in principal amount of such Indebtedness (after giving effect to any applicable grace period), and such default is not cured or waived or such acceleration is not rescinded or annulled within a period of 60 days after there shall have been given, by registered or certified mail, to the Company by the Trustee or to the Company and the Trustee by the Holders of at least 25% in principal amount of the Outstanding Senior Notes, a written notice specifying such default or event of default and requiring the Company to cause such default to be cured or waived or to cause such acceleration to be rescinded or annulled or to cause such Indebtedness to be discharged and stating that such notice is a “Notice of Default” hereunder;

(e)     the Company shall fail within 60 days to pay, bond or otherwise discharge any uninsured judgment or court order for the payment of money in excess of $100,000,000, which is not stayed on appeal or is not otherwise being appropriately contested in good faith;

(f)     a court having jurisdiction in the premises shall enter a decree or order for relief in respect of the Company in an involuntary case under any applicable bankruptcy, insolvency or other similar law now or hereafter in effect, or, under any such law, (i) appointing a receiver, liquidator, assignee, custodian, trustee or sequestrator (or similar official) of the Company or for any substantial part of its property or (ii) ordering the winding up or liquidation of its affairs, and such decree or order shall remain unstayed and in effect for a period of 60 consecutive days;

(g) the Company shall commence a voluntary case under any applicable bankruptcy, insolvency or other similar law now or hereafter in effect, or, under any such law, (i) consent to the entry of an order for relief in an involuntary case under any such law, (ii) consent to the appointment or taking possession by a receiver, liquidator, assignee, custodian, trustee or sequestrator (or similar official) of the Company or for any substantial part of its property, or (iii) make any general assignment for the benefit of creditors; or

(h) default in the performance or breach of the conditions of Section 11.1 and Section 11.2 of the Original Indenture, and the continuation of such violation for 60 days after there has been given, by registered or certified mail, to the Company by the Trustee or to the Company and the Trustee by the Holders of at least 25% in principal amount of the Outstanding Senior Notes, a written notice specifying such failure to comply and requiring it to be remedied and stating that such notice is a “Notice of Default”.

If an Event of Default described in clause (a), (b), (c), (d), (e) or (h) above (and other than an Event of Default described in clause (f) or (g) of this Section 6.1 and subject to the limitations with respect to the Replacement Capital Obligation described in clause (c) above) occurs and is continuing with respect to the Senior Notes at the time Outstanding, either the Trustee or the Holders of at least 25% in aggregate principal amount of the Senior Notes then Outstanding, by notice in writing to the Company (and to the Trustee if given by Securityholders), may declare the entire principal of all Senior Notes and the interest accrued thereon, if any, to be due and payable immediately, and upon any such declaration the same shall become immediately due and payable.

If any Event of Default described in clause (f) or (g) above occurs and is continuing, all unpaid principal of the Senior Notes then Outstanding and the interest accrued thereon, if any, shall ipso facto become and be immediately due and payable without declaration, presentment, demand or notice of any kind by the Trustee or any Holder of the Senior Notes.

The foregoing provisions, however, are subject to the condition that if, at any time after a declaration of acceleration with respect to the Senior Notes has been made, but before any judgment or decree for the payment of the moneys due shall have been obtained or entered as hereinafter provided, the Company shall pay or shall deposit with the Trustee a sum sufficient to pay all matured installments of interest, if any, and any Additional Amounts with respect to all the Senior Notes and the principal of (and premium, if any, on) any and all Senior Notes which shall have become due otherwise than by acceleration and all amounts payable to the Trustee pursuant to the provisions of Section 7.6, and such amount as shall be sufficient to cover reasonable compensation to the Trustee, its agents, attorneys and counsel, and all other expenses and liabilities incurred, and all advances made, by the Trustee except as a result of its negligence or bad faith, and if any and all Events of Default under the Indenture, other than the nonpayment of the principal of and accrued interest on and any Additional Amounts with respect to Senior Notes which shall have become due by acceleration, shall have been cured, waived or otherwise remedied as provided herein - then and in every such case the Holders of a majority in aggregate principal amount of the Senior Notes then Outstanding, by written notice to the Company and to the Trustee, may waive all defaults with respect to the Senior Notes and rescind and annul such acceleration and its consequences, but no such waiver or rescission and annulment shall extend to or shall affect any subsequent default or shall impair any right consequent thereon.

All references to “or Section 6.1(i)” in the Original Indenture shall be deleted and of no effect.”

Section 2.11.    Form, Currency and Denominations. The Senior Notes shall be issued in fully registered form, without coupons, in minimum denominations of $2,000 and integral multiples of $1,000 in excess thereof. The Senior Notes will be issued in substantially the form set forth in Exhibit A hereto. The Depository with respect to the Senior Notes shall be The Depository Trust Company, New York, New York.

Section 2.12.    Global Securities.

(a)    The Senior Notes will be issued in the form of one or more Global Securities registered in the name of the Depository or its nominee. Except under the circumstances set forth in Section 3.6 of the Original Indenture, the Global Securities will not be exchangeable for, and will not otherwise be issuable as, Senior Notes in definitive form. Owners of beneficial interests in such a Global Security will not be considered the registered owners or Holders of the Senior Notes for any purpose.

(b)    No Security representing a Senior Note shall be exchangeable, except for another Global Security of like denomination and tenor to be registered in the name of the Depository or its nominee or to a successor Depository or its nominee. Payment of principal of, any premium or interest on, and any Additional Amounts, if applicable, in respect of, any Senior Note in global form shall be made to the registered Holder thereof.

Section 2.13.    Ranking. The Senior Notes will represent the Company’s direct, unsecured obligations and will rank equal in right of payment to the Company’s existing and future unsecured indebtedness that is not so subordinated. The Senior Notes will be effectively subordinated to the Company’s existing and future secured indebtedness to the extent of the value of the assets securing such indebtedness. The Senior Notes will be structurally and contractually subordinated in right of payment to all obligations of the Company’s subsidiaries, including all existing and future policyholder obligations of the Company’s subsidiaries.

