0000950136-05-007956 Sample Contracts

ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENT
Underwriting Agreement • December 13th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
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ASPEN INSURANCE HOLDINGS LIMITED UNDERWRITING AGREEMENT
Underwriting Agreement • December 13th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
ASPEN INSURANCE HOLDINGS LIMITED REMARKETING AGREEMENT
Remarketing Agreement • December 13th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York

Aspen Insurance Holdings Limited, a Bermuda company (the "Company"), is issuing and selling, on the date hereof, pursuant to the Underwriting Agreement, dated December 6, 2005 (the "Underwriting Agreement"), between the Company and Lehman Brothers Inc., as underwriter (the "Underwriter"), 4,000,000 of its 5.625% Perpetual Preferred Income Equity Replacement Securities (Perpetual PIERS) (the "Firm Securities"), $50 liquidation preference (the "Perpetual PIERS"). In addition, pursuant to the Underwriting Agreement, the Company has granted to the Underwriter an option to purchase up to an additional 600,000 Perpetual PIERS (the "Option Securities"; and, together with the Firm Securities, "the Offered Securities").

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