UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, DC 20549

FORM 8-K

Current Report
Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): November 10, 2006

ASPEN INSURANCE HOLDINGS LIMITED
(Exact name of registrant as specified in its charter)


Bermuda 001-31909 Not Applicable
(State or other jurisdiction
of incorporation)
(Commission
File Number)
(I.R.S. Employer
Identification No.)

Maxwell Roberts Building
1 Church Street
Hamilton HM 11
Bermuda
(Address of principal executive offices)
(Zip Code)

Registrant’s telephone number, including area code: ( 441) 295-8201

Not Applicable
(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

[    ]  Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
[    ]  Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
[    ]  Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
[    ]  Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))



Item 3.03     Material Modification to Rights of Security Holders

Preference Share Offering

On November 10, 2006, Aspen Insurance Holdings Limited, a Bermudian company (the ‘‘Company’’) entered into an underwriting agreement relating to 8,000,000 7.401% Perpetual Non-Cumulative Preference Shares, par value 0.15144558¢ each, and liquidation preference of $25 per share (the ‘‘Preference Shares’’) with Lehman Brothers Inc. and UBS Securities LLC, as representatives of the several underwriters named in Schedule 1 thereto (the ‘‘Underwriting Agreement’’), pursuant to which the underwriters agreed to purchase the Preference Shares from the Company. A copy of the Underwriting Agreement is attached as Exhibit 1.1 hereto.

The Preference Shares are being offered and sold pursuant to the shelf registration statement on Form F-3 (File No. 333-129214), dated November 2, 2005 (the ‘‘Registration Statement’’) filed by the Company with the Securities Exchange Commission (the ‘‘Commission’’) under the Securities Act of 1933, as amended (the ‘‘Securities Act’’), and the related prospectus supplement, dated November 10, 2006 (the ‘‘Preference Shares Prospectus Supplement’’), with respect to the Preference Shares. The terms of the Preference Shares are set forth in the Preference Shares Prospectus Supplement, as filed with the Commission pursuant to Rule 424(b) under the Securities Act on November 14, 2006.

On November 15, 2006, in connection with the transactions described above, the Company authorized and issued a certificate of designations (the ‘‘Certificate of Designations’’) setting forth the terms of the Preference Shares. A copy of the form of the Certificate of Designations is attached as Exhibit 4.1 hereto.

Replacement Capital Covenant

On November 15, 2006, in connection with the transactions described above, the Company entered into a Replacement Capital Covenant (the ‘‘Replacement Capital Covenant’’) with respect to the Preference Shares initially for the benefit of persons that hold the Company's 6.00% senior notes due August 15, 2014 (the ‘‘Senior Notes’’), that the Company will not redeem or repurchase the Preference Shares on or before November 15, 2046, unless, during the six months prior to the date of that redemption or repurchase, the Company receives a specified amount of proceeds from the sale of ordinary shares, preference shares and certain other securities that have characteristics that are the same as, or more equity-like than, the applicable characteristics of the Preference Shares at the time of that redemption or repurchase.

In order to give effect to the intent of the Company set forth in Recital C of the Replacement Capital Covenant, the Company is entering into and disclosing the content of the Replacement Capital Covenant with the intent that the covenants provided for in the Replacement Capital Covenant be enforceable by each Covered Debtholder (as defined in the Replacement Capital Covenant), and that the Company be estopped from disregarding its covenants in the Replacement Capital Covenant. Initially, the holders of the Senior Notes will be the Covered Debtholders, although such designation may change without the consent of the holders of the Senior Notes. The Replacement Capital Covenant may terminate in the event that the Company no longer has any outstanding debt that is considered Covered Debt (as defined in the Replacement Capital Covenant) or the Company no longer has any Preference Shares outstanding, and will terminate on November 15, 2046, unless earlier terminated. A copy of the form of the Replacement Capital Covenant is attached as Exhibit 4.3 hereto.

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Item 9.01 Financial Statements and Exhibit
(d) Exhibits
  The following exhibits are filed as part of this report:
1.1  Underwriting Agreement, dated November 10, 2006 among the Company and Lehman Brothers Inc. and UBS Securities LLC, as representative of the several underwriters names in Schedule 1 thereto.
4.1 Form of Certificate of Designations of the Company's Preference Shares, dated November 15, 2006.
4.2  Specimen Certificate for the Company's Preference Shares, dated November 15, 2006 (the form of which is incorporated in Exhibit 4.1).
4.3 Form of Replacement Capital Covenant, dated November 15, 2006.

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SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.


  ASPEN INSURANCE HOLDINGS LIMITED
  (Registrant)
Dated: November 15, 2006 By: /s/ Julian Cusack
  Name:    Julian Cusack
  Title:      Chief Financial Officer



Exhibit 1.1

8,000,000 Shares

ASPEN INSURANCE HOLDINGS LIMITED

7.401% Perpetual Non-Cumulative Preference Shares
(Liquidation Preference $25 Per Share)

UNDERWRITING AGREEMENT

November 10, 2006

LEHMAN BROTHERS INC .
745 Seventh Avenue
New York, NY 10019

UBS SECURITIES LLC
677 Washington Boulevard
Stamford, CT 06901

As Representatives of the several
    Underwriters named in Schedule 1,

Dear Sirs:

1.         Introductory.     Aspen Insurance Holdings Limited, a Bermuda company (the ‘‘ Company ’’), proposes to issue and sell to the several underwriters named in Schedule 1 hereto (the ‘‘ Underwriters ’’), for whom you (the ‘‘ Representatives ’’) are acting as representatives, an aggregate of 8,000,000 of its 7.401% Perpetual Non-Cumulative Preference Shares (the ‘‘ Securities ’’), with a liquidation preference of $25 per share (the ‘‘ Preference Shares ’’), which shall have the rights, powers and preferences set forth in the Certificate of Designation of Perpetual Non-Cumulative Preference Shares (the ‘‘ Certificate of Designation ’’). The ordinary shares, par value $.0015144558 per share, of the Company, are hereinafter referred to as the ‘‘ Ordinary Shares ’’.