Section 2.14.    Miscellaneous. The Company is not obligated to redeem or purchase any Senior Notes pursuant to any sinking fund or analogous provision. The Senior Notes will not be convertible into Ordinary Shares of the Company and/or exchangeable for other securities. The amount of payments of principal with respect to the Senior Notes shall not be determined with reference to an index, formula or other method or methods. No Senior Notes are issuable upon the exercise of warrants. Each of Section 12.2(b) of the Original Indenture relating to defeasance and Section 12.2(c) of the Original Indenture relating to covenant defeasance shall be applicable to the Senior Notes.

Section 2.15.    Amendments to Section 10.1 and Section 10.2 of the Original Indenture. Only with respect to the Senior Notes issued hereunder, Section 10.1 and Section 10.2 of the Original Indenture are hereby amended as follows:

(a)    Section 10.1(j) of the Original Indenture shall be deleted in its entirety;

(b)    in place of the deleted Section 10.l(j) described in (a) above, the following clause shall be inserted as a new Section 10.1(j): “to provide for additions of collateral security or guarantees for the Securities;”

(c)    Section 10.1(d) of the Original Indenture shall be amended by adding the following clause at the end: “; and to conform the terms and provisions of the Securities to the terms and provisions specified in the final prospectus supplement and accompanying prospectus relating to the Securities filed with the Commission under Rule 424(b);”;

(d)    Section 10.2 of the Original Indenture shall be amended by replacing the following clause “or change the redemption provisions,” with “or change the redemption provisions of the Securities in a manner that adversely affects Holders of the Securities,”; and

(e)    Section 10.2 of the Original Indenture shall be amended by replacing the following clause “or impair or adversely affect the right of any Securityholder to institute suit for the payment thereof or, if the Securities provide therefor, any right of repayment at the option of the Securityholder,” with “or impair the right to institute suit for the enforcement of any payment on or after the Final Maturity Date of the Senior Notes (or, in the case of redemption, on or after the Redemption Date),”.

Section 2.16.    Consolidation, Amalgamation, Merger and Sale. Only with respect to the Senior Notes issued hereunder, clause (a) of Section 11.1 of the Original Indenture is hereby amended with respect to the Senior Notes by deleting the text thereof in its entirety and inserting in its place the following:

“(a)    in case the Company shall consolidate or amalgamate with or merge into another Person or convey, transfer or lease its properties and assets as an entirety or substantially as an entirety to any Person, the Person formed by such consolidation or amalgamation or into which the Company is merged or the Person which acquires by conveyance or transfer, or which leases, the properties and assets of the Company as an entirety or substantially as an entirety shall be a Corporation, limited liability company or company organized, incorporated or continued and existing under the laws of the United States of America, any state thereof or the District of Columbia, Bermuda, the Cayman Islands or any other country (including under the laws of any state, province or other political subdivision thereof) which is on the date of this Indenture a member of the Organization for Economic Cooperation and Development, and shall expressly assume, by an indenture (or indentures, if at such time there is more than one Trustee) supplemental hereto, executed by the successor Person and delivered to the Trustee the due and punctual payment of the principal of, any premium and interest on and any Additional Amounts with respect to all the Securities and the performance of every obligation in this Indenture and the Outstanding Securities on the part of the Company to be performed or observed; and”

Section 2.17.    Unencumbered; No Rights of Set-Off.

(a)    In accordance with the Group Supervision Rules, the Senior Notes shall be unencumbered.

(b)    The Senior Notes will not in any way give rise to any rights of set-off, recoupments or counterclaims against any claims and obligations of the Company or any of the Company’s regulated operating subsidiaries to any Person in whose name the Senior Notes are registered or any creditor of the Company or any of the Company’s regulated operating subsidiaries.

(c)    By acceptance of the Senior Notes, each Holder of the Senior Notes will be deemed, to the extent permitted by law, to agree and acknowledge that (i) no security or encumbrance of any kind is, or will at any time be, provided by the Company or any of its affiliates

to secure the rights of Holders of the Senior Notes and (ii) the Senior Notes will not in any way give rise to any rights of set-off, recoupments or counterclaims against any claims and obligations of the Company or its regulated operating subsidiaries to any Person in whose names the Senior Notes are registered or any creditor of the Company or its regulated operating subsidiaries.

Section 2.18.    Appointment of Agents. The Trustee will initially be the paying agent for the Senior Notes (the “Paying Agent”).

Article III.

Section 3.1.    Ratification and Incorporation of the Original Indenture. As amended and supplemented hereby, the Original Indenture is in all respects ratified and confirmed, and the Original Indenture, as amended and supplemented by this Fifth Supplemental Indenture, shall be read, taken and construed as one and the same instrument.

Section 3.2.    Counterparts. This Fifth Supplemental Indenture may be executed in several counterparts, each of which shall be an original and all of which shall constitute but one and the same instrument. Notwithstanding Section 3.5 of the Original Indenture and as amended by this Section 3.2, the exchange of copies of this Fifth Supplemental Indenture, each Senior Note and of signature pages hereto and thereto (including the Trustee’s certificate of authentication of any Senior Note) by facsimile, PDF transmission or electronic signature (including those created or transmitted through a software platform or application) shall constitute effective execution and delivery of this Fifth Supplemental Indenture as to the parties hereto and of each Senior Note, and may be used in lieu of this Fifth Supplemental Indenture and each Senior Note signature pages for all purposes. The Trustee’s certificate of authentication of any Senior Note by manual, facsimile, PDF transmission or electronic signature (including those created or transmitted through a software platform or application) shall be conclusive evidence that the Senior Note so authenticated has been duly authenticated and delivered and that the Holder is entitled to the benefits of Original Indenture and this Fifth Supplemental Indenture.

Section 3.3.    Governing Law; Waiver of Jury Trial. This Fifth Supplemental Indenture shall be governed by and construed in accordance with the laws of the State of New York applicable to agreements made and performed in said state.

EACH OF THE PARTIES HERETO HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW, ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS FIFTH SUPPLEMENTAL INDENTURE, THE SENIOR NOTES OR THE TRANSACTIONS CONTEMPLATED HEREBY.

Section 3.4.    Headings. The Article and Section headings herein are for convenience only and shall not affect the construction hereof.

Section 3.5.    Trustee. The Trustee makes no representations as to the validity or sufficiency of this Fifth Supplemental Indenture. The recitals and statements herein are deemed to be those of the Company and not of the Trustee.

