Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 37

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 37
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 Company Status.”                                                                                                                                                                                                                    |

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(1) Includes the net issuance of 1,005,033 ordinary shares issued upon the completion of this offering as replacement awards with respect to legacy share option awards granted to certain employees of the Company as described in “Executive Compensation—2025 Equity and Incentive Plan” (after giving effect to the withholding of 301,106 ordinary shares to satisfy the estimated tax withholding and remittance obligations).

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| Risk factors          |     | See “Risk Factors” and the other information included in this prospectus for a discussion of factors you should consider before deciding to invest in our ordinary shares.                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                       |
| Conflicts of interest |     | Apollo Global Securities, LLC, an affiliate of Apollo, is an underwriter in this offering. Affiliates of Apollo beneficially own in excess of 10% of our issued and outstanding ordinary shares. In addition, the Apollo Shareholders are affiliates of Apollo and will receive in excess of 5% of the net proceeds of this offering. As a result, Apollo Global Securities, LLC is deemed to have a “conflict of interest” under Rule 5121 (“Rule 5121”) of the Financial Industry Regulatory Authority, Inc. (“FINRA”). Accordingly, this offering will be conducted in compliance with the requirements of Rule 5121. Pursuant to that rule, the appointment of a “qualified independent underwriter” is not required in connection with this offering as the members primarily responsible for managing the public offering do not have a conflict of interest, are not affiliates of any member that has a conflict of interest and meet the requirements of paragraph (f)(12)(E) of Rule 5121. See “Underwriting (Conflicts of Interest).” |

Except as otherwise noted, all information contained in this prospectus assumes: • the completion of the Pre-IPO Transaction; • no exercise of the option granted to the underwriters to purchase up to 1,987,500 additional ordinary shares from the selling shareholders in connection with the offering; • the net issuance of 1,005,033 ordinary shares issued upon the completion of this offering as replacement awards with respect to legacy share option awards granted to certain employees of the Company as described in “Executive Compensation—2025 Equity and Incentive Plan” (after giving effect to the withholding of 301,106 ordinary shares to satisfy the estimated tax withholding and remittance obligations); and • an initial public offering price of