The Company hereby agrees with the several Underwriters as follows:

2.         Representations, Warranties and Agreements of the Company.     The Company represents and warrants to, and agrees with, each Underwriter that:

(i)    A registration statement (No. 333-129214) relating to the Securities has been prepared by the Company, including a prospectus (the ‘‘ initial registration statement ’’) has been filed with the Securities and Exchange Commission (the ‘‘ Commission ’’) and has been declared effective under the Securities Act of 1933, as amended (the ‘‘ Act ’’) and either (A) is not proposed to be amended or (B) is proposed to be amended by amendment or post-effective amendment. Either (A) an additional registration statement (the ‘‘ additional registration statement ’’) relating to the Securities may have been filed with the Commission pursuant to Rule 462(b) (‘‘ Rule 462(b) ’’) under the Act (if available) and, if so filed, has become effective upon filing pursuant to such Rule and the Securities have been duly registered under the Act pursuant to the initial registration statement and, if applicable, the additional registration statement or (B) such an additional registration statement is proposed to be filed with the Commission pursuant to Rule 462(b) (if available) and will become effective upon filing pursuant to such Rule, and upon such filing the Securities will all have been duly registered under the Act pursuant to the initial registration statement and such additional registration statement. If the Company does not propose to amend the initial registration statement or if an additional registration statement has been filed and the Company does not propose to amend it, and if any post-effective amendment to either such registration statement has been filed with the Commission prior to the execution and delivery of this Agreement, the most recent amendment (if any) to each such registration statement has been declared effective by the Commission or has become effective upon

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filing pursuant to Rule 462(c) (‘‘ Rule 462(c) ’’) under the Act or, in the case of the additional registration statement, Rule 462(b). For purposes of this Agreement, ‘‘ Effective Time ’’ with respect to the initial registration statement or, if filed prior to the execution and delivery of this Agreement, the additional registration statement means (A) if the Company has advised the Representatives that it does not propose to amend such registration statement, the date and time as of which such registration statement, or the most recent post-effective amendment thereto (if any) filed prior to the execution and delivery of this Agreement, was declared effective by the Commission or has become effective upon filing pursuant to Rule 462(c), or (B) if the Company has advised the Representatives that it proposes to file an amendment or post-effective amendment to such registration statement, the date and time as of which such registration statement, as amended by such amendment or post-effective amendment, as the case may be, is declared effective by the Commission. If an additional registration statement has not been filed prior to the execution and delivery of this Agreement but the Company has advised the Representatives that it proposes to file one, ‘‘ Effective Time ’’ with respect to such additional registration statement means the date and time as of which such registration statement is filed and becomes effective pursuant to Rule 462(b). ‘‘ Effective Date ’’ with respect to the initial registration statement or the additional registration statement (if any) means the date of the Effective Time thereof. The initial registration statement, as amended at its Effective Time, including all material incorporated by reference therein and including all information contained in the additional registration statement (if any) and deemed to be a part of the initial registration statement as of the Effective Time of the additional registration statement (if any) pursuant to the General Instructions of the Form on which it is filed, is hereinafter referred to as the ‘‘ Initial Registration Statement ’’. The additional registration statement (if any), as amended at its Effective Time, including the contents of the initial registration statement incorporated by reference therein, is hereinafter referred to as the ‘‘ Additional Registration Statement ’’. For purposes of this Agreement, the following terms have the specified meanings:

‘‘ Applicable Time ’’ means 2:10 P.M. (New York City time) on the date of this Agreement;

‘‘ Base Prospectus ’’ means the base prospectus filed as part of the Registration Statement, in the form in which it has most recently been amended on or prior to the date hereof, relating to the Securities;

‘‘ Disclosure Package ’’ means, as of the Applicable Time, the most recent Preliminary Prospectus, together with each Issuer Free Writing Prospectus filed or used by the Company on or before the Applicable Time and identified on Schedule 2 hereto, other than a road show that is an Issuer Free Writing Prospectus under Rule 433 of the rules and regulations of the Commission (the ‘‘ Rules and Regulations ’’);

‘‘ Final Term Sheet ’’ means the term sheet prepared pursuant to Section 6(b) of the Agreement and substantially in the form attached in Schedule 3 hereto;

‘‘ Issuer Free Writing Prospectus ’’ means each ‘‘issuer free writing prospectus’’ (as defined in Rule 405 of the Rules and Regulations) prepared by or on behalf of the Company or used or referred to by the Company in connection with the offering of the Securities, including the Final Term Sheet;

‘‘ Preliminary Prospectus ’’ means any preliminary prospectus relating to the Securities, including the Base Prospectus and any preliminary prospectus supplement thereto, included in the Registration Statement or as filed with the Commission pursuant to Rule 424(b) (‘‘ Rule 424(b )’’) under the Act and provided to the Representatives for use by the Underwriters;

‘‘ Prospectus ’’ means the final prospectus relating to the Securities, including the Base Prospectus and the final prospectus supplement thereto relating to the Securities, as filed with the Commission pursuant to Rule 424(b) and provided to the Representatives for use by the Underwriters; and

‘‘ Registration Statement ’’ as of any time means the Initial Registration Statement and any Additional Registration Statement in the form then filed with the Commission, including any amendment thereto, any document incorporated by reference therein and any prospectus deemed or retroactively deemed to be a part thereof that has not been superseded or modified. ‘‘ Registration Statement ’’ without reference to a time means the Registration Statement as of the time of the first

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contract of sale for the Securities, which time shall be considered the ‘‘effective date’’ of the Registration Statement. For purposes of this definition, information contained in a form of prospectus or prospectus supplement that is deemed retroactively to be a part of the Registration Statement pursuant to Rule 430B shall be considered to be included in the Registration Statement as of the time specified in Rule 430B.

