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

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 11
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| 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 known to us or that we currently deem immaterial may also impair our future business or results of operations. Any of these risks could result in a significant or material adverse effect on our results of operations or financial condition.

#### Risks Relating to the Notes
The notes will be contractually and structurally subordinated to all the indebtedness and other obligations of Aspen Holdings’ subsidiaries, and effectively subordinated to its secured indebtedness to the extent of the value of the assets securing such indebtedness, which may impact your ability to receive payment on the notes.

The rights of the holders of the notes to participate in any assets of any of our subsidiaries upon liquidation or reorganization of such subsidiaries will be structurally and contractually subordinated to the claims of such subsidiary’s policyholders and creditors.

The notes are obligations exclusively of us and will not be guaranteed by our subsidiaries. We are a holding company and conduct substantially all our operations through our subsidiaries. Our ability to meet our obligations under the notes will be dependent on the earnings and cash flows of our subsidiaries and the ability of our subsidiaries to pay dividends to us or to advance or repay funds to us, which are subject to regulatory and other restrictions. See “ Risk Factors—Risks Related to Our Preference Shares and Our Potential Initial Public Offering—Our holding company structure and certain Companies Act, regulatory and other constraints may limit our ability to pay dividends on our securities ” in our Annual Report on Form 20-F for the fiscal year ended December