Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 393

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 393
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 of Bermuda (together, the “Payroll Tax Act”), an employer is required to pay payroll tax on remuneration paid to each employee, up to a maximum of $1 million (no tax liability accrues on sums above $1 million). Liability for payroll tax is calculated by reference to services provided wholly or mainly in Bermuda during four tax periods, being periods of three months commencing on the first day of April, July, October and January. The meaning of “employee” under the Payroll Tax Act includes deemed employees and covers a broad range of employment structures. Subject to certain express exclusions, “remuneration” is also very broadly defined, to capture any benefit of any kind paid to employees or deemed employees, whether in cash or otherwise. This includes, for example, any gain obtained by the exercise, assignment or release of any option awarded under any option plans. Payroll tax is levied on employers and employees separately, with different marginal rates; however, employers are liable to pay the full amount of payroll tax and are permitted to deduct and remit to the Bermuda Tax Commissioner the amount of the employee’s liability from their remuneration.

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#### UNDERWRITING (CONFLICTS OF INTEREST)
We, the selling shareholders and the underwriters named below have entered into an underwriting agreement with respect to the ordinary shares being offered. Subject to certain conditions, each underwriter has severally agreed to purchase the number of ordinary shares indicated in the following table. Goldman Sachs & Co. LLC, Citigroup Global Markets Inc. and Jefferies LLC are the representatives of the underwriters.

| Underwriters                       |     | Number of Ordinary Shares |     |            |
| Goldman Sachs & Co. LLC            |     |                           |     |  3,243,285 |
| Citigroup Global Markets Inc.      |     |                           |     |  2,573,475 |
| Jefferies LLC                      |     |                           |     |  2,220,944 |
| Apollo Global Securities, LLC      |     |                           |     |  1,410,123 |
| BMO Capital Markets Corp.          |     |                           |     |    460,870 |
| Deutsche Bank Securities Inc.      |     |                           |     |    460,870 |
| Morgan Stanley & Co. LLC           |     |                           |     |    460,870 |
| RBC Capital Markets, LLC           |