Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 3

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 3
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together, “Aspen Lloyd’s”)), each referred to herein as an “Operating Subsidiary” and collectively referred to as the “Operating Subsidiaries.” References to “Aspen Capital Markets” or “ACM” means business conducted by our subsidiaries that participate in alternative reinsurance markets, including through Peregrine Reinsurance Ltd (“Peregrine”) and related management entities, including Aspen Capital Management, Ltd. (“ACML”). ACM forms part of the Aspen Capital Partners platform, in recognition of the synergies between ACM and the Company’s outwards reinsurance teams.

We manage our underwriting operations as two distinct business segments, insurance and reinsurance. References in this prospectus to our “Insurance segment” or “Aspen Insurance” refer to our Insurance segment and references to our “Reinsurance segment” or “Aspen Re” refer to our Reinsurance segment.

Under Bermuda law there is no concept of “outstanding” share capital. However, for purposes of this prospectus, to align with U.S. share capital terminology and for the avoidance of doubt, references to “outstanding” with respect to our share capital refer to our “issued” share capital under Bermuda law.

References in this prospectus to our “ordinary shares” refer to, prior to the Pre-IPO Transaction (as defined below), the ordinary shares, par value $0.01 per share, of Aspen. References in this prospectus to our “ordinary shares” or “Class A ordinary shares” refer to, subsequent to the Pre-IPO Transaction, the Class A ordinary shares, par value $0.001 per share, of Aspen. Upon the completion of the Exchange (as defined below), our issued and authorized ordinary shares, par value $0.01 per share, will cease to exist and our sole issued and outstanding class of ordinary shares will be the Class A ordinary shares, par value $0.001 per share. See “Summary—Our Corporate Structure and the Pre-IPO Transaction” for more information.

#### Exchange Control
Ordinary shares may be offered or sold in Bermuda only in compliance with the provisions of the Investment Business Act of 2003, as amended, the Bermuda Companies Act 1981, as amended (the “Companies Act”), and the Exchange Control Act 1972, as amended (the “Exchange Control Act”), and related regulations of Bermuda that

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regulate the sale of securities in Bermuda. In addition, specific permission is required from the