Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 77

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 77
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 supplement is delivered, upon written or oral request and at no cost to such person, a copy of any or all of the information that has been incorporated by reference in this prospectus supplement but not delivered with this prospectus supplement. You may request a copy of such information by writing or telephoning us at:

<div align='center'>Aspen Insurance Holdings Limited

Attention: Company Secretary

141 Front Street

Hamilton HM19

Bermuda

(441) 295-8201</div>

You should rely only upon the information provided in this prospectus supplement or incorporated in this document by reference. We have not authorized anyone to provide you with different information. You should not assume that the information in this prospectus supplement, including any information incorporated by reference, is accurate as of any date other than that on the front cover of the document.

<div align='center'>S-45</div>

### PROSPECTUS
<div align='center'>$600,000,000</div>

### ASPEN INSURANCE HOLDINGS LIMITED
<div align='center'>Preference Shares; Depositary Shares; Senior or Subordinated Debt Securities</div>

We may, from time to time, offer and sell:

• preference shares;

• depositary shares representing preference shares; and

• senior or subordinated debt securities.

We may offer, from time to time, in one or more offerings or series, together or separately, up to $600,000,000 of our preference shares, depositary shares representing preference shares or debt securities. We will describe in a prospectus supplement, which must accompany this prospectus (this “Prospectus”), the type and amount of a series of securities we are offering and selling, as well as the specific terms and public offering prices of these securities. Such prospectus supplement may also add, update or change information contained in this Prospectus. You should read this Prospectus and any accompanying prospectus supplement carefully before you invest in these securities.

We may offer securities in amounts, at prices and on terms to be determined at the time of offering. We may sell these securities to or through underwriters and also to other purchasers or through agents. If any agents or underwriters are involved in the sale of any securities, the names of the underwriters or agents and the specific terms of a plan of distribution will be stated in an accompanying prospectus supplement.

Our 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (the “5.95% Preference Shares”)