Company: AHL
Filing Date: 2025-05-08
Form Type: 424B4
Source: 0001628280-25-023859
Chunk: 290

Company: ASPEN INSURANCE HOLDINGS LTD
Filing Date: 2025-05-08
Form: 424B4
Chunk 290
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 economic rights as our existing ordinary shares other than par value. Following the Exchange, Highlands Bermuda Holdco, Ltd. will, pursuant to its plan of liquidation, distribute all 90,833,333 Class A ordinary shares that it received in the Exchange to AP Highlands Holdings, AP Highlands Co-Invest and certain members of our management team. As a result of the Pre-IPO Transaction, all of our issued and outstanding Class A ordinary shares previously held by Highlands Bermuda Holdco, Ltd. will, after the Pre-IPO Transaction, be held by the existing holders of equity interests in Highlands Bermuda Holdco, Ltd., including AP Highlands Holdings and AP Highlands Co-Invest, both of which are affiliated with and managed by affiliates of Apollo, and certain members of our management team, and our sole issued and outstanding class of ordinary shares will be our Class A ordinary shares. Upon completion of the Pre-IPO Transaction, but prior to the consummation of this offering and the sale of our Class A ordinary shares by the selling shareholders, we will have 90,833,333 Class A ordinary shares issued and

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outstanding, 56,264,677 Class A ordinary shares of which will be held by AP Highlands Holdings, 34,391,043 Class A ordinary shares of which will be held by AP Highlands Co-Invest and 177,613 Class A ordinary shares of which will be held by certain members of our management team.

#### Information Technology Outsourcing Agreement
In August 2018, Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services Inc. and Aspen Bermuda entered into an Outsourcing Agreement (the “Original IT Outsourcing Agreement”) with Cognizant Worldwide Limited, a company registered in England (“Cognizant”). Pursuant to the Original IT Outsourcing Agreement, Cognizant provided the Company with information technology services to enable us to deliver greater operating effectiveness and efficiencies. The Original IT Outsourcing Agreement became effective in August 2018 and had an initial term period of five years beginning in October 2018. The Company had the right to extend the Original IT Outsourcing Agreement for an additional two-year term.

In December 2020, Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services Inc. and Aspen Bermuda entered into a new Outsourcing Agreement (the “IT Outsourcing Agreement”) with Cognizant, which replaced and superseded the Original IT Outsourcing Agreement and significantly reduced the information technology services provided thereunder. The IT