IN WITNESS WHEREOF, Aspen Insurance Holdings Limited has caused this Fifth Supplemental Indenture to be duly executed as of the date first above written.

IN WITNESS WHEREOF, the undersigned, being duly authorized, has executed this Fifth Supplemental Indenture as of the date first above written.

UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), TO ASPEN INSURANCE HOLDINGS LIMITED OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC (AND SUCH PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER, CEDE & CO., HAS AN INTEREST HEREIN.

UNLESS AND UNTIL THIS CERTIFICATE IS EXCHANGED IN WHOLE OR IN PART FOR SENIOR NOTES IN CERTIFICATED FORM, THIS CERTIFICATE MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE BY DTC TO A NOMINEE THEREOF OR BY A NOMINEE THEREOF TO DTC OR ANOTHER NOMINEE OF DTC OR BY DTC OR ANY SUCH NOMINEE TO A SUCCESSOR OF DTC OR A NOMINEE OF SUCH SUCCESSOR.

Aspen Insurance Holdings Limited, a company duly existing and organized under the laws of Bermuda (the “Company,” which term includes any successor corporation under the Indenture referred to on the reverse hereof), for value received, hereby promises to pay to CEDE & CO., or registered assigns, the Principal Amount shown above on the Scheduled Maturity Date or the Final Maturity Date shown above, and to pay interest thereon from the Original Issuance Date shown above, or from the most recent Interest Payment Date to which interest has been paid or duly provided for, semi annually in arrears on each Interest Payment Date as specified above (including the Scheduled Maturity Date or the Final Maturity Date), commencing on January 1, 2026, at the rate of 5.750% per annum until the principal hereof is paid or duly provided for. As provided in the Indenture, the Company under certain circumstances would be required to pay Additional Amounts to the Holders of the Senior Notes.

The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date (including the Scheduled Maturity Date or the Final Maturity Date) will, as provided in the Indenture, be paid to the Person in whose name this Senior Note is registered at the close of business on the Regular Record Date as specified above next preceding each Interest Payment Date. Any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date and may either be paid to the Person in whose name this Senior Note is registered at the close of business on a Special Record Date for the payment of such defaulted interest established by notice given by or on behalf of the Company to the Holders of the Senior Notes not less than 15 days prior to such Special Record Date, such Special Record Date to be not less than 10 days prior to the date for payment of such defaulted interest, or be paid at any time in any other lawful manner not inconsistent with the requirements of any securities exchange, if any, on which the Senior Notes shall be listed, and upon such notice as may be required by any such exchange, all as more fully provided in the Indenture.

Payments of interest on this Senior Note will include interest accrued to but excluding the respective Interest Payment Dates. Interest payments for this Senior Note shall be computed and paid on the basis of a 360-day year of twelve 30-day months. In the event that any date on which interest is payable on this Senior Note is not a Business Day, then payment of the interest payable on such date will be made on the next succeeding day that is a Business Day, with the same force and effect as if made on the date the payment was originally payable. A “Business Day” shall mean any day other than (i) a Saturday or Sunday, (ii) a day on which banking institutions in The City of New York are authorized or required by law or executive order to remain closed or (iii) a day on which the corporate trust office of the Trustee is closed for business.

Payment of the principal of and interest due on the Scheduled Maturity Date or Final Maturity Date of this Senior Note shall be made upon surrender of this Senior Note at the Corporate Trust Office of the Trustee. The principal of and interest on this Senior Note shall be paid in Dollars. Payments of principal of or interest will be made, subject to such surrender where applicable, at the option of the Company, by wire transfer to an account maintained by the Paying Agent, which will make payments to DTC. Thereafter, such payments will be credited to the DTC participants’ accounts that hold book-entry interests in the Global Notes and credited by such participants to the accounts of beneficial owners of the Senior Notes. The Company shall make all payments of principal, premium, if any, interest and any Additional Amounts with respect to Senior Notes held in certificated form to the Holder thereof by wire transfer of immediately available funds to the accounts specified by the Holders thereof or, if no such account is specified, by mailing a check to each such Holder’s registered address.

REFERENCE IS HEREBY MADE TO THE FURTHER PROVISIONS OF THIS SENIOR NOTE SET FORTH ON THE REVERSE HEREOF, WHICH FURTHER PROVISIONS SHALL FOR ALL PURPOSES HAVE THE SAME EFFECT AS IF SET FORTH AT THIS PLACE.

Unless the certificate of authentication hereon has been executed by the Trustee in accordance with the Indenture, this Senior Note shall not be entitled to any benefit under the Indenture or be valid or obligatory for any purpose.

IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed.

Dated:

This is one of the 5.750% Senior Notes due 2030 referred to in the within-mentioned Indenture.

Dated:

(reverse side of security)

This security is one of a duly authorized issue of debt securities of the Company (hereinafter called the “Securities”), all issued or to be issued under and pursuant to an Indenture, dated as of August 16, 2004 (the “Original Indenture”), between the Company and Deutsche Bank Trust Company Americas, as trustee (the “Trustee,” which term includes any successor trustee under the Indenture), as supplemented by the Fifth Supplemental Indenture dated as of June 13, 2025 (the “Fifth Supplemental Indenture,” and together with the Original Indenture, the “Indenture”), to which Indenture and all indentures supplemental thereto relating to this security (including, without limitation, the Fifth Supplemental Indenture, dated as of June 13, 2025, between the Company and the Trustee) reference is hereby made for a statement of the respective rights, limitation of rights, duties and immunities thereunder of the Company, the Trustee and the Holders of the Securities issued thereunder and of the terms upon which said Securities are, and are to be, authenticated and delivered. The Securities may be issued in one or more series, which different series may be issued in various aggregate principal amounts, may mature at different times, may bear interest at different rates and may otherwise vary as provided in the Indenture or any indenture supplemental thereto. This security is one of a series designated on the face as 5.750% Senior Notes due 2030 (the “Senior Notes”), initially limited in aggregate principal amount to $300,000,000, subject to increase as provided in Section 3.1 of the Indenture. Capitalized terms used herein for which no definition is provided herein shall have the meanings set forth in the Indenture.

