Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 2

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 2
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     | 29 |
| CERTAIN PROVISIONS APPLICABLE TO THE SENIOR DEBT SECURITIES                                    |     | 40 |
| CERTAIN PROVISIONS APPLICABLE TO THE SUBORDINATED DEBT SECURITIES                              |     | 42 |
| PLAN OF DISTRIBUTION                                                                           |     | 44 |
| TAXATION                                                                                       |     | 47 |
| WHERE YOU CAN FIND MORE INFORMATION                                                            |     | 48 |
| INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE                                                |     | 48 |
| EXPENSES ASSOCIATED WITH THE REGISTRATION                                                      |     | 50 |
| LEGAL MATTERS                                                                                  |     | 51 |
| EXPERTS                                                                                        |     | 51 |
| ENFORCEMENT OF CIVIL LIABILITIES UNDER UNITED STATES FEDERAL SECURITIES LAWS AND OTHER MATTERS |     | 52 |
| AUTHORIZED REPRESENTATIVE                                                                      |     | 54 |

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### ABOUT THIS PROSPECTUS SUPPLEMENT
This prospectus supplement and the accompanying prospectus relate to the offer and sale by us of the notes. You should rely only on the information contained or incorporated by reference into this prospectus supplement and the accompanying prospectus. We have not, and the underwriters have not, authorized any other person to provide you with different information. If anyone provides you with different or inconsistent information, you should not rely on it. Neither we nor the underwriters are making an offer to sell the notes in any jurisdiction where the offer or sale is not permitted. You should assume that the information contained in this prospectus supplement, the accompanying prospectus and the documents incorporated by reference is accurate only as of their respective dates. Our business, results of operations, financial condition and prospects may have changed since those dates.

This prospectus supplement contains basic information about us and the notes. This prospectus supplement may add, update or change information contained in or incorporated by reference into the accompanying prospectus. In addition, the information incorporated by reference into the accompanying prospectus may have added, updated or changed information in the accompanying prospectus. If information in this prospectus supplement is inconsistent with any information in the accompanying prospectus or any information incorporated therein by reference, this prospectus supplement will apply and will supersede such information. It is important for you to read and consider all information contained or incorporated by reference in this prospectus supplement and the accompanying prospectus in making your investment decision. You