Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 503

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 503
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.0 |     | $          | -4.0 |     | $          | — |     | $          | — |     | $            | 21.0 |
| Reinsurance                                      |     | $               |    — |     | $          |    — |     | $          | — |     | $          | — |     | $            |    — |
| 2022                                             |     |                 |      |     |            |      |     |            |   |     |            |   |     |              |      |
| Premiums receivable from underwriting activities |     | $               | 30.2 |     | $          | -5.2 |     | $          | — |     | $          | — |     | $            | 25.0 |
| Reinsurance                                      |     | $               |    — |     | $          |    — |     | $          | — |     | $          | — |     | $            |    — |

<div align='center'>S-8

13,250,000 Ordinary Shares

Aspen Insurance Holdings Limited</div>

<div align='center'>Lead Book-Running Managers</div>

| Goldman Sachs & Co. LLC |     | Citigroup |     | Jefferies |

<div align='center'>Book-Running Managers</div>

| Apollo Global Securities |     | BMO Capital Markets |     | Deutsche Bank Securities |     | Morgan Stanley |     | RBC Capital Markets |     | Wells Fargo Securities |

| Citizens Capital Markets |     | Dowling & Partners Securities, LLC |     | Natixis |     | Piper Sandler |     | Raymond James |

<div align='center'>Co-Managers</div>

| Academy Securities |     | Siebert Williams Shank |

Through and including June 1, 2025 (the 25th day after the date of this prospectus), all dealers effecting transactions in these securities, whether or not participating in this offering, may be required to deliver a prospectus. This is in addition to the dealers’ obligation to deliver a prospectus when acting as an underwriter and with respect to an unsold allotment or subscription.