While this Senior Note is represented by one or more global notes registered in the name of DTC or its nominee (the “Global Notes”), the Company will cause payments of principal of, premium, if any, and interest on this Senior Note to be made to DTC or its nominee, as the case may be, by wire transfer to the extent, in the funds and in the manner required by agreements with, or regulations or procedures prescribed from time to time by, DTC or its nominee, and otherwise in accordance with such agreements, regulations and procedures.

The Senior Notes will be senior unsecured obligations of the Company.

The Senior Notes will not have a sinking fund.

The Company shall have the right to redeem the Senior Notes under certain circumstances as set forth in Section 2.5 and Section 2.6, and subject to the conditions set forth in Section 2.7, of the Fifth Supplemental Indenture.

The Indenture also contains provisions for defeasance at any time of the entire indebtedness of the Senior Notes with respect thereto or of certain restrictive covenants of the Company with respect to the Senior Notes, in each case, upon compliance with certain conditions set forth in the Indenture.

If an Event of Default with respect to the Senior Notes shall occur and be continuing, the principal of the Senior Notes may be declared due and payable in the manner, with the effect and subject to the conditions provided in the Indenture.

The Indenture permits, with certain exceptions as therein provided, the amendment thereof and the modification of the respective rights and obligations of the Company and the rights of the Holders of the Senior Notes to be affected under the Indenture at any time by the Company and the Trustee with the consent of the Holders of not less than a majority in aggregate principal amount of the Senior Notes at the time Outstanding affected thereby.

The Indenture also contains provisions permitting the Holders of not less than a majority in principal amount of the Senior Notes at the time Outstanding, on behalf of the Holders of all Senior Notes, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such consent or waiver by the Holder of this Senior Note shall be conclusive and binding upon such Holder and upon all future Holders of this Senior Note and of any Senior Note issued upon the registration of transfer hereof or in exchange hereof or in lieu hereof, whether or not notation of such consent or waiver is made upon this Senior Note.

No reference herein to the Indenture and no provision of this Senior Note or of the Indenture shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay the principal of, premium, if any, and interest on and Additional Amounts, if any, in respect of this Senior Note at the times, place and rate, and in the coin or currency, herein prescribed.

As provided in the Indenture and subject to certain limitations therein set forth, the transfer of this Senior Note is registrable in the Security Register, upon surrender of this Senior Note for registration of transfer at the office or agency of the Company for such purpose, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Company and the Security Registrar and duly executed by, the Holder hereof or his attorney duly authorized in writing, and thereupon one or more new Senior Notes, of authorized denominations and of like tenor and for the same aggregate principal amount, will be issued to the designated transferee or transferees. No service charge shall be made for any such registration of transfer or exchange, but the Company may require payment of a sum sufficient to cover any tax or other governmental charge or certain other expenses payable in connection therewith.

Prior to due presentment of this Senior Note for registration of transfer, the Company, the Trustee and any agent of the Company or the Trustee may treat the Person in whose name this Senior Note is registered as the owner hereof for all purposes, whether or not this Senior Note be overdue, and neither the Company, the Trustee nor any such agent shall be affected by notice to the contrary.

The Senior Notes are issuable only in registered form without coupons in minimum denominations of $2,000 and any integral multiple of $1,000 in excess thereof. As provided in the Indenture and subject to certain limitations therein set forth, Senior Notes are exchangeable for a like aggregate principal amount of Senior Notes of a different authorized denomination, as requested by the Holder surrendering the same upon surrender of the Senior Notes to be exchanged at the office or agency of the Company.

By acceptance of this Senior Note, the Holder is deemed, to the extent permitted by law, to agree and acknowledge that (i) no security or encumbrance of any kind is, or will at any time be, provided by the Company or any of its affiliates to secure the rights of the Holder and (ii) this Senior Note will not in any way give rise to any rights of set-off, recoupments or counterclaims against any claims and obligations of the Company or its regulated operating subsidiaries to any Person in whose name this Senior Note is registered or any creditor of the Company or its regulated operating subsidiaries.

This Senior Note shall be governed by, and construed in accordance with, the laws of the State of New York applicable to agreements made and performed in said state.

The following abbreviations, when used in the inscription on the face of this instrument, shall be construed as though they were written out in full according to applicable laws or regulations:

TEN COM--as tenants in common UNIF GIFT MIN ACT- ___________Custodian_______

(Cust) (Minor)

under

Uniform Gifts to Minors Act ___

(State)

TEN ENT    as tenants by the entireties

JT TEN    as joint tenants with rights of

survivorship and not as tenants

in common

Additional abbreviations may also be used though not on the above list

FOR VALUE RECEIVED, the undersigned hereby sell(s) and transfer(s) unto (please insert Social Security or other identifying number of assignee)

____________________________________________________________________________

____________________________________________________________________________

the within Senior Note and all rights thereunder, hereby irrevocably constituting and appointing agent to transfer said Senior Note on the books of the Company with full power of substitution in the premises.

141 Front Street

Hamilton HM 19

Bermuda

Re:    Registration Statement on Form F-3

We refer to the Registration Statement on Form F-3, File No. 333-272650 (the “Registration Statement”), filed by Aspen Insurance Holdings Limited, an exempted company incorporated under the laws of Bermuda (the “Company”), with the Securities and Exchange Commission (the “SEC”) under the Securities Act of 1933, as amended (the “Securities Act”), which Registration Statement has been declared effective by the SEC. Pursuant to the Registration Statement, the Company is issuing $300,000,000 aggregate principal amount of its 5.750% Senior Notes due 2030 (the “Notes”). The Notes are being issued under an Indenture, dated as of August 16, 2004 (the “Base Indenture”), as amended and supplemented by a Fifth Supplemental Indenture, dated as of June 13, 2025 (the “Fifth Supplemental Indenture” and, together with the Base Indenture, the “Indenture”), each between the Company and Deutsche Bank Trust Company Americas, as trustee (the “Trustee”). The Notes are to be sold by the Company pursuant to an underwriting agreement, dated June 10, 2025 (the “Underwriting Agreement”), among the Company and Citigroup Global Markets Inc., Lloyds Securities Inc. and HSBC Securities (USA) Inc., as representatives of the several underwriters named therein.

This opinion letter is being delivered in accordance with the requirements of Item 601(b)(5) of Regulation S-K under the Securities Act.

