Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 9

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 9
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Our principal executive offices are located at 141 Front Street, Hamilton HM 19, Bermuda. Our telephone number is (441) 295-8201, and our website is www.aspen.co. None of the information contained on the website is part of this prospectus supplement.

For further information regarding Aspen Holdings, including financial information, you should refer to our recent filings with the SEC. See “ Where You Can Find More Information ” and “ Incorporation of Certain Documents by Reference ” in this prospectus supplement for more information.

#### Recent Developments
On May 9, 2025, we completed our initial public offering, pursuant to which certain of our shareholders managed by affiliates of Apollo Global Management, Inc. (the “selling shareholders”) sold 13,250,000 of our Class A ordinary shares, par value $0.001 (“ordinary shares”), at a public offering price of $30.00 per share. Subsequently, on May 13, 2025, the selling shareholders sold 1,987,500 ordinary shares in connection with the full exercise by the underwriters of their 30-day option to purchase additional ordinary shares at a public offering price of $30.00 per share. We did not receive any of the proceeds from the sale of ordinary shares by the selling shareholders. The ordinary shares began trading under the ticker symbol “AHL” on the NYSE on May 8, 2025.

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The Offering The following summary is provided solely for your convenience. The summary is not intended to be complete. You should read the full text and more specific details contained elsewhere in this prospectus supplement. For a more detailed description of the notes, see “ Description of Notes .”

| Issuer        |     | Aspen Insurance Holdings Limited, a Bermuda holding company.                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                    |
| Notes Offered |     | $              aggregate principal amount of              % Senior Notes due 20           .                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                     |
| Maturity Date |     | (i)              , 20             (the “Scheduled Maturity Date”), if, on the Scheduled Maturity Date, the BMA Redemption Requirements (as defined herein) 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 (as defined herein) after the