Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 33

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 33
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 three series, which are the AHL PRD Shares, the AHL PRE Shares, which are represented by the AHL PRE Depositary Shares, and the AHL PRF Shares, which are represented by the AHL PRF Depositary Shares. For a more detailed description of our ordinary shares and Preference Shares, see “Description of Share Capital.”

The following diagram sets forth a simplified view of our corporate structure after giving effect to this offering and the Pre-IPO Transaction. The chart assumes no exercise of the option granted to the underwriters to purchase up to 1,987,500 additional ordinary shares in connection with the offering and an initial public offering price of $30.00 per ordinary share. This chart is for illustrative purposes only and does not represent all legal entities affiliated with the entities depicted. Unless otherwise noted, each entity is wholly-owned by its immediate parent.

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(1) Represents 48,041,181 ordinary shares held by AP Highlands Holdings and 29,364,539 ordinary shares held by AP Highlands Co-Invest. See “Principal and Selling Shareholders” for detail of the percentage ownership following this offering.

(2) Represents 1,182,646 ordinary shares held by certain members of our management team (including 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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#### Implications of Being a Foreign Private Issuer
We are considered a “foreign private issuer” and report under the Securities Exchange Act of 1934, as amended (the “Exchange Act”) as a non-U.S. company with foreign private issuer status. This means that, as long as we qualify as a foreign private issuer under the Exchange Act, we will be exempt from certain provisions of the Exchange Act that are applicable to U.S. domestic public companies, including:

• the sections of the Exchange Act regulating the solicitation of proxies, consents or authorizations in respect of a security registered under the Exchange Act;

• the sections of the Exchange Act requiring insiders to file public reports of their share ownership and trading activities and liability for insiders who profit from trades made in a short period of time; and

• the rules under