We have examined (i) the Registration Statement, (ii) the Indenture, (iii) the Underwriting Agreement, (iv) the Notes in global form and (v) certain resolutions of the Board of Directors of the Company (the “Board”) and the pricing committee thereof established by the Board, each as certified by the Secretary of the Company on the date hereof as being true, complete and correct, relating to, among other things, the execution of the Underwriting Agreement and the issuance and sale of the Notes. We have also examined originals, or copies of originals certified to our satisfaction, of such agreements, documents, certificates and statements of the Company and other corporate documents and instruments, and have examined such questions of law, as we have considered relevant and necessary as a basis for this opinion letter. We have assumed the authenticity of all documents submitted to us as originals, the genuineness of all signatures, the legal capacity of all persons and the conformity with the original documents of any copies thereof submitted to us for examination. As to facts relevant to the opinions expressed herein, we have relied without independent investigation or verification upon, and

assumed the accuracy and completeness of, certificates, letters and oral and written statements and representations of public officials and officers and other representatives of the Company.

Based on and subject to the foregoing and the other limitations, qualifications and assumptions set forth herein, we are of the opinion that the Notes will constitute valid and binding obligations of the Company when the Notes are duly executed by duly authorized officers of the Company and duly authenticated by the Trustee, all in accordance with the provisions of the Indenture, and delivered to the purchasers thereof against payment of the agreed consideration therefor in accordance with the Underwriting Agreement.

Our opinion is subject to bankruptcy, insolvency, reorganization, moratorium, fraudulent conveyance, fraudulent transfer and other similar laws relating to or affecting creditors’ rights generally, including, to the extent applicable, the rights or remedies of creditors of a “financial company” (as defined in Section 201 of the Dodd-Frank Wall Street Reform and Consumer Protection Act), or the affiliates thereof, and to general equitable principles (regardless of whether considered in a proceeding in equity or at law), including concepts of commercial reasonableness, good faith and fair dealing and the possible unavailability of specific performance or injunctive relief. Our opinion is also subject to (i) provisions of law which may require that a judgment for money damages rendered by a court in the United States of America be expressed only in United States dollars, (ii) requirements that a claim with respect to any debt securities or other obligations that are denominated or payable other than in United States dollars (or a judgment denominated or payable other than in United States dollars in respect of such claim) be converted into United States dollars at a rate of exchange prevailing on a date determined pursuant to applicable law and (iii) governmental authority to limit, delay or prohibit the making of payments outside of the United States of America or in a foreign currency.

With respect to each instrument or agreement referred to herein or otherwise relevant to the opinions or other statements set forth herein (each, an “Instrument”), we have assumed that (i) each party to such Instrument (if not a natural person) was duly organized or formed and was at all relevant times and is validly existing and in good standing under the laws of its jurisdiction of organization or formation and had at all relevant times and has full right, power and authority to execute, deliver and perform its obligations under such Instrument and (ii) such Instrument has been duly authorized, executed and delivered by each party thereto. Furthermore, we have also assumed that the execution, delivery and performance by the Company of the Underwriting Agreement and the Indenture did not, do not and will not violate or contravene any law, rule or regulation of Bermuda or any governmental authorities of or within Bermuda or any provisions of the Memorandum of Association or Third Amended and Restated Bye-Laws (or other organizational documents) of the Company or require any consents, approvals or authorizations from, or any registrations, declarations or filing with, Bermuda or any governmental authorities of or within Bermuda (except such as have been obtained and are in full force and effect) or any applicable insurance authorities that have jurisdiction over the Company or its business.

This opinion letter is limited to the laws of the State of New York (excluding the securities laws of the State of New York). We express no opinion as to the laws, rules or regulations of any other jurisdiction, including, without limitation, the federal laws of the United States of America or any state securities or blue sky laws or the laws of Bermuda.

We hereby consent to the filing of this opinion letter as an Exhibit to the Registration Statement and to all references to our Firm included in or made a part of the Registration Statement. In giving such consent, we do not thereby admit that we are in the category of persons whose consent is required under Section 7 of the Securities Act.

Very truly yours,

/s/ Sidley Austin LLP

Dear Addressee

We have been asked to provide this legal opinion to you with regard to the laws of Bermuda in connection with the offering pursuant to the Registration Statement (as defined in Schedule 1) by Aspen Insurance Holdings Limited (the "Company") of its US$300,000,000 aggregate principal amount of 5.750% Senior Notes due 2030 (the “Notes”) pursuant to the Base Indenture (as defined in Schedule 1) and as supplemented by the Fifth Supplemental Indenture (as defined in Schedule 1).

For the purposes of giving this opinion, we have examined and relied upon the originals, copies or translations of the documents listed in Schedule 1.

In giving this opinion we have relied upon the assumptions set out in Schedule 2, which we have not independently verified.

We are Bermuda Barristers and Attorneys and express no opinion as to any laws other than the laws of Bermuda in force and as interpreted at the date of this opinion.  We have not, for the purposes of this opinion, made any investigation of the laws, rules or regulations of any other jurisdiction.  Except as explicitly stated herein, we express no opinion in relation to any representation or warranty contained in the Notes or the Documents nor upon matters of fact or the commercial terms of the transactions contemplated by the Notes and the Documents.

Based upon the foregoing examinations and assumptions and upon such searches as we have conducted and having regard to legal considerations which we consider relevant, and subject to the qualifications set out in Schedule 3, and under the laws of Bermuda, we give the following opinions in relation to the matters set out below.

1.The Company is an exempted company duly incorporated under the Companies Act, 1981 (as amended) (the "Companies Act") and validly exists as a company limited by shares in Bermuda. Based solely on the Certificate of Compliance referred to in Schedule 1, the Company is in good standing under the laws of Bermuda.

2.The Company has full corporate power and authority to execute and deliver the Documents to which it is a party, to issue the Notes and to perform its obligations under the Documents and the Notes.

3.The issue of the Notes and the execution of the Documents to which the Company is a party have been duly authorised by the Company and the Documents have been duly executed by the Company. The Transaction Documents to which the Company is a party, when delivered, and the Notes, when issued and authenticated, will constitute the legal, valid and binding obligations of the Company enforceable in accordance with their respective terms.