Any reference to the ‘‘ most recent Preliminary Prospectus ’’ will be deemed to refer to the latest Preliminary Prospectus included in the Registration Statement or filed pursuant to Rule 424(b) prior to or on the date hereof (including, for purposes of this Agreement, any documents incorporated by reference therein prior to or on the date of this Agreement). Any reference to any Preliminary Prospectus or the Prospectus will be deemed to refer to and include any documents incorporated by reference therein pursuant to Form S-3 under the Act as of the date of such Preliminary Prospectus or the Prospectus, as the case may be. Any reference to any amendment or supplement to any Preliminary Prospectus or the Prospectus will be deemed to refer to and include any document filed under the Securities Exchange Act of 1934, as amended (the ‘‘ Exchange Act ’’), after the date of such Preliminary Prospectus or the Prospectus, as the case may be, and incorporated by reference in such Preliminary Prospectus or the Prospectus, as the case may be.

(ii)    On the Effective Date of the Initial Registration Statement, the Initial Registration Statement conformed in all material respects to the requirements of the Act and the Rules and Regulations. On the Effective Date of the Additional Registration Statement (if any), each Registration Statement conformed, or will conform, in all material respects to the requirements of the Act and the Rules and Regulations. On the date of this Agreement, the Initial Registration Statement and, if the Effective Time of the Additional Registration Statement is prior to the execution and delivery of this Agreement, the Additional Registration Statement each conforms, the most recent Preliminary Prospectus conforms, and at the time of filing of the Prospectus pursuant to Rule 424(b) and as of the Closing Date, each Registration Statement and the Prospectus will conform, in all material respects to the requirements of the Act and the Rules and Regulations.

(iii)    The Company was at the time of filing of the Initial Registration Statement, and continues to be, a ‘‘well-known seasoned issuer’’ (as defined in Rule 405 of the Rules and Regulations) and was not since the time of the filing of the Initial Registration Statement, and continues not to be, an ‘‘ineligible issuer’’ (as defined in Rule 405 of the Rules and Regulations), in each case at all times relevant under the Act in connection with the offering of the Securities.

(iv)    Each Registration Statement did not, as of its Effective Date, contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein not misleading; provided, however , that no representation or warranty is made as to information contained in or omitted from the Registration Statement in reliance upon and in conformity with written information furnished to the Company through the Representatives by or on behalf of any Underwriter specifically for inclusion therein, it being understood that the only such information is that described as such in Section 8(b) hereof.

(v)    The Disclosure Package did not, as of the Applicable Time, does not, as of the date hereof, and will not, as of the Closing Date, contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading; provided, however , that no representation or warranty is made as to information contained in or omitted from the Disclosure Package in reliance upon and in conformity with written information furnished to the Company through the Representatives by or on behalf of any Underwriter specifically for inclusion therein, it being understood that the only such information is that described as such in Section 8(b) hereof.

(vi)    The Prospectus, and any amendment or supplement thereto, will not, as of its date and on the Closing Date, contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading; provided, however , that no representation or warranty is made as to information contained in or omitted from the Prospectus in reliance

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upon and in conformity with written information furnished to the Company through the Representatives by or on behalf of any Underwriter specifically for inclusion therein, it being understood that the only such information is that described as such in Section 8(b) hereof.

(vii)    The documents incorporated by reference in any Preliminary Prospectus or the Prospectus did not, and any further documents incorporated by reference therein will not, when filed with the Commission, contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading.

(viii)    The Commission has not issued any order preventing or suspending the effectiveness of the Registration Statement or preventing or suspending the use of any Preliminary Prospectus, any Issuer Free Writing Prospectus or the Prospectus; and no proceeding for any such purpose or pursuant to Section 8A of the Act against the Company or related to the offering of the Securities has been instituted or threatened by the Commission. The Commission has not issued any order directed to any document incorporated by reference in the most recent Preliminary Prospectus or the Prospectus, and no proceeding has been instituted or threatened by the Commission with respect to any document incorporated by reference in the most recent Preliminary Prospectus or the Prospectus. The Commission has not notified the Company of any objection to the use of the form of the Registration Statement.

(ix)    Each Issuer Free Writing Prospectus, as of its issue date and at all subsequent times through the completion of the public offer and sale of the Securities or until any earlier date that the Company notified or notifies the Representatives as described in the next sentence, did not, does not and will not include any information that conflicted, conflicts or will conflict with the information then contained in the Registration Statement, the most recent Preliminary Prospectus and the Prospectus. If at any time following issuance of an Issuer Free Writing Prospectus there occurred or occurs an event or development as a result of which such Issuer Free Writing Prospectus conflicted or would conflict with the information then contained in the Registration Statement or included or would include an untrue statement of a material fact or omitted or would omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances prevailing at that subsequent time, not misleading, (a) the Company has promptly notified or will promptly notify the Representatives and (b) the Company has promptly amended or will promptly amend or supplement such Issuer Free Writing Prospectus to eliminate or correct such conflict, untrue statement or omission. The foregoing two sentences do not apply to statements in or omissions from any Issuer Free Writing Prospectus in reliance upon and in conformity with written information furnished to the Company by any Underwriter through the Representatives specifically for use therein, it being understood and agreed that the only such information is that described as such in Section 8(b) hereof.

(x)    Neither the Company nor any of its subsidiaries has sustained since the date of the latest audited financial statements included or incorporated by reference in the Prospectus any material loss or interference with its business (exclusive of reinsurance treaties and insurance policies covering third-party risks) from fire, explosion, flood or other calamity, whether or not covered by insurance, or from any labor dispute or court or governmental action, order or decree, otherwise than as set forth or contemplated in the Prospectus; and, since the respective dates as of which information is given in any Registration Statement, the most recent Preliminary Prospectus and the Prospectus, there has not been any material adverse change in the capital stock, the capital or surplus or long-term debt of the Company or any of its subsidiaries or any material adverse change, or any development involving a prospective material adverse change, in or affecting the general affairs, management, financial position, shareholders’ equity or results of operations of the Company and its subsidiaries, otherwise than as set forth or contemplated in the most recent Preliminary Prospectus and the Prospectus.

