Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 0

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 0
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#### Filed Pursuant to Rule 424(b)(5)

#### Registration No. 333-272650
The information in this preliminary prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell these securities and we are not soliciting offers to buy these securities in any jurisdiction where the offer or sale is not permitted.

#### SUBJECT TO COMPLETION, DATED JUNE 9, 2025

#### Preliminary Prospectus Supplement
(To Prospectus dated June 26, 2023)

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#### Aspen Insurance Holdings Limited

#### % Senior Notes due 20
This is an offering by Aspen Insurance Holdings Limited (“Aspen Holdings” or the “Issuer”) of $ aggregate principal amount of % Senior Notes due 20 (the “notes”). The notes will bear interest at a rate of % per year. We will pay interest on the notes in arrears on and of each year. The first interest payment on the notes will be due on , 2025. The notes will mature on , 20 . Under certain conditions, we will be required to defer repayment of the notes on the Scheduled Maturity Date (as defined herein). See “ Description of Notes—Maturity ” and “ Description of Notes—Conditions to Redemption and Repayment .” 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 (as defined herein). See “ Use of Proceeds .”

The notes will be redeemable prior to maturity, in whole at any time or in part from time to time, at our option, at the applicable redemption price and subject to the terms described in “ Description of Notes—Optional Redemption .” Additionally, we may redeem the notes, in whole but not in part, at a redemption price equal to 100% of the principal amount, together with accrued and unpaid interest and additional amounts, if any, to, but excluding, the redemption date at any time certain tax events occur as described in “ Description of Notes—Redemption for Tax Purposes .” Notwithstanding the foregoing, we may not repay or redeem the notes at any time prior to , 2028 (three years after the initial issue date of the notes) without BMA Approval (as defined herein). Further, we may not repay or redeem the notes at any time, including on the Scheduled Maturity Date, if the Enhanced Capital Requirement (