4.The issue of the Notes and the execution (where applicable), delivery and performance of the Transaction Documents to which the Company is a party, the consummation of the transactions contemplated thereby and the compliance by the Company with the terms and provisions thereof do not:

(a)contravene any law, or public rule or regulation of Bermuda applicable to the Company which is currently in force; or

(b)contravene the Memorandum and Bye-laws (as defined in Schedule 1).

5.The law (if any) chosen in each of the Notes and the Documents to which the Company is a party to govern their interpretation would be upheld as a valid choice of law in any action on that Document or Note in the courts of Bermuda (the "Courts" and each a "Court").

6.Based solely on a search of:

(a)the entries and filings shown in respect of the Company on the files of the Company maintained in the Register of Companies (the "Register") at the office of the Registrar of Companies (the "Registrar") conducted on the Registry Search Date (as defined in Schedule 1); and

(b)the records in respect of the Company in the Court Database (as defined in Schedule 1) conducted on the Court Search Date (as defined in Schedule 1) (the "Supreme Court Search"),

(together the "Searches") there are no judgments, actions, suits or proceedings pending against the Company before the Courts and the Searches do not reveal any steps having been taken in Bermuda for the appointment of a receiver or liquidator to, or for the winding-up, dissolution, reconstruction or reorganisation of the Company (to the extent that such steps would result in a filing with the Registrar or the Courts and such filing has been made).

This opinion is limited to the matters referred to herein and shall not be construed as extending to any other matter or document not referred to herein.  This opinion is given solely for your benefit and the benefit of your legal advisers acting in that capacity in relation to this transaction and may not be relied upon by any other person without our prior written consent.

We understand that the Company wishes to file this opinion as an exhibit to the Registration Statement as Exhibit 5.2 and to reference this firm under the caption “Legal Matters” in the prospectus contained in the Registration Statement, and we hereby consent thereto. In giving such consent, we do not thereby admit that we are within the category of persons whose consent is required under Section 7 of the Securities Act (as defined in Schedule 1) or the rules and regulations of the Commission thereunder.

This opinion shall be construed in accordance with the laws of Bermuda.

Yours faithfully

/s/ Walkers (Bermuda) Limited

1.The Certificate of Incorporation as issued on 23 May 2002, the Certificate of Incorporation on Change of Name as issued on 26 November 2002, Memorandum of Association as registered on 23 May 2002 (the "Memorandum of Association"), Third Amended and Restated Bye-laws (the "Bye-laws" and together the "Memorandum and Bye-laws") of the Company in the form attached to the Secretary's Certificate dated 3 June 2025 (the "Secretary Certificate") provided to us by the Company's Secretary, Register of Members, Register of Directors and Officers, in each case of the Company, copies of which have been provided to us in the Secretary's Certificate (together, the "Company Records")

2.The public records of the Company on the Register, examined on 12 June 2025 (the "Registry Search Date").

3.The records of proceedings appearing in the Supreme Court Cause and Judgment Book (the "Book"), and available for inspection at the Registry of the Supreme Court (the "Court Registry"), as set out in a database of issued proceedings maintained by us for the period from 1 January 2017 to 10 June 2025 (the "Court Database"), examined on 12 June 2025 (the "Court Search Date" and the Court Search Date and the Registry Search Date each a "Search Date").

4.A Certificate of Compliance dated 12 June 2025 issued by the Registrar in relation to the Company (the "Certificate of Compliance").

5.A certified extract of minutes of a meeting of the board of directors of the Company held on 15 May 2025 (the "Board Resolutions"), and a certified extract of the resolutions of the pricing committee of the Company approved by the board dated 15 May 2025 (the Board Resolutions, together with the resolutions of the pricing committee, the "Resolutions").

6.An indenture dated as of 16 August 2004 as amended and supplemented by the fifth supplemental indenture dated 13 June 2025 (the "Base Indenture") between the Company and Deutsche Bank Trust Company Americas, as trustee (the "Trustee");

7.Executed copies of the following:

(a)a fifth supplemental indenture dated 13 June 2025 between the Company and the Trustee; and

(b)an underwriting agreement dated 10 June 2025 made among the Company, Citigroup Global Markets Inc., Lloyds Securities Inc. and HSBC Securities (USA) Inc. as representatives of the several underwriters named in Schedule I thereto.

The documents listed in paragraphs 7(a) and 7(b) above inclusive are collectively referred to in this opinion as the "Documents" and the Documents together with the Base Indenture are collectively the "Transaction Documents".

8.The global securities representing the Notes.

9.The Registration Statement on Form F-3 (File No. 333-272650) (the "Registration Statement") filed with the Securities and Exchange Commission under the U.S. Securities Act of 1933, as amended (the "Securities Act"), as amended through the date hereof.

10.The Preliminary Prospectus Supplement dated 9 June 2025 and accompanying base prospectus dated 26 June 2023 (the "Base Prospectus") issued by the Company in relation to the issue of the Notes (together, the "Preliminary Prospectus Supplement") and the Final Prospectus Supplement dated 10 June 2025 (the "Final Prospectus Supplement") and accompanying Base Prospectus, issued by the Company in relation to the issue of the Notes.

1.There are no provisions of the laws of any jurisdiction outside Bermuda which would be contravened by the execution or delivery of the Transaction Documents or the issue and offering of the Notes and, insofar as any obligation expressed to be incurred under the Transaction Documents or the Notes is to be performed in or is otherwise subject to the laws of any jurisdiction outside Bermuda, its performance will not be illegal by virtue of the laws of that jurisdiction.

2.The Transaction Documents and the Notes are within the capacity, power and legal right of, and have been or will be duly authorised, executed and delivered by, each of the parties thereto (other than the Company).

3.The Transaction Documents and the Notes constitute or, when executed and delivered or issued and authenticated, will constitute the legal, valid and binding obligations of each of the parties thereto enforceable in accordance with their terms as a matter of the laws of all relevant jurisdictions (other than Bermuda).

4.The choice of the laws of the jurisdiction selected to govern each of the Transaction Documents and the Notes has been made in good faith and will be regarded as a valid and binding selection which will be upheld in the courts of that jurisdiction and all relevant jurisdictions (other than Bermuda).

