Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 21

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 21
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                                                              |     | $                                       | 3,190.5 |     | $           | 3,190.5 |
| Total Capitalization(5)                                                                                                                                                                                                 |     | $                                       | 3,490.5 |     | $           | 3,490.5 |

__________________

(1) We intend to use the net proceeds from this offering, together with cash on hand, to repay the indebtedness outstanding under the Term Loan Credit Agreement.

(2) Does not reflect letters of credit outstanding under our letter of credit facilities and revolving credit facility.

(3) As of March 31, 2025, we had undrawn commitments available for borrowings under our revolving credit facility of up to $300.0 million (there were no outstanding letters of credit under such facility as of such date). We have the option to increase the aggregate amount of our revolving credit facility by up to $100.0 million, subject to certain conditions. Aspen Holdings and certain of its direct or indirect subsidiaries are the borrowers under such revolving credit facility and Aspen Holdings has guaranteed the borrowings of any such subsidiary borrowers under our revolving credit facility.

(4) The liquidation preference is reflected net of issuance costs.

(5) Total capitalization equals total long-term debt obligations plus total shareholders’ equity.

<div align='center'>S-13</div>

### DESCRIPTION OF NOTES
The following summary of the particular terms of the notes we are offering supplements the description of the general terms and provisions of the debt securities set forth under “Description of the Debt Securities” beginning on page 29 in the accompanying prospectus. The accompanying prospectus contains a detailed summary of additional provisions of the notes. The following description replaces the description of the debt securities in the accompanying prospectus to the extent of any inconsistency. Terms used in this prospectus supplement that are otherwise not defined will have the meanings given to them in the accompanying prospectus. This summary is not complete and we encourage you to read the accompanying prospectus and the senior notes indenture referred to below, a copy of which is filed as an exhibit to the registration statement described in the accompanying prospectus.

As used in this “Description of Notes” section, “we,” “our,” “us” and “Aspen Holdings” mean Aspen Insurance Holdings Limited and do not include its subsidiaries.

#### General
The 5.750% Senior Notes due 2030 offered by this prospectus supplement will constitute a new, single series of senior debt securities (as described in the accompanying prospectus