(xi)    Neither the Company nor any of Aspen Insurance UK Limited (‘‘ Aspen U.K .’’), Aspen Insurance Limited (‘‘ Aspen Bermuda ’’) and Aspen Specialty Insurance Company (‘‘ Aspen U.S .’’ and, together with Aspen U.K. and Aspen Bermuda, the ‘‘ Designated Subsidiaries ’’) hold title to any real property; all of the leases, subleases and licenses under which the Company or any of its

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Designated Subsidiaries holds real properties described in the most recent Preliminary Prospectus and the Prospectus are in full force and effect, and neither the Company nor any Designated Subsidiary has any notice of any claim of any sort that has been asserted by anyone adverse to the rights of the Company or any Designated Subsidiary under any of the leases, subleases or licenses mentioned above, or affecting or questioning the rights of the Company or such Designated Subsidiary to the continued possession of the leased, subleased or licensed premises under any such lease or sublease, except where the failure to have such leases, subleases or licenses in full force and effect or the failure to have any such notice of any such claim would not, individually or in the aggregate, result in a material adverse change in the condition, financial or otherwise, or in the earnings, results of operations, business affairs, shareholders’ equity or business prospects of the Company and its subsidiaries, taken as a whole (a ‘‘ Material Adverse Effect ’’).

(xii)    The Company has been duly incorporated and is validly existing as an exempted company in good standing under the laws of Bermuda, with power and authority (corporate and other) to own its properties and conduct its business as described in the most recent Preliminary Prospectus and the Prospectus, and has been duly qualified as a foreign corporation for the transaction of business and is in good standing under the laws of each other jurisdiction in which it owns or leases properties or conducts any business so as to require such qualification, except where the failure to so qualify would not result in a Material Adverse Effect; each of the Designated Subsidiaries has been duly organized or incorporated and is validly existing as a company or corporation in good standing (including, in the case of Aspen Insurance Limited, as an exempted company) under the laws of its jurisdiction of organization or incorporation, with power and authority (corporate and other) to own its properties and conduct its business as described in the most recent Preliminary Prospectus and the Prospectus, and has been duly qualified as a foreign company or corporation for the transaction of business and is in good standing under the laws of each other jurisdiction in which it owns or leases properties or conducts any business so as to require such qualification, except where the failure to so qualify would not result in a Material Adverse Effect; and except for Aspen (UK) Holdings Limited (‘‘ Aspen U.K. Holdings ’’), Aspen Insurance UK Services Limited (‘‘ Aspen U.K. Services ’’), Aspen U.S. Holdings, Inc. (‘‘ Aspen U.S. Holdings ’’), Aspen Specialty Insurance Management Inc. (‘‘ Aspen Specialty ’’), Aspen Insurance U.S. Services Inc. (‘‘ Aspen U.S. Services ’’), AIUK Trustees Limited (‘‘ AIUK Trustees ’’) and Aspen Re America, Inc. (‘‘ Aspen Re America ’’), none of which, other than Aspen U.K. Holdings, is a ‘‘significant subsidiary’’ of the Company as that term is defined in Rule 1-02(w) of Regulation S-X of the Rules and Regulations, the Designated Subsidiaries are the only subsidiaries of the Company.

(xiii)    The Company has an authorized capitalization as set forth in the most recent Preliminary Prospectus and the Prospectus, and all of the issued shares of capital stock of the Company have been duly and validly authorized and issued, are fully paid and non-assessable and conform to the description of share capital contained in the Disclosure Package and the Prospectus; the Certificate of Designation has been duly and validly authorized by the Company; the Securities to be issued and sold by the Company to the Underwriters hereunder have been duly and validly authorized and, when issued and delivered against payment therefor as provided herein, will be duly and validly issued and fully paid and non-assessable and will conform to the description of the Preference Shares contained in the most recent Preliminary Prospectus and the Prospectus; and all of the currently issued and outstanding shares of capital stock of each subsidiary of the Company have been duly and validly authorized and issued, are fully paid and non-assessable and, except as set forth in the most recent Preliminary Prospectus and the Prospectus, are owned directly or indirectly by the Company, free and clear of all liens, encumbrances, equities or claims; the holders of outstanding shares of capital stock of the Company are not entitled to preemptive or other rights which have not been complied with; there are no outstanding securities convertible into or exchangeable for, or warrants, rights or options to purchase from the Company, or obligations of the Company to issue, Preference Shares or any other class of capital stock of the Company (except for (W) the options to purchase the Ordinary Shares issued to Wellington Underwriting plc (‘‘ Wellington ’’) and the options to purchase Ordinary Shares issued to the Appleby Trust (Bermuda) Limited, as trustee, which holds the securities for the members of Syndicate 2020 who are not corporate members of Wellington, (X) the

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options to purchase Ordinary Shares issued pursuant to the Company’s 2003 Share Incentive Plan, (Y) the options to purchase Ordinary Shares issued pursuant to the Company’s 2006 Stock Option Plan for Non-Employee Directors, and (Z) the conversion rights associated with the Company’s 5.625% Perpetual Preferred Income Equity Replacement Securities); except as disclosed in the most recent Preliminary Prospectus and the Prospectus, there are no restrictions on subsequent transfers of the Securities under the laws of Bermuda, as long as the Ordinary Shares are listed on the New York Stock Exchange (the ‘‘ NYSE ’’), and of the United States; and except as disclosed in the most recent Preliminary Prospectus and the Prospectus, no party has the right to require the Company to register securities.

(xiv)    This Agreement has been duly authorized, executed and delivered by the Company.

