阿斯彭保险控股公司美股招股说明书(2025-06-11版)

Aspen Insurance Holdings Limited 5.750% Senior Notes due 2030 This is an offering by Aspen Insurance Holdings Limited (“Aspen Holdings” or the “Issuer”) of $300,000,000aggregate principal amount of5.750% SeniorNotes due 2030(the “notes”). The notes will bear interest at a rate of 5.750% per year. We will pay interest on the notes in arrears on January 1 and July 1of each year.The first interest payment on the notes will be due on January 1, 2026. The notes will mature on July 1, 2030. Under certain conditions, we will be required to deferrepayment of the notes on the Scheduled Maturity Date (as defined herein). See “Description of Notes—Maturity” and “Description of Notes—Conditions toRedemption and Repayment.” We intend to use the net proceeds from this offering, together with cash on hand, to repay the indebtedness outstanding under the TermLoan 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 subjectto 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 to100% 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 taxevents occur as described in “Description of Notes—Redemption for Tax Purposes.” Notwithstanding the foregoing, we may not repay or redeem the notes at any timeprior toJune 13, 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 atany time, including on the Scheduled Maturity Date, if the Enhanced Capital Requirement (as defined herein) would be breached immediately before or after givingeffect 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 capitalhaving 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 otherexisting and future obligations that are unsecured and unsubordinated, senior in right of payment to any future obligations we incur that are expressly subordinated inright 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 suchobligations and structurally and contractually subordinated to all existing and future obligations of our subsidiaries, including policyholder obligations. The notes willnot 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 pageS-7of this prospectussupplement and in our Annual Report on Form 20-F for the year ended December 31, 2024 incorporated herein by reference. Price to publicUnderwriting discountProceeds, before offering expenses, to us(1)(1) (1)Plus accrued interest, if any, from June 13, 2025. None of the Securities and Exchange Commission (the “SEC”), any state securities commission, the Bermuda Monetary Authority (the “BMA”) orany other regulatory body has approved or disapproved of these notes or passed upon the adequacy of this prospectus supplement. Any representation to thecontrary 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 itsparticipants, which may include Clearstream Banking S.A. (“Clearstream”) and Euroclear Bank SA/NV (“Euroclear”), against payment in New York, New York on orabout June 13, 2025. Joint Book-Running Managers HSBC Citigroup Deutsche BankSecurities Co-Managers Goldman Sachs & Co.LLC The date of this prospectus supplement is June 10, 2025. TABLE OF CONTENTS PROSPECTUS SUPPLEMENT ABOUT THIS PROSPECTUS SUPPLEMENTNOTE REGARDING FORWARD-LOOKING STATEMENTSSUMMARYRISK FACTORSUSE OF PROCEEDSCAPITALIZATION AND INDEBTEDNESSDESCRIPTION OF NOTESMATERIAL TAX CONSIDERATIONSUNDERWRITING (CONFLICTS OF INTEREST)VALIDITY OF THE SECURITIESEXPERTSWHERE YOU CAN FIND MORE INFORMATIONINCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE PROSPECTUS ABOUT THIS PROSPECTUSASPEN INSURANCE HOLDINGS LIMITEDRISK FACTORSCAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTSCAPITALIZATIONUSE OF PROCEEDSGENERAL DESCRIPTION OF THE OFFERED SECURITIESDESCRIPTION OF THE PREFERENCE SHARESDESCRIPTION OF THE DEPOSITARY SHARESDESCRIPTION OF THE DEBT SECURITIESCERTAIN PROVISIONS APPLICABLE TO THE SENIOR DEBT SECURITIESCERTAIN PROVISI