Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 10

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 10
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| Trustee                            |     | Deutsche Bank Trust Company Americas                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
| Additional Notes                   |     | We may, without the consent of the holders of any of the notes, issue additional notes from time to time after this offering having terms identical in all respects to the notes offered by this prospectus supplement, except for the issue date, the issue price, interest accrued prior to the issue date of the additional notes and the first interest payment date, as described under “Description of Notes—General.”                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                      |
| Conflicts of Interest              |     | As described under “Use of Proceeds,” 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 under which affiliates of certain of the underwriters in this offering are lenders. Because at least 5% of the net proceeds from this offering will be used to repay the indebtedness outstanding under the Term Loan Credit Agreement owed to one or more individual underwriters and their affiliates, this offering will be conducted in accordance with Rule 5121 of the Financial Industry Regulatory Authority, Inc. (“FINRA”). Any underwriter that has a “Conflict of Interest” within the meaning of FINRA Rule 5121 will not confirm sales to any account over which it exercises discretionary authority without specific written approval of the account holder .See “Underwriting (Conflicts of Interest)—Conflicts of Interest.” |
| Risk Factors                       |     | You should consider all of the information contained in this prospectus supplement before making an investment in the notes. In particular, you should consider the risks described under “Risk Factors” in this prospectus supplement and in the filings we incorporate by reference herein.                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                     |

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### RISK FACTORS
An investment in the notes involves risks. You should consider carefully the following risk factors and all other information set forth and incorporated by reference in this prospectus supplement and accompanying prospectus, including the “Risk Factors” set forth in our most recent Annual Report on Form 20-F for information on factors that may affect our future results. These factors could cause our actual results to differ materially from those in the forward-looking statements contained in this prospectus supplement and other documents that we file with the SEC. These risks and uncertainties are not the only ones that we face or that relate to an investment in our notes. Additional risks not presently