Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 12

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 12
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 the extent of the value of the assets securing that indebtedness. As of May 31, 2025, without giving effect to the offering of the notes and the application of the proceeds therefrom, we had $300.0 million principal amount of outstanding senior indebtedness, none of which would have been secured indebtedness.

If a public market for the notes does not develop, your ability to resell the notes and the market price for the notes may be adversely affected.

The notes are a new issue for which there is no established trading market. The notes will not be listed on any securities exchange or automated quotation system. Although the underwriters have advised us that they intend to make a market in the notes, they are not obligated to do so and could stop making a market in the notes at any time without notice. The liquidity of any market for the notes will depend on the number of holders of the notes, the interest of securities dealers in making a market in the notes and other factors. A trading market for the notes may not develop or any such market may not have sufficient liquidity. The price at which you will be able to sell the notes may be less than the price paid for them due to prevailing interest rates, the market for similar securities, general economic conditions, our performance and business prospects and other factors.

We may not have the ability to raise the funds necessary to pay the principal of or interest on the notes.

Upon maturity, the entire principal amount of the notes then outstanding, plus any accrued and unpaid interest, will become due and payable. We must pay interest in cash on the notes on and of each year, beginning on , 2025. We may not have enough available cash or be able to obtain sufficient financing, on favorable terms or at all, at the time we are required to make these payments. Furthermore, our ability to make these

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payments may be limited by law, by regulatory authority or by agreements governing our existing or future indebtedness. Our failure to pay interest when due, if uncured for 30 days, or our failure to pay the principal amount when due, in each case other than if we are required to defer payment due to failure to satisfy the BMA Redemption Requirements (as defined in “ Description of Notes—Conditions to Redemption and Repayment ”), will constitute an event of default under the indenture governing the notes. A default under the indenture could also lead to a default under agreements governing our existing or future indebtedness. If