5.All authorisations, approvals, consents, licences and exemptions required by, and all filings and other steps required of each of the parties to the Transaction Documents and the Notes outside Bermuda to ensure the legality, validity and enforceability of the Transaction Documents and the Notes have been or will be duly obtained, made or fulfilled and are and will remain in full force and effect and any conditions to which they are subject have been satisfied.

6.All conditions precedent, if any, contained in the Transaction Documents have been or will be satisfied or waived.

7.On the date of execution of the Transaction Documents, no party to the Transaction Documents was resident in, or was engaged in or carrying on any trade or business in or from, Bermuda (subject, in the case of the Company, to the exceptions listed in section 129(1)(e)(i)-(viii) of the Companies Act).

8.No director of the Company has an interest in, other than as disclosed in the Resolutions:

(a)any of the Transaction Documents or the Notes; or

(b)any person that is a party to any of the Transaction Documents or the Notes.

9.The board of directors of the Company considers (acting honestly and in good faith) the execution of the Transaction Documents and the issue of the Notes and the transactions contemplated thereby to be in the best interests of the Company.

10.Each transaction entered into pursuant to the Transaction Documents and the Notes is entered into in good faith and for full value and will not have the effect of preferring one creditor over another.

11.There is no matter affecting the authority of the directors of the Company to effect entry by the Company into the Transaction Documents or the Notes, not disclosed by the Memorandum and Bye-laws or the Resolutions, which would have an adverse implication in relation to the opinions expressed herein.

12.The Company was on the date of issue of the Notes and execution of the Transaction Documents to which it is a party able to pay its debts as they became due from its own moneys, and any disposition or settlement of property effected by any of the Notes or the Transaction Documents is made in good faith and for valuable consideration and at the time of each disposition of property by the Company pursuant to the Notes and the Transaction Documents the Company will be able to pay its debts as they become due from its own moneys.

13.The originals of all documents examined in connection with this opinion are authentic.  The signatures, initials and seals on the Transaction Documents are genuine and are those of a person or persons given power to execute the Notes and the Transaction Documents under the Resolutions or any power of attorney given by the Company to execute the Transaction Documents.  All documents purporting to be sealed have been so sealed.  All copies are complete and conform to their originals. Any translations are a complete and accurate translation of the original document they purport to translate.  The Notes and the Transaction Documents conform in every material respect to the latest drafts of the same produced to us and, where provided in successive drafts, have been marked up to indicate all changes to such Notes and Transaction Documents.

14.Any documents or certificates executed as a deed were executed as a single physical document (whether in counterpart or not) in full and final form.

15.The Memorandum and Bye-laws reviewed by us are the memorandum of association and bye-laws of the Company and are in force at the date hereof.

16.The Certificate of Compliance and the results of the Searches are complete, true and accurate as at the date of this opinion and, furthermore, such Searches were complete, true and accurate as at the Search Date and disclose:

(c)in the case of the Register, all matters which have been filed for registration in respect of the Company at the offices of the Registrar; and

(d)in the case of the Courts, all actions, suits and proceedings pending against the Company before the Courts.

17.The Company Records are complete and accurate and all matters required by law and the Memorandum and Bye-laws to be recorded therein are completely and accurately so recorded.

18.There are no records of the Company (other than the Company Records), agreements, documents or arrangements other than the documents expressly referred to herein as having been examined by us which materially affect, amend or vary the transactions envisaged in the Notes and Transaction Documents or restrict the powers and authority of the directors of the Company in any way or which would affect any opinion given herein.

19.The Resolutions were duly adopted at a duly convened and quorate meeting of the board of directors of the Company and such meeting was held and conducted in accordance with the Memorandum and Bye-laws.

20.The Resolutions and any power of attorney given by the Company to execute the Transaction Documents remain in full force and effect and have not been revoked or varied.

21.No resolution voluntarily to wind up the Company has been adopted by the members of the Company and no event of a type which is specified in the Memorandum and Bye-laws as giving rise to the winding up of the Company (if any) has in fact occurred.

22.As a matter of all relevant laws (other than the laws of Bermuda), any power of attorney given by the Company to execute the Transaction Documents has been duly executed by the Company and constitutes the persons named therein as the duly appointed attorney of the Company with such authority as is specified therein.

23.As a matter of all relevant laws (other than the laws of Bermuda) none of the Transaction Documents constitutes a security interest.

24.The Company is not a sovereign entity of any state and is not a subsidiary, direct or indirect of any sovereign entity or state.

1.The term "enforceable" and its cognates as used in this opinion means that the obligations assumed by any party under the Notes and the Transaction Documents are of a type which the Courts enforce.  This does not mean that those obligations will necessarily be enforced in all circumstances in accordance with their terms.  In particular:

(e)enforcement of obligations and the priority of obligations may be limited by bankruptcy, insolvency, liquidation, reorganisation, readjustment of debts or moratorium and other laws of general application relating to or affecting the rights of creditors or by prescription or lapse of time;

(f)enforcement may be limited by general principles of equity and, in particular, the availability of certain equitable remedies such as injunction or specific performance of an obligation may be limited where a Court considers damages to be an adequate remedy;

(g)claims may become barred under statutes of limitation or may be or become subject to defences of set-off, counterclaim, estoppel and similar defences;

(h)where obligations are to be performed in a jurisdiction outside Bermuda, they may not be enforceable in Bermuda to the extent that performance would be illegal under the laws of, or contrary to the public policy of, that jurisdiction;

(i)in the case of an insolvent liquidation of the Company, it is likely that the liquidator will convert the Company's liabilities into the principal currency in which the Company conducts its business at the exchange rate prevailing on the date on which the winding up petition is filed;

(j)to the extent that any provision of the Transaction Documents or the Notes is adjudicated to be penal in nature, it will not be enforceable in the Courts; in particular, the enforceability of any provision of the Transaction Documents or the Notes that is adjudicated to constitute a secondary obligation which imposes a detriment on the contract-breaker out of all proportion to any legitimate interest of the innocent party in the enforcement of the primary obligation may be limited;

(k)to the extent that the performance of any obligation arising under the Notes or the Transaction Documents would be fraudulent or contrary to public policy, it will not be enforceable in the Courts;

(l)a Court will not necessarily award costs in litigation in accordance with contractual provisions in this regard; and

(m)the effectiveness of terms in the Notes or the Transaction Documents excusing any party from a liability or duty otherwise owed or indemnifying that party from the consequences of incurring such liability or breaching such duty shall be construed in accordance with, and shall be limited by, applicable law, including generally applicable rules and principles of common law and equity.

