Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 0

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 0
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#### Filed Pursuant to Rule 424(b)(4)

#### Registration No. 333-276163
Prospectus

<div align='center'>13,250,000 Class A Ordinary Shares

Aspen Insurance Holdings Limited</div>

This is the initial public offering of the Class A ordinary shares, par value $0.001 per share, of Aspen Insurance Holdings Limited (the “ordinary shares”). The selling shareholders identified in this prospectus are offering 13,250,000 ordinary shares. We are not selling any ordinary shares under this prospectus and we will not receive any of the proceeds from the sale of ordinary shares by the selling shareholders.

Immediately prior to this offering, there has been no public market for our ordinary shares. The initial public offering price of our ordinary shares is $30.00 per ordinary share. Our ordinary shares have been approved for listing, subject to official notice of issuance, on the New York Stock Exchange (the “NYSE”) under the symbol “AHL.”

Following the completion of this offering, we will continue to have one class of authorized and issued ordinary shares and one class of authorized and issued preference shares, consisting of three series, which are our 5.625% Perpetual Non-Cumulative Preference Shares (“AHL PRD Shares”), our 5.625% Perpetual Non-Cumulative Preference Shares (“AHL PRE Shares”) and our 7.00% Perpetual Non-Cumulative Preference Shares (“AHL PRF Shares” and, together with our AHL PRD Shares and our AHL PRE Shares, the “Preference Shares”). The AHL PRE Shares are represented by depositary shares, each representing a 1/1000th interest in an AHL PRE Share (“AHL PRE Depositary Shares”). The AHL PRF Shares are represented by depositary shares, each representing a 1/1000th interest in an AHL PRF Share (“AHL PRF Depositary Shares” and, together with our AHL PRE Depositary Shares, the “Depositary Shares”). For a more detailed description of our ordinary shares and Preference Shares, see “Description of Share Capital.”

We are a “foreign private issuer” as defined under the U.S. federal securities laws and, as such, will be subject to reduced public company reporting and stock exchange governance requirements. See “Management and Corporate Governance—Foreign Private Issuer Exemption” for additional information.

AP Highlands Holdings, L.P., a Cayman exempted limited partnership (“AP Highlands Holdings”), and AP Highlands Co-Invest