Company: AHL
Filing Date: 2025-06-09
Form Type: 424B5
Source: 0001628280-25-030114
Chunk: 17

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-06-09
Form: 424B5
Chunk 17
---
ness, 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 indebtedness. Accordingly, our ability to use the net proceeds from this offering for other purposes will be constrained.

U.S. persons who own our notes may have more difficulty in protecting their interests than U.S. persons who are creditors of a U.S. corporation.

Creditors of a company in Bermuda, such as Aspen Holdings, may enforce their rights against Aspen Holdings by legal process in Bermuda. The creditor would first have to obtain a judgment in its favor against Aspen Holdings by pursuing a legal action in Bermuda. This would entail retaining attorneys in Bermuda and (in the case of a plaintiff who is a U.S. person) pursuing an action in a jurisdiction which would be foreign to the plaintiff. The costs of pursuing such an action could be more costly than pursuing corresponding proceedings against a U.S. corporation.

Appeals from decisions of the Supreme Court of Bermuda (the first instance court for most civil proceedings in Bermuda) may be made in certain cases to the Court of Appeal for Bermuda. In turn, appeals from the decisions of the Court of Appeal may be made in certain cases to the Judicial Committee of the United