(xv)    There are no currency exchange control laws or withholding taxes, in the case of each of Bermuda or the United Kingdom (or any political subdivision or taxing authority thereof) that would be applicable to the payment of dividends (A) on the Securities by the Company (other than as may apply to residents of Bermuda for Bermuda exchange control purposes) or (B) by any of the Company’s subsidiaries to the Company; the Bermuda Monetary Authority (the ‘‘ BMA ’’) has designated the Company and Aspen Bermuda as non-resident for exchange control purposes and has granted permission for the issue and free transferability of the Securities pursuant to the Registration Statement, as long as the Ordinary Shares are listed on the NYSE, to and among persons who are non-residents of Bermuda for exchange control purposes (including permission for the issue and free transferability of up to 20% of the Securities to and among persons who are residents of Bermuda for exchange control purposes); such permission has not been revoked and is in full force and effect, and the Company has no knowledge of any proceedings planned or threatened for the revocation of such permission; the Company and Aspen Bermuda are ‘‘exempted companies’’ under Bermuda law and have not (V) acquired and do not hold any land for their respective business in Bermuda, other than that held by way of lease or tenancy for terms of not more than 50 years, without the express authorization of the Bermuda Minister of Finance, (W) acquired and do not hold land by way of lease or tenancy for terms of not more than 21 years in order to provide accommodation or recreational facilities for their officers and employees, without the express authority of the Bermuda Minister of Finance, (X) taken mortgages on land in Bermuda to secure an amount in excess of $50,000, without the consent of the Bermuda Minister of Finance, (Y) acquired any bonds or debentures secured by any land in Bermuda, except bonds or debentures issued by the government of Bermuda or a public authority of Bermuda, or (Z) conducted their business in a manner that is prohibited for ‘‘exempted companies’’ under Bermuda law; neither the Company nor Aspen Bermuda has received notification from the BMA or any other Bermuda governmental authority of proceedings relating to the modification or revocation of its designation as non-resident for exchange control purposes, its permission to issue and transfer the Preference Shares or its status as an ‘‘exempted company’’.

(xvi)    The issue and sale of the Securities to be sold by the Company hereunder, the execution, delivery and performance of this Agreement, the Certificate of Designation, the compliance by the Company with all of the provisions hereof and thereof and the consummation of the transactions contemplated hereby and thereby will not conflict with or result in a breach or violation of any of the terms or provisions of, or constitute a default under, (A) the certificate of incorporation, memorandum of association, articles of association, bye-laws, by-laws or other organizational document, as amended (any such document, a ‘‘ Constitutional Document ’’), as the case may be, of the Company or any of its subsidiaries, (B) any indenture, mortgage, deed of trust, loan agreement or other agreement or instrument to which the Company or any of its subsidiaries is a party or by which the Company or any of its subsidiaries is bound or to which any of the property or assets of the Company or any of its subsidiaries is subject, or (C) any statute or any order, rule or regulation of any court or governmental agency or body, any stock exchange authority or any other regulatory authority (hereinafter referred to as a ‘‘ Governmental Agency ’’) having jurisdiction over the Company or any of its subsidiaries or any of their properties, except, in the case of clause (C), as would not, individually or in the aggregate, result in a Material Adverse Effect.

(xvii)    No consent, approval, authorization, order, registration or qualification of or with any Governmental Agency (hereinafter referred to as the ‘‘ Governmental Authorizations ’’) is required

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for the issue and sale of the Securities or the consummation by the Company of the transactions contemplated hereby, except (A) the registration under the Act of the Securities, (B) such Governmental Authorizations as have been duly obtained and are in full force and effect and copies of which have been furnished to the Representatives, (C) such Governmental Authorizations as may be required under state securities laws, Blue Sky laws, insurance securities laws or any laws of jurisdictions outside the United States in connection with the purchase and distribution of the Securities by or for the respective accounts of the Underwriters, (D) such consents, approvals or authorizations required by the NYSE in connection with the listing of the Securities, (E) the filing of the Prospectus with the Registrar of Companies in Bermuda in accordance with Bermuda law and (F) such consents, approvals, authorizations, registrations or qualifications as may be required and have been obtained from the BMA.

(xviii)    Neither the Company nor any of the Designated Subsidiaries is (A) in violation of any of its Constitutional Documents or (B) in default in the performance or observance of any obligation, agreement, covenant or condition contained in any indenture, mortgage, deed of trust, loan agreement, lease or other agreement, or instrument to which it is a party or by which it or any of its properties may be bound, except, in the case of clause (B), for any such defaults or violations that would not, individually or in the aggregate, result in a Material Adverse Effect or as otherwise waived or consented to by the parties or shareholders to which the Company or the Designated Subsidiaries owes any obligations under such agreements or documents.

(xix)    No stamp or other issuance or transfer taxes or duties and no capital gains, income, withholding or other taxes are payable by or on behalf of any Underwriter to Bermuda or any political subdivision or taxing authority thereof or therein in connection with (A) the sale and delivery of the Securities to or for the respective accounts of the Underwriters or (B) the sale and delivery outside Bermuda by the Underwriters of the Securities to the initial purchasers thereof.

(xx)    Except as disclosed in the most recent Preliminary Prospectus and the Prospectus, the Company has no knowledge of any threatened or pending downgrading of the rating accorded the debt securities or preferred shares of the Company or the financial strength or claims-paying ability of the Company or any of the Designated Subsidiaries by A.M. Best Company, Inc., Standard & Poor’s Ratings Service, a Division of The McGraw-Hill Companies, Inc. (‘‘ S&P ’’), or Moody’s Investors Services, Inc. (‘‘ Moody’s ’’) (collectively, the ‘‘ Ratings Agencies ’’ and, individually, a ‘‘ Rating Agency ’’). The Ratings Agencies are the only ‘‘nationally recognized statistical rating organizations,’’ as that term is defined by the Commission for purposes of Rule 463(g)(2) under the Act, which currently rate the debt securities or preferred shares of the Company or the financial strength or claims-paying ability of the Company or any of the Designated Subsidiaries. None of the Ratings Agencies and no other nationally recognized statistical rating organization currently rates any other securities of the Company or any securities of its subsidiaries.

(xxi)    There are no legal or governmental proceedings pending to which the Company or any of its subsidiaries is a party or of which any property of the Company or any of its subsidiaries is the subject which, if determined adversely to the Company or any of its subsidiaries, would, individually or in the aggregate, result in a Material Adverse Effect; and, to the best of the Company’s knowledge, no such proceedings are threatened or contemplated by any Governmental Agency or threatened by others.

(xxii)    The Company is not and, after giving effect to the offering and sale of the Securities and the application of the net proceeds from such sale as described in the most recent Preliminary Prospectus and the Prospectus under the caption ‘‘Use of Proceeds’’, will not be an ‘‘investment company’’ as defined in the Investment Company Act of 1940, as amended.

