Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 20

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 20
---
 certain of the underwriters are lenders under the Term Loan Credit Agreement. As described above, because we intend to use the net proceeds from this offering, together with cash on hand, to repay the indebtedness outstanding under the Term Loan Credit Agreement, those affiliates will receive their proportionate share of the amount of such indebtedness that is repaid with the proceeds from this offering. Because at least 5% of the net proceeds from this offering will be used to repay the indebtedness outstanding under the Term Loan Credit Agreement owed to one or more individual underwriters and their affiliates, such underwriter has a “Conflict of Interest” within the meaning of FINRA Rule 5121, and this offering will be conducted in accordance with such rule. See “ Underwriting (Conflicts of Interest)—Conflicts of Interest .”

<div align='center'>S-12</div>

### CAPITALIZATION AND INDEBTEDNESS
The following table sets forth our cash and cash equivalents and consolidated capitalization as of March 31, 2025 on an actual basis and as adjusted to reflect this offering and the use of proceeds therefrom, as described under “Use of Proceeds.”

You should read this table in conjunction with “Management’s Discussion and Analysis of Financial Condition and Results of Operations” and Aspen Holdings’ consolidated financial statements and related notes that are included in Exhibit 99.1 to Aspen Holdings’ Report on Form 6-K filed with the SEC on June 3, 2025 and incorporated by reference into this prospectus supplement and the accompanying prospectus.

|                                                                                                                                                                                                                         |     | As of March 31, 2025                    |         |     |             |         |
|:------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|:----|:----------------------------------------|--------:|:----|:------------|--------:|
|                                                                                                                                                                                                                         |     | Actual                                  |         |     | As Adjusted |         |
|                                                                                                                                                                                                                         |     | -in millions, except for par value data |         |     |             |         |
| Cash and Cash Equivalents(1)                                                                                                                                                                                            |     | $                                       |   845.2 |     | $           |   841.6 |
| Long-term Debt Obligations(2):                                                                                                                                                                                          |     |                                         |         |     |             |         |
| Revolving Credit Facility(3)                                                                                                                                                                                            |     |                                         |       — |     |             |       — |
| 2026 Term Loan(1)                                                                                                                                                                                                       |     |                                         |