Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 332

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 332
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 Securities Act or if they qualify for an exemption from registration, including an exemption under Rule 144 or Rule 701, which are summarized below.

Of the 91,838,366 of our ordinary shares outstanding immediately following this offering, 78,588,366 ordinary shares (or 76,600,866 ordinary shares if the underwriters exercise their option to purchase additional ordinary shares from the selling shareholders in full) are restricted securities, as that term is defined in Rule 144 under the Securities Act, or are subject to lock-up agreements as described herein.

As defined in Rule 144, an “affiliate” of an issuer is a person that directly, or indirectly through one or more intermediaries, controls, is controlled by or is under common control with the issuer.

#### Form S-8 Registration Statements
Prior to the completion of this offering, we intend to file one or more registration statements on Form S-8 under the Securities Act to register our ordinary shares to be issued under the 2025 Incentive Plan and the U.K. SIP. These registration statements will become effective immediately on filing. Shares covered by these registration statements will then be eligible for sale in public markets, subject to vesting restrictions, the lock-up agreements described below (if applicable) and Rule 144 limitations applicable to affiliates.

#### Lock-up Agreement
We and our executive officers, directors and the Apollo Shareholders will agree with the underwriters, subject to certain exceptions, not to dispose of or hedge any of our ordinary shares or securities convertible into or exchangeable for our ordinary shares during the period from the date of this prospectus continuing through the date 180 days after the date of this prospectus, except with the prior written consent of any two of the representatives of the underwriters. These lock-up agreements contain important exceptions that govern their applicability, including, with respect to the Apollo Shareholders, (1) the pledge or related transfer of our ordinary shares as collateral or security pursuant to the Private Facility, including in connection with any foreclosure and transfer in connection therewith, (2) pledging, hypothecating, granting or making any related transfer of our ordinary shares to any third-party pledgee in a bona fide transaction as collateral to secure obligations pursuant to lending or other arrangements between such third parties (or their affiliates or designees) and the lock-up party and/or its affiliates or any similar

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arrangement relating to a financing arrangement for the benefit of the lock-up party and/or its affiliates