Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 1

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 1
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as defined herein) would be breached immediately before or after giving effect to the redemption or repayment of such notes, unless we or a subsidiary of ours replaces the capital represented by the notes to be redeemed or repaid with capital having equal or better capital treatment as the notes under the Group Rules (as defined herein).

Subject to applicable law, the notes will be our unsecured and unsubordinated obligations and will rank equally in right of payment with all of our other existing and future obligations that are unsecured and unsubordinated, senior in right of payment to any future obligations we incur that are expressly subordinated in right of payment to the notes, effectively subordinated to any of our existing and future secured obligations to the extent of the value of the assets securing such obligations and structurally and contractually subordinated to all existing and future obligations of our subsidiaries, including policyholder obligations. The notes will not be guaranteed by any of our subsidiaries.

The notes will not be listed on any securities exchange or automated quotation system. Currently, there is no public market for the notes.

Investing in the notes involves risks. You should carefully consider the information under “

#### Risk Factors

#### ” beginning on page

#### S- 7
of this prospectus supplement and in our Annual Report on Form 20-F for the year ended December 31, 2024 incorporated herein by reference.

|                                              |     | Per Note |     | Total |     |   |
|:---------------------------------------------|:----|:---------|:----|:------|:----|:--|
| Price to public(1)                           |     | %        |     | $     |     |   |
| Underwriting discount                        |     | %        |     |       |     | $ |
| Proceeds, before offering expenses, to us(1) |     | %        |     |       |     | $ |

__________________

(1) Plus accrued interest, if any, from , 2025.

None of the Securities and Exchange Commission (the “SEC”), any state securities commission, the Bermuda Monetary Authority (the “BMA”) or any other regulatory body has approved or disapproved of these notes or passed upon the adequacy of this prospectus supplement. Any representation to the contrary is a criminal offense.

We expect that delivery of the notes will be made through the book-entry facilities of The Depository Trust Company (“DTC”) for the accounts of its participants, which may include Clearstream Banking S.A. (“Clearstream”) and Euroclear