Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 56

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 56
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 payable in respect of the issue of the notes; and

(c) certificates evidencing the notes, in registered form, to which title is not transferable by delivery, will not attract Bermuda stamp duty.

(d) The Issuer has been incorporated with limited liability under the laws of Bermuda as an exempted company and, as such, has obtained an undertaking from the Minister of Finance of Bermuda in the following form:

#### BERMUDA

#### TAX ASSURANCE

#### WHEREAS
the Minister of Finance (“the Minister”), pursuant to section 2 of the Exempted Undertakings Tax Protection Act 1966, is authorised to enter into an arrangement with any exempted undertaking upon application.

#### WHEREAS
such undertakings may be given an assurance that in the event of there being enacted in Bermuda any legislation imposing tax computed on profits or income or computed on any capital asset, gain or appreciation, or any tax in the nature of estate duty or inheritance tax, then the imposition of any tax described herein shall not be applicable to such undertakings or to any of its operations or the shares, debentures or other obligations of the said undertakings.

<div align='center'>S-32</div>

#### THEREFORE
the Minister, upon application, hereby grants the aforementioned assurance to:

#### Aspen Insurance Holdings Limited
<div align='center'>(“the Undertaking”)</div>

#### PROVIDED THAT
this assurance shall not be construed so as to:

(i) prevent the application of any such tax or duty to such persons as are ordinarily resident in these Islands; and

(ii) prevent the application of any tax payable in accordance with the provisions of the Land Tax Act 1967 or otherwise payable in relation to the land leased to the Undertaking.

#### THIS TAX ASSURANCE
shall be in effect until the

#### 31st
day of

#### March 2035
.”

Bermuda has a tax treaty with the United States, which was signed in 1986 and came into force in 1988. The agreement applies only to federal income taxes and excise taxes in relation to insurance business. In addition, Bermuda has entered into a tax information exchange agreement with the United States and has entered into tax information exchange agreements with certain other jurisdictions pursuant to the Organisation for Economic Co-operation and Development Standard for Automatic Exchange of Financial Account Information – Common Reporting Standards.

#### Bermuda Corporate Income Tax Act (“CIT Act”)
As a result of changes made by the CIT Act, the assurance referenced above