2.A certificate, determination, calculation or designation of any person in the Notes or of any party to the Transaction Documents as to any matter provided therein might be held by a Court not to be conclusive, final and binding, notwithstanding any provision to that effect therein contained, for example if it could be shown to have an unreasonable, arbitrary or improper basis or in the event of manifest error.

3.If any provision of the Notes or the Transaction Documents is held to be illegal, invalid or unenforceable, severance of such provision from the remaining provisions will be subject to the discretion of the Courts notwithstanding any express provisions in this regard.

4.We express no opinion upon any provisions in the Memorandum and Bye-laws or any document which contains a reference to any law or statute that is not a Bermuda law or statute.

5.We express no opinion upon the effectiveness of any clause of the Transaction Documents which provides that the terms of such Document may only be amended in writing.

6.Notwithstanding any purported date of execution in any of the Notes or the Transaction Documents, the rights and obligations therein contained take effect only on the actual execution and delivery thereof but the terms of the Notes or the Transaction Documents may provide that they have retrospective effect as between the parties thereto alone or between the Company and the holder of the Notes, as the case may be.

7.The obligations of the Company may be subject to restrictions pursuant to United Nations sanctions and/or measures extended to Bermuda by statutory instrument.

8.Our opinion as to good standing is based solely upon receipt of the Certificate of Compliance, which confirms only that the Company has neither failed to make any filing with any Bermuda governmental authority nor failed to pay any Bermuda government fee or tax, which might make it liable to be struck off the Register.

9.Searches of the Register at the offices of the Registrar and of the Book at the Court Registry are not conclusive and it should be noted that the Register and the Book do not reveal:

(a)details of matters which have been lodged for filing or registration which as a matter of best practice of the Registrar or the Court Registry would have or should have been disclosed on the public file or the Book, as the case may be, but for whatever reason have not actually been filed or registered or are not disclosed or which, notwithstanding filing or registration, at the date and time the search is concluded are for whatever reason not disclosed or do not appear on the public file or the Book;

(b)details of matters which should have been lodged for filing or registration with the Registrar or at the Court Registry but have not been lodged for filing or registration at the date the search is concluded;

(c)whether an application to the Supreme Court of Bermuda for a winding-up petition or for the appointment of a receiver or manager has been prepared but not yet been presented or has been presented but does not appear in the Book at the date and time the search is concluded;

(d)whether any arbitration or administrative proceedings are pending or whether any proceedings are threatened, or whether any arbitrator has been appointed; or

(e)whether a receiver or manager has been appointed privately pursuant to the provisions of a debenture or other security, unless notice of the fact has been entered in the register of charges in accordance with the provisions of the Companies Act.

10.All powers of attorney granted by the Company in the Transaction Documents or the Notes must be duly executed as deeds or under seal by persons authorised to do so if governed by the laws of Bermuda.

11.We render no opinion as to the specific enforcement as against the Company of covenants granted by the Company to do or to omit to do any action or other matter which is reserved by applicable law or the Company's constitutional documents to the members of the Company or to any other person.

12.Certain of the Transaction Documents contain provisions the intention of which is to restrict the ability of certain parties to, inter alia, petition for or take any other step in relation to the winding up of the Company.  Such Transaction Documents are not governed by the laws of Bermuda.  The Courts would hear any petition to wind up the Company brought in breach of any non-petition provisions.  However, subject to any applicable provisions of the Transaction Documents to the contrary, the Company could seek to restrain a threatened breach of such provision by way of an application to the Courts for an injunction.  An injunction is, however, a discretionary remedy, the grant of which is subject to a number of factors, including whether such grant would be contrary to public policy.

13.Where a document provides for an exclusive or non-exclusive jurisdiction clause submitting (or permitting the submission) to the jurisdiction of the Courts, a Court may decline to accept jurisdiction in any matter where:

(f)it determines that some other jurisdiction is a more appropriate or convenient forum;

(g)another court of competent jurisdiction has made a determination in respect of the same matter; or

(h)litigation is pending in respect of the same matter in another jurisdiction.

Proceedings may be stayed in Bermuda if concurrent proceedings in respect of the same matter are or have been commenced in another jurisdiction.

14.Where a document provides for an exclusive jurisdiction clause submitting to the jurisdiction of a court other than the Courts, notwithstanding any provision of the document providing for the exclusive jurisdiction of a court other than the Courts, the Court may, if it is satisfied that it is just and equitable to allow such proceedings to continue in Bermuda:

(i)decline to stay proceedings issued in contravention of such provision; or

(j)grant leave to serve Bermudian proceedings out of Bermuda.

15.The priority and extent of security over the assets of the Company may be affected by a merger, amalgamation or consolidation of the Company.

16.We express no opinion on and our opinions are subject to the effect, if any, of any provisions of any Document or the Notes that relies upon financial or numerical computation.

17.We express no opinion as to the enforceability of any provision of the Transaction Documents which provides for the payment of a specified rate of interest on the amount of a judgment after the date of judgment or which purports to fetter the statutory powers of the Company.

18.A receiver or manager of the Company appointed pursuant to the Transaction Documents is required to give notice to the Registrar of Companies in Bermuda within seven days of the date of order or appointment in accordance with section 60 of the Companies Act and in the form provided by the Companies (Forms) Rules 1982. On payment of the appropriate fee, the Registrar of Companies shall enter the fact of this appointment in the register of charges maintained pursuant to Part V of the Companies Act. Such a receiver or manager must be duly qualified pursuant to and comply with the provisions of Part XIV of the Companies Act.

19.The powers granted to a receiver or manager under the Transaction Documents will be ineffective or limited to the extent that they conflict with or purport to give the receiver or manager powers which are by statue reserved exclusively to the board of directors of the Company or the members of the Company, such as the power to use the common seal and power to change the registered office. The exercise of such powers will also be subject to the discretion of the Courts which is wide and exercisable on general equitable grounds.