Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 157

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 157
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### AUTHORIZED REPRESENTATIVE
Our authorized representative in the United States for this offering as required pursuant to Section 6(a) of the Securities Act is Cogency Global Inc., 22 East 42nd Street, 18th Floor New York, NY 10168.

<div align='center'>54</div>

### ASPEN INSURANCE HOLDINGS LIMITED
<div align='center'>$300,000,000</div>

#### 5.750% Senior Notes due 2030

### PROSPECTUS SUPPLEMENT

#### Joint Book-Running Managers
| Citigroup |     | Lloyds Securities |     | HSBC |

| BMO Capital Markets |     | Deutsche Bank Securities |     | nabSecurities, LLC |     | Natixis |     | Wells Fargo Securities |

#### Co-Managers
| Apollo Global Securities |     | Barclays |     | Goldman Sachs & Co. LLC |

#### June 10, 2025