(xxiii)    Each of the Designated Subsidiaries and Aspen Specialty is duly licensed as an insurance brokerage company, insurer or reinsurer, as the case may be, under the insurance laws and the rules, regulations and interpretations of the insurance regulatory authorities thereunder (collectively, ‘‘ Insurance Laws ’’) of each jurisdiction in which the conduct of its existing business as described in the most recent Preliminary Prospectus and the Prospectus requires such licensing, except for such jurisdictions in which the failure to be so licensed would not, individually or in the

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aggregate, result in a Material Adverse Effect; each of the Company, the Designated Subsidiaries and Aspen Specialty has made all required filings under applicable holding company statutes or other Insurance Laws in each jurisdiction where such filings are required, except for such jurisdictions in which the failure to make such filings would not, individually or in the aggregate, result in a Material Adverse Effect; except as described in the most recent Preliminary Prospectus and the Prospectus, each of the Company, the Designated Subsidiaries and Aspen Specialty has all other necessary authorizations, approvals, orders, consents, certificates, licenses, permits, registrations and qualifications of and from all insurance regulatory authorities necessary to conduct their respective existing businesses as described in the most recent Preliminary Prospectus and the Prospectus and all of the foregoing are in full force and effect, except where the failure to have such authorizations, approvals, orders, consents, certificates, permits, registrations or qualifications or their failure to be in full force and effect would not, individually or in the aggregate, result in a Material Adverse Effect; none of the Company, the Designated Subsidiaries or Aspen Specialty has received any notification from any insurance regulatory authority or other governmental authority in the United States, Bermuda, the United Kingdom or elsewhere to the effect that any additional authorization, approval, order, consent, certificate, permit, registration or qualification is needed to be obtained by either the Company, the Designated Subsidiaries or Aspen Specialty to conduct its existing business as described in the most recent Preliminary Prospectus and the Prospectus; and except as otherwise described in the most recent Preliminary Prospectus and the Prospectus, no insurance regulatory authority has issued any order or decree impairing, restricting or prohibiting the payment of dividends by the Company or any of the Designated Subsidiaries.

(xxiv)    Each of the Company and the Designated Subsidiaries maintains a system of internal accounting controls sufficient to provide reasonable assurance that (A) transactions are executed in accordance with management’s general or specific authorizations, (B) transactions are recorded as necessary to permit preparation of financial statements in conformity with generally accepted accounting principles and to maintain asset accountability, (C) access to assets is permitted only in accordance with management’s general or specific authorization, and (D) assets as recorded are compared with the existing assets at reasonable intervals and appropriate action is taken with respect to any differences.

(xxv)    Each of the Company and the Designated Subsidiaries has filed all statutory financial returns, reports, documents and other information required to be filed pursuant to the applicable Insurance Laws of the United States and the various states thereof, Bermuda, the United Kingdom and each other jurisdiction applicable thereto, except where the failure, individually or in the aggregate, to file such return, report, document or information would not result in a Material Adverse Effect; and each of the Company and the Designated Subsidiaries maintains its books and records in accordance with, and is otherwise in compliance with, the applicable Insurance Laws of the United States and the various states thereof, Bermuda, the United Kingdom and each other jurisdiction applicable thereto, except where the failure to so maintain its books and records or be in compliance would not, individually or in the aggregate, result in a Material Adverse Effect.

(xxvi)    (A) Any tax returns required to be filed by the Company or any of its subsidiaries, other than Aspen U.S., Aspen U.K. and Aspen U.K. Services, in any jurisdiction have been accurately prepared and timely filed and any taxes, including any withholding taxes, excise taxes, franchise taxes and similar fees, sales taxes, use taxes, penalties and interest, assessments and fees and other charges due or claimed to be due from such entities have been paid, other than any of those being contested in good faith and for which adequate reserves have been provided or any of those currently payable without penalty or interest and (B) to the Company’s knowledge, any tax returns required to be filed by Aspen U.S., Aspen U.K. and Aspen U.K. Services in any jurisdiction have been accurately prepared and timely filed and any taxes, including any withholding taxes, excise taxes, franchise taxes and similar fees, sales taxes, use taxes, penalties and interest, assessments and fees and other charges due or claimed to be due from Aspen U.S. have been paid, other than any of those being contested in good faith and for which adequate reserves have been provided or any of those currently payable without penalty or interest, in either case (1) except to the extent that the failure to so file or pay would not result in a Material Adverse Effect and (2) other than those tax returns that would be

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required to be filed or taxes that would be payable by the Company or any of its subsidiaries if (a) any of them was characterized as a ‘‘personal holding company’’ as defined in Section 542 of the Internal Revenue Code of 1986, as amended (the ‘‘ Code ’’), (b) any of them other than Aspen Specialty, Aspen U.S., Aspen U.S. Holdings, Aspen U.S. Services and Aspen Re America (collectively, the ‘‘ U.S. Subsidiaries ’’) was characterized as engaged in a U.S. trade or business, and (c) any of them other than Aspen U.K., Aspen U.K. Holdings, AIUK Trustees and Aspen U.K. Services (collectively, the ‘‘ U.K. Subsidiaries ’’) was characterized as resident, managed and controlled or carrying on a trade through a branch or agency in the United Kingdom; no deficiency assessment with respect to a proposed adjustment of the Company’s or any of its subsidiaries’ taxes is pending or, to the best of the Company’s knowledge, threatened; and there is no tax lien, whether imposed by any federal, state, or other taxing authority, outstanding against the assets, properties or business of the Company or any of its subsidiaries, in either case, which would have a Material Adverse Effect.

(xxvii)       Each of the Company and Aspen Bermuda have received from the Bermuda Minister of Finance an assurance under the Exempted Undertakings Tax Protection Act 1966, as amended, of Bermuda to the effect set forth in the most recent Preliminary Prospectus and the Prospectus under the caption ‘‘Material Tax Considerations — Taxation of Aspen Holdings and Subsidiaries — Bermuda,’’ and the Company has not received any notification to the effect (and is not otherwise aware) that such assurance may be revoked or otherwise not honored by the Bermuda government.

