Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 1

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 1
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, L.P., a Cayman exempted limited partnership (“AP Highlands Co-Invest” and, together with AP Highlands Holdings, the “Apollo Shareholders”), each an affiliate of certain investment funds managed by affiliates of Apollo Global Management, Inc. (collectively with its subsidiaries, “Apollo”), are the selling shareholders in this offering (the “selling shareholders”). Following this offering, the Apollo Shareholders will collectively beneficially own approximately 84.3% of our ordinary shares (or 82.1% if the underwriters exercise in full their option to purchase additional ordinary shares from the selling shareholders). As a result, we will be a “controlled company” under the corporate governance rules of the NYSE applicable to listed companies, and therefore are permitted to elect not to comply with certain corporate governance requirements thereunder.

Investing in our ordinary shares involves a high degree of risk. Before investing in our ordinary shares, you should carefully read the “

#### Risk Factors

#### ” beginning on page

#### 32

#### of this prospectus.
Neither the Securities and Exchange Commission (the “SEC”) nor any other regulatory body has approved or disapproved of these securities or passed upon the accuracy or adequacy of this prospectus. Any representation to the contrary is a criminal offense.

|                                                        |     | Per ordinary share |         |     | Total |             |
|:-------------------------------------------------------|:----|:-------------------|--------:|:----|:------|------------:|
| Initial public offering price                          |     | $                  | 30.0000 |     | $     | 397,500,000 |
| Underwriting discount(1)                               |     | $                  |  1.7250 |     | $     |  22,856,250 |
| Proceeds, before expenses, to the selling shareholders |     | $                  | 28.2750 |     | $     | 374,643,750 |

__________________

(1) Please see “Underwriting (Conflicts of Interest)” for a description of all compensation payable to the underwriters.

The underwriters have an option to purchase up to an additional 1,987,500 ordinary shares from the selling shareholders at the initial public offering price less the underwriting discount for 30 days from the date of this prospectus.

The underwriters expect to deliver the ordinary shares against payment in New York, New York on or about May 9, 2025.

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