Company: AHL
Filing Date: 2025-06-11
Form Type: 424B5
Source: 0001628280-25-030754
Chunk: 17

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-11
Form: 424B5
Chunk 17
---
>

• entering into transactions with affiliates; and

• incurring liens.

Complying with these covenants could limit our financial and operational flexibility. We may also enter into future debt arrangements containing similar or different restrictive covenants. In addition, our failure to comply with these covenants could result in an event of default under our revolving credit facility, Term Loan Credit Agreement and other credit facilities. Such a default may allow the lenders thereunder to accelerate the loans and may result in the acceleration of any other debt which has a cross-acceleration or cross-default provision that applies to our revolving credit facility, Term Loan Credit Agreement and other credit facilities. In addition, an event of default under our revolving credit facility, Term Loan Credit Agreement and other credit facilities would permit the lenders to terminate all commitments to extend further credit under our revolving credit facility, Term Loan Credit Agreement and other credit facilities and demand early repayment. In the event our lenders or other debt holders accelerate the repayment of any borrowings that may be outstanding, we and our subsidiaries may not have sufficient assets or liquidity to repay that indebtedness, we may not be able to refinance such indebtedness on favorable terms, or at all, and these prepayment obligations could have an adverse effect on our results of operations and financial condition.

#### The notes may not constitute Tier 3 Capital.
We have applied for, and expect to receive from the BMA, formal approval which will permit the notes to qualify as Tier 3 Capital under the Insurance (Group Supervision) Rules 2011 (as amended) of Bermuda (the “Group Supervision Rules”) (subject to any applicable limitations on the amount of such capital). However, there is a risk that following any change to the Group Supervision Rules, the notes will cease to qualify as Tier 3 Capital of the Issuer. Under such circumstances, we may be required to raise additional capital that would constitute Tier 3 Capital or better capital treatment under the Group Supervision Rules at such time. Any such capital raise would be subject to market and other conditions, and there can be no assurance that we would be able to raise such capital when needed.

We are required to use the net proceeds from this offering to repay the indebtedness outstanding under the Term Loan Credit Agreement.

As of May 31, 2025, we had $300.0 million of indebtedness outstanding under the Term Loan Credit Agreement. Pursuant to the Term Loan Credit Agreement, we are required to use the net proceeds from this offering to repay such