(xxviii)    Based upon and subject to the assumptions and qualifications set forth in the most recent Preliminary Prospectus and the Prospectus under the caption ‘‘Material Tax Considerations,’’ the Company does not believe (A) that either the Company or any of its subsidiaries currently should be, or upon the sale of the Securities contemplated hereby should be, (1) treated as a ‘‘passive foreign investment company’’ as defined in Section 1297(a) of the Code, (2) characterized as a ‘‘personal holding company’’ as defined in Section 542 of the Code, (3) except for the U.S. Subsidiaries, considered to be engaged in a trade or business within the United States for purposes of Section 864(b) of the Code (although the Internal Revenue Service may be able to successfully assert that Aspen U.K. has a U.S. trade or business and a U.S. permanent establishment as a result of the binding authorities previously granted to Wellington Underwriting Inc. by Aspen U.K. and likely will be able to successfully assert that Aspen U.K. has a U.S. trade or business and a permanent establishment as a result of the binding authorities granted to Aspen Re America by Aspen U.K.), or (4) except for the U.K. Subsidiaries, characterized as resident, managed or controlled or carrying on a trade through a branch or agency in the United Kingdom or (B) that any U.S. person who owns shares of capital of the Company directly or indirectly through foreign entities should be treated as owning (directly, indirectly through foreign entities or by attribution pursuant to Section 958(b) of the Code) 10% or more of the total voting power of the Company or any of its foreign subsidiaries; and to the best of the Company’s knowledge, in the event that the Internal Revenue Service were to be successful in asserting that Aspen U.K. has a U.S. trade or business as a result of the binding authorities previously granted to Wellington Underwriting Inc. and Aspen Re America by Aspen U.K., it would not result in a Material Adverse Effect.

(xxix)    Aspen U.K. and Aspen Bermuda intend to operate in a manner that is intended to ensure that the ‘‘related person insurance income’’ (as defined in Section 953(c)(2) of the Code) of either of Aspen U.K. or Aspen Bermuda does not equal or exceed 20% of each such company’s gross insurance income for any taxable year in the foreseeable future.

(xxx)     The audited consolidated financial statements included or incorporated by reference in the Registration Statement, the most recent Preliminary Prospectus and the Prospectus, together with the related schedules and notes, present fairly, in all material respects, the financial position of the Company and its consolidated subsidiaries at the dates indicated and the statement of operations, shareholders’ equity and cash flows of the Company and its consolidated subsidiaries for the periods specified; except as otherwise disclosed in the Registration Statement, the most recent Preliminary Prospectus and the Prospectus, said consolidated financial statements have been prepared in conformity with generally accepted accounting principles in the United States (‘‘ U.S. GAAP ’’) applied on a consistent basis throughout the periods involved; the supporting schedules included or

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incorporated by reference in the Registration Statement, the most recent Preliminary Prospectus or the Prospectus present fairly, in all material respects, in accordance with U.S. GAAP, the information required to be stated therein; and the selected financial data and the summary financial information included or incorporated by reference in the Registration Statement, the most recent Preliminary Prospectus and Prospectus present fairly, in all material respects, the information shown therein and have been compiled on a basis consistent with that of the audited financial statements included or incorporated by reference in the Registration Statement.

(xxxi)        KPMG Audit plc, who has certified certain financial statements of the Company and its subsidiaries, is an independent public accountant as required by the Act and the Rules and Regulations.

(xxxii)     The Company is subject to the reporting requirements of either Section 13 or Section 15(d) of the Exchange Act and files reports with the Commission on the Electronic Data Gathering, Analysis, and Retrieval (EDGAR) system.

(xxxiii)     The Company and, to the knowledge of the Company, the Company’s directors and officers, in their capacities as such, are in compliance with the currently applicable provisions of the Sarbanes-Oxley Act of 2002.

(xxxiv)     No action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving the Company or any of its subsidiaries with respect to applicable financial recordkeeping and reporting requirements of the Currency and Foreign Transactions Reporting Act of 1970, as amended, the money laundering statutes of all jurisdictions, the rules and regulations thereunder and any related or similar rules, regulations or guidelines, issued, administered or enforced by any governmental agency is pending or, to the knowledge of the Company, threatened.

(xxxv)     The Company will not directly or indirectly use the proceeds of the offering, or lend, contribute or otherwise make available such proceeds to any subsidiary, joint venture partner or other person or entity, for the purpose of financing the activities of any person currently subject to any U.S. sanctions administered by the Office of Foreign Assets Control of the U.S. Treasury Department.

(xxxvi)     On the Closing Date (A) the Securities shall have been approved for listing, subject to official notice of issuance, on the NYSE and (B) the Preference Shares shall have been registered pursuant to Section 12 of the Exchange Act.

For purposes of this Section 2, as well as for Section 7 hereof, references to ‘‘the most recent Preliminary Prospectus and the Prospectus’’ or ‘‘the Disclosure Package and the Prospectus’’ are to each of the most recent Preliminary Prospectus or the Disclosure Package, as the case may be, and the Prospectus as separate or stand-alone documentation (and not the most recent Preliminary Prospectus or the Disclosure Package, as the case may be, and the Prospectus taken together), so that representations, warranties, agreements, conditions and legal opinions will be made, given or measured independently in respect of each of the most recent Preliminary Prospectus or the Disclosure Package, as the case may be, and the Prospectus.

3.         Purchase, Sale and Delivery of Securities.     On the basis of the representations, warranties and agreements herein contained, but subject to the terms and conditions herein set forth, the Company agrees to issue and sell to the Underwriters, and each of the Underwriters agrees, severally and not jointly, to purchase from the Company, at a purchase price of $24.6625 per Preference Share, the number of Preference Shares set forth opposite such Underwriter’s name in Schedule 1 hereto.

The Company will deliver the Securities to the Representatives for the respective accounts of the Underwriters, through the facilities of The Depository Trust Company (‘‘ DTC ’’) against payment of the purchase price in federal (same day) funds by official bank check or checks or wire transfer to an account at a bank acceptable to the Representatives drawn to the order of the Company at 9:30 a.m., New York City time, on November 15, 2006 or at such other time not later than seven full business days thereafter as the Representatives and the Company determine, such time being herein referred to as the ‘‘ Closing

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Date ’’. The certificates for the Securities so to be delivered will be in definitive form, in such denominations and registered in such names as the Representatives request and will be made available for checking and packaging at the office of Simpson Thacher & Bartlett LLP, 425 Lexington Avenue, New York, New York 10017 at least 24 hours prior to the Closing Date.

