Company: AHL
Filing Date: 2025-04-29
Form Type: F-1/A
Source: 0001628280-25-020463
Chunk: 40

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-04-29
Form: F-1/A
Chunk 40
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 of 1,011,414 ordinary shares after giving effect to the withholding of 303,013 ordinary shares to satisfy the estimated tax withholding and remittance obligations; and a $1.00 decrease in the assumed initial public offering price of $30.00 per ordinary share, the midpoint of the price range set forth on the cover page of this prospectus, would decrease the number of ordinary shares issued as replacement awards to an aggregate net issuance of 1,004,663 ordinary shares after giving effect to the withholding of 300,992 ordinary shares to satisfy the estimated tax withholding and remittance obligations); and • an initial public offering price of $30.00 per ordinary share, which is the midpoint of the price range set forth on the cover page of this prospectus. The number of ordinary shares that will be outstanding after this offering is based on 91,841,482 ordinary shares outstanding after giving effect to the Pre-IPO Transaction and the net issuance of 1,008,149 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” (based on an assumed initial public offering price of $30.00 per ordinary share, which is the midpoint of the price range set forth on the cover page of this prospectus, and after giving effect to the withholding of 302,038

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ordinary shares to satisfy the estimated tax withholding and remittance obligations). The number of ordinary shares that will be outstanding after this offering excludes:

• 3,633,333 ordinary shares reserved for future issuance under the Aspen Insurance Holdings Limited 2025 Equity and Incentive Plan (the “2025 Incentive Plan”) as described in “Executive Compensation—2025 Equity and Incentive Plan” of which: (i) 792,695 ordinary shares will be issuable upon the vesting of restricted share units granted in connection with this offering under the 2025 Incentive Plan (as described in the third bullet of this paragraph); and (ii) 577,768 ordinary shares may be issued upon the exercise of share options granted in connection with this offering under the 2025 Incentive Plan (as described in the fourth bullet of this paragraph);

• 227,083 ordinary shares reserved for future issuance under a tax-advantaged Share Incentive Plan (the “U.K. SIP”) as described in “