0000950123-10-112677 Sample Contracts

ASPEN INSURANCE HOLDINGS LIMITED $250,000,000 6.00% Senior Notes due 2020 UNDERWRITING AGREEMENT
Underwriting Agreement • December 10th, 2010 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

CITIGROUP GLOBAL MARKETS INC. DEUTSCHE BANK SECURITIES INC. As Representatives of the several Underwriters named in Schedule 1

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SECOND SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER AND DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE
Second Supplemental Indenture • December 10th, 2010 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

This Second Supplemental Indenture, dated as of December 10, 2010 (the “Second Supplemental Indenture”), to the Indenture, dated as of August 16, 2004 (the “Original Indenture”) by and between Aspen Insurance Holdings Limited, a limited company duly organized and existing under the laws of Bermuda, having its principal executive office located at Maxwell Roberts Building, 1 Church Street, Hamilton HM 11, Bermuda (the “Company”), as issuer, and Deutsche Bank Trust Company Americas, a New York banking corporation duly organized and existing under the laws of the State of New York, having its corporate trust office located at 60 Wall Street, New York, NY 10005 (the “Trustee”), as trustee, is effective upon the execution hereof by the parties hereto.

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