to a number of uncertainties and other factors, many of which are Appointment of Rights Agent 10 Section 3. further optimize the business portfolio, ensure capital efficiency and This press release contains written, and Aspen’s earnings conference www.aspen.co Investor Contact: Aspen Insurance Holdings Limited Ka99.2 - AHL Q1 15 Exhibit 99.2 FINANCIAL SUPPLEMENT As of March 31, 2015 Aspen Insurance Holdings Limited This financial supplement is for information purposes only. Company Inc. (“A.M. Aspen Insurance Holdings Limited. "We are excited about the next chapter in our history with a partner WHEREAS, the Executive and the Company wish to enter into a written agreement setting forth the terms and conditions of the Executive’s employment with tEX-99. Reform Act of 1995. It should be read in conjunction with other documents filed or to be filed by Aspen Insurance Holdings Limited with the United States Securities and Exchange Commission. Aspen’s BoardEX-99. www.aspen.co Investor Contact: Aspen Insurance Holdings Limited Mark Jones, SeExhibit 99.1 PRESS RELEASE ASPEN REPORTS RESULTS FOR QUARTER ENDED SEPTEMBER 30, 2018 Annualized Operating Return on Equity of 5.2% for the Third Quarter 2018 and 7.6% for First Nine Months 2018 Annualized Net Income Return on Equity of (4.0)% for the Third Quarter 2018 and (1.2)% for First Nine Months 2018 Hamilton, Bermuda, October 24, 2018 - Aspen Insurance Holdings Limited (“Aspen”) (NYSE: AHLOctober 1, 2018 Dear Colleague, After more than 16 supremely enjoyable years leading Aspen I will step down from the position of CEO on or shortly after the completion of our acquisition by investment funds managed by affiliates of Apollo Global Management, LLC.EX-99.1 Exhibit 99.1 PRESS RELEASE Aspen Insurance Holdings Limited Enters into a Definitive Agreement to be Acquired by Certain Investment Funds Affiliated with Apollo Global Management in an All-Cash Transaction Valued at $2.6 Billion New York and Hamilton, Bermuda, August 28, 2018 – Affiliates of certain investment funds (the “Apollo Funds”) managed by affiliates of Apollo Global Management, LLEX-99.7 Exhibit 99.7 Talking Points for Discussions with Clients and Broker Partners • Aspen has announced that it has entered into an agreement to be acquired by affiliates of certain investment funds managed by affiliates of Apollo Global Management, LLC. income.

It should be read in conjunction with other documents filed or to be filed by Aspen Insurance Holdings Limited with the United States Securities and Exchange Commission. LEGAL FEES 7 9. For For the purpose of these proposals, the references to the Group mean the Company, its subsidiaries and subsidiary undertakings and any holding company or pareExhibit 10.1 MENDED AND RESTATED ACCOUNT CONTROL AGREEMENT AMENDED AND RESTATED PLEDGE AGREEMENT AMENDED AND RESTATED PLEDGE AGREEMENT, dated as of December 18, 2014 (as may be amended, restated or otherwise modified from time to time, this “Agreement”), made among ASPEN BERMUDA LIMITED, a company organized and existing under the laws of Bermuda whose address of its registered or principal office Exhibit 10.1 FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT THIS FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”) dated as of December 12, 2014 is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that are parties hereto, and BarclayAMENDMENT AGREEMENT (“Amendment”) dated as of October 28, 2014 between Charles Christopher O’Kane and Aspen Insurance UK Services Limited (“AIUKSL”) Aspen Insurance Holdings Limited (“AIHL” and, together with Mr.JamesFew-SeveranceAgreementFinal (1) DATED OCTOBER 20, 2014 ASPEN BERMUDA LIMITED (1) and JAMES RICHARD FEW (2) _ SEVERANCE AGREEMENT _ Willkie Farr & Gallagher (UK) LLP City Point 1 Ropemaker Street London EC2Y 9AW Tel: +44 (0)20 3580 4700 Fax: +44 (0)20 3580 4800 www.willkie.com THIS AGREEMENT is made as of the 20th day of October 2014 BETWEEN: (1) ASPEN BERMUDA LIMIT1 North Wall Quay Dublin 1 Ireland T +353 1 622 2000 F +353 1 622 2222 Niall Tuckey Director ILOC Product Citibank Europe plc 1 North Wall Quay Dublin 1, Ireland Tel+353 (1) 622 7430 Fax+353 (1) 622 2741 Niall.1 North Wall Quay Dublin 1 Ireland T +353 1 622 2000 F +353 1 622 2222 Niall Tuckey Director ILOC Product Citibank Europe plc 1 North Wall Quay Dublin 1, Ireland Tel+353 (1) 622 7430 Fax+353 (1) 622 2741 Niall.EX-10.2 Exhibit 10.2 EXECUTION FIRST AMENDMENT First Amendment, dated as of June 25, 2014 (this “Amendment”), to the Credit Agreement (as defined below) and the Security Agreement (as defined below), by and among Endurance Specialty Holdings Ltd., a company organized under the laws of Bermuda (the “Parent Borrower”), each Designated Subsidiary Borrower (as defined in the Credit Agreement (as definEX-10.1 Exhibit 10.1 EXECUTION VERSION Morgan Stanley Senior Funding, Inc. 1585 Broadway New York, NY 10036 Endurance Specialty Holdings Ltd. Wellesley House 90 Pitts Bay Road Pembroke, HM 08 Bermuda June 25, 2014 PROJECT SAIL $1,000,000,000 Senior Unsecured 364-Day Bridge Facility Joinder Agreement to Commitment Letter Ladies and Gentlemen: Reference is made to the Commitment Letter regarding a $EX-10.1 Exhibit 10.1 EXECUTION VERSION PRIVILEGED AND CONFIDENTIAL Morgan Stanley Senior Funding, Inc. 1585 Broadway New York, New York 10036 June 2, 2014 Endurance Specialty Holdings Ltd. Wellesley House 90 Pitts Bay Road Pembroke, HM 08 Bermuda Attention: Michael J. McGuire, Chief Financial Officer Ladies and Gentlemen: Project Sail $1,000,000,000 Facility Commitment Letter You (“you” or the “BoEX-10.2 Exhibit 10.2 EXECUTION COPY AGREEMENT This AGREEMENT (this “Agreement”), dated as of June 2, 2014, is made and entered into by and among CVC Capital Partners Advisory (U.S.), Inc. (“CVC”), GIC Special Investments Pte.