Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 11

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 11
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 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 31, 2024. Our right to participate as an equity holder in any distribution of assets of any subsidiary (and thus the ability of holders of the notes to benefit as creditors of Aspen Holdings from such distribution) is junior to creditors of that subsidiary, including policyholders, trade creditors, debt holders, taxing authorities, guarantee holders and preference shareholders. As a result, claims of holders of the notes will be structurally subordinated to the claims of existing and future policyholders and other creditors of our subsidiaries. In the event of our liquidation or reorganization, holders of the notes will generally have a junior position to claims of creditors of our subsidiaries. As of March 31, 2025, the liabilities of our subsidiaries that were structurally senior to the notes were $9,648.9 million. Our subsidiaries may incur additional debt and liabilities in the future, all of which would rank structurally senior to the notes.

The notes will not be secured, and thus the notes will be effectively subordinated to our existing and future secured indebtedness to