Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 65

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 65
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 LAWS, AND OF ANY PROPOSED CHANGES IN APPLICABLE LAW.

<div align='center'>S-37</div>

#### UNDERWRITING (CONFLICTS OF INTEREST)
Subject to the terms and conditions of the underwriting agreement, the underwriters named below, through their representatives Citigroup Global Markets Inc., Lloyds Securities Inc. and HSBC Securities (USA) Inc., have severally, and not jointly, agreed to purchase from us the following respective principal amounts of notes listed opposite their names below at the public offering price less the underwriting discount set forth on the cover page of this prospectus supplement:

| Underwriters                    |     |   |     | Principal 
 Amount of 
 Notes     |             |            |
|:--------------------------------|:----|:--|:----|:----------|------------:|-----------:|
| Citigroup Global Markets Inc.   |     | $ |     |           |             | 60,000,000 |
| Lloyds Securities Inc.          |     |   |     |           |             | 60,000,000 |
| HSBC Securities (USA) Inc.      |     |   |     |           |             | 39,000,000 |
| BMO Capital Markets Corp.       |     |   |     |           |             | 21,000,000 |
| Deutsche Bank Securities Inc.   |     |   |     |           |             | 21,000,000 |
| nabSecurities, LLC              |     |   |     |           |             | 21,000,000 |
| Natixis Securities Americas LLC |     |   |     |           |             | 21,000,000 |
| Wells Fargo Securities, LLC     |     |   |     |           |             | 21,000,000 |
| Apollo Global Securities, LLC   |     |   |     |           |             | 12,000,000 |
| Barclays Capital Inc.           |     |   |     |           |             | 12,000,000 |
| Goldman Sachs & Co. LLC         |     |   |     |           |             | 12,000,000 |
| Total                           |     | $ |     |           | 300,000,000 |            |

The underwriting agreement provides that the obligations of the several underwriters to purchase the notes offered hereby are subject to certain conditions precedent and that the underwriters will purchase all of the