Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 96

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 96
---
 collateral agent under the Private Facility) sell additional ordinary shares after this offering or are perceived by the public markets as intending to sell additional ordinary shares, the market price of our ordinary shares could decline.

The sale of substantial amounts of our ordinary shares in the public market, or the perception that such sales could occur, could harm the prevailing market price of our ordinary shares. These sales, or the possibility that these sales may occur, also might make it more difficult for us to sell ordinary shares in the future at a time and at a price that we deem appropriate.

AP Highlands Holdings and AP Highlands Co-Invest are each borrowers under the Private Facility. 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 term loan agreements (the “Term Loan Agreements”) with customary default provisions. Lenders and the collateral agent under the Private Facility will not be subject to a lock-up agreement in the event of a foreclosure on 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. Any foreclosure upon those ordinary shares by the lenders and/or the collateral agent could result in sales of a substantial number of our ordinary shares, which could substantially decrease the market price of our ordinary shares.

Upon completion of this offering, we will have a total of 91,838,366 ordinary shares outstanding. All of our ordinary shares sold in this offering will be freely tradable without restriction or further registration under the Securities Act, by persons other than our “affiliates,” as that term is defined under Rule 144 of the Securities Act. The remaining ordinary shares that will be outstanding after this offering are “restricted securities” within the meaning of Rule 144 under the Securities Act.

<div align='center'>64</div>

Prior to the completion of this offering, we intend to file one or more registration statements on Form S-8 under the Securities Act to register our ordinary shares to be issued under the 2025 Incentive Plan and the U.K. SIP. These registration statements will become effective immediately on filing. Shares covered by these registration statements will then be eligible for sale in public markets, subject to vesting restrictions, the lock