Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 98

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 98
---
 ordinary shares will be eligible for resale in the public market, subject, in the case of ordinary shares held by our affiliates, to volume, manner of sale and other limitations under Rule 144 and Rule 701. The market price of our ordinary shares may decline when the restrictions on resale lapse. A decline in the price of our ordinary shares might impede our ability to raise capital through the issuance of additional ordinary shares or other equity securities. For more information, see “Description of Share Capital” and “Shares Eligible for Future Sale.”

The Apollo Shareholders have engaged, and may continue to engage, in financing transactions whereby our ordinary shares are pledged as security.

In connection with the Private Facility, each of AP Highlands Holdings and AP Highlands Co-Invest has pledged all of our ordinary shares that it owns as collateral for borrowings under the Private Facility, excluding those shares being sold in this offering by each of AP Highlands Holdings and AP Highlands Co-Invest, pursuant to the Term Loan Agreements with customary default provisions. Additionally, the Apollo Shareholders may from time to time engage in additional financing transactions involving our ordinary shares whereby our ordinary shares are pledged as security. We are unable to influence the timing or terms of financing transactions (including the ability to pledge as collateral any of our ordinary shares they hold) by the Apollo Shareholders involving our ordinary shares.

In the event of a default under the Private Facility, the lenders and the collateral agent may foreclose upon any and all ordinary shares pledged to them and also may seek recourse against AP Highlands Holdings and/or AP Highlands Co-Invest. The foreclosure on our ordinary shares that are initially pledged as collateral under the Private Facility (or any similar future financing arrangement that may be entered into by the Apollo Shareholders) could, subject to obtaining required regulatory approvals (if applicable), cause a change of control of us that could trigger a default under, or acceleration of, the obligations under one or more of our financing arrangements, including, but not limited to, our 2026 Term Loan and our revolving credit facility. If such ordinary shares are sold, such sales could cause the trading price of our ordinary shares to decline. Sales of our ordinary shares in connection with the Private

<div align='center'>65</div>

Facility and any other such financing arrangement, whether by the Apollo Shareholders or upon enforcement against collateral, could have a material and adverse effect on our business, results of operations, access to equity capital and the trading price of our ordinary shares. In addition, the lenders might carry out hedging transactions