4.         Offering by Underwriters .

(a)    It is understood that each of the several Underwriters proposes to offer the Securities for sale to the public as set forth in the Prospectus.

(b)    Each Underwriter represents and agrees, severally and not jointly, that in relation to each Member State of the European Economic Area which has implemented the Prospectus Directive (each, a ‘‘ Relevant Member State ’’), with effect from and including the date on which the Prospectus Directive is implemented in that Relevant Member State (the ‘‘ Relevant Implementation Date ’’) such Underwriter has not made and will not make an offer of the Preference Shares to the public in that Relevant Member State prior to the publication of a prospectus in relation to the Preference Shares which has been approved by the competent authority in that Relevant Member State or, where appropriate, approved in another Relevant Member State and notified to the competent authority in that Relevant Member State, all in accordance with the Prospectus Directive, except that it may, with effect from and including the Relevant Implementation Date, make an offer of Preference Shares to the public in that Relevant Member State at any time:

(i)    to legal entities which are authorised or regulated to operate in the financial markets or, if not so authorised or regulated, whose corporate purpose is solely to invest in securities;

(ii)    to any legal entity which has two or more of (1) an average of at least 250 employees during the last financial year; (2) a total balance sheet of more than €43,000,000 and (3) an annual net turnover of more than €50,000,000, as shown in its last annual or consolidated accounts;

(iii)    to fewer than 100 natural or legal persons (other than qualified investors as defined in the Prospectus Directive); or

(iv)    in any other circumstances which do not require the publication by the Company of a prospectus pursuant to Article 3 of the Prospectus Directive.

For the purposes of this provision, the expression an ‘‘offer of Preference Shares to the public’’ in relation to any Preference Shares in any Relevant Member State means the communication in any form and by any means of sufficient information on the terms of the offer and the Preference Shares to be offered so as to enable an investor to decide to purchase or subscribe the Preference Shares, as the same may be varied in that Member State by any measure implementing the Prospectus Directive in that Member State and the expression ‘‘Prospectus Directive’’ means Directive 2003/71/EC of the European Parliament and of the Council and includes any relevant implementing measure in each Relevant Member State.

(c)    Each Underwriter severally, but not jointly, represents and agrees that:

(i)    (A) it is a person whose ordinary activities involve it in acquiring, holding, managing or disposing of investments (as principal or agent) for the purposes of its business and (B) it has not offered or sold and will not offer or sell any Preference Shares other than to persons whose ordinary activities involve them in acquiring, holding, managing or disposing of investments (as principal or as agent) for the purposes of their businesses or who it is reasonable to expect will acquire, hold, manage or dispose of investments (as principal or agent) for the purposes of their businesses where the issue of the Preference Shares would otherwise constitute a contravention of Section 19 of the Financial Services and Markets Act 2000, as amended (‘‘ FSMA ’’) by the Company;

(ii)    it has only communicated or caused to be communicated and will only communicate or cause to be communicated an invitation or inducement to engage in investment activity (within the meaning of Section 21 of the FSMA) received by it in connection with the issue or sale of the Preference Shares in circumstances in which Section 21(1) of the FSMA does not apply to the Company; and

(iii)    it has complied and will comply with all applicable provisions of the FSMA with respect to anything done by it in relation to any such Preference Shares in, from or otherwise involving the United Kingdom.

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5.         Certain Agreements of the Company and the Underwriters .

(a)    The Company covenants and agrees with each Underwriter that:

(i)    The Company has filed or will file each Preliminary Prospectus and the Prospectus pursuant to and in accordance with Rule 424(b)(2) (or, if applicable and consented to by the Representatives, subparagraph (5)) not later than the second business day following the earlier of the date it is first used or the date of this Agreement. The Company has complied and will comply with Rule 433.

(ii)    The Company will prepare and file the Prospectus pursuant to and in accordance with Rule 424(b)(2) (or, if applicable and consented to by the Representatives, subparagraph (5)) not later than the second business day following the date of this Agreement.

(iii)    If an additional registration statement is necessary to register a portion of the Securities under the Act but the Effective Time thereof has not occurred as of the execution and delivery of this Agreement, the Company will file the additional registration statement or, if the additional registration statement has been filed, will file a post-effective amendment thereto with the Commission pursuant to and in accordance with Rule 462(b) (if available) on or prior to 10:00 P.M., New York City time, on the date of this Agreement or, if earlier, on or prior to the time the Prospectus is printed and distributed to any Underwriter, or will make such filing at such later date as shall have been consented to by the Representatives.

(iv)    The Company will advise the Representatives promptly of any proposal to amend or supplement the initial or any additional registration statement as filed or the related prospectus or the Initial Registration Statement, the Additional Registration Statement (if any), any Preliminary Prospectus or the Prospectus and will not effect any such amendment or supplementation that shall be disapproved by the Representatives promptly after reasonable notice thereof. The Company will also advise the Representatives promptly of the effectiveness of each Registration Statement (if its Effective Time is subsequent to the execution and delivery of this Agreement), of any amendment or supplementation of a Registration Statement, any Preliminary Prospectus or the Prospectus, of the institution by the Commission or any state or other regulatory body of any stop order or any order suspending the effectiveness of the Registration Statement, suspending or preventing the use of any Preliminary Prospectus, the Prospectus or any Issuer Free Writing Prospectus, of the suspension of the qualification of the Securities for offering or sale in any jurisdiction, of the initiation or threatening of any proceeding for any such purpose or of any request by the Commission for the amending or supplementing of a Registration Statement or for additional information. In the event of the issuance of any such stop order or any order suspending any such qualification, the Company will promptly use its reasonable best efforts to obtain the withdrawal of such order.

(v)    If, at any time when a prospectus relating to the Securities is (or but for the exemption in Rule 172 would be required to be) delivered under the Act in connection with sales by any Underwriter or dealer, any event occurs as a result of which the Prospectus as then amended or supplemented would include an untrue statement of a material fact or omit to state any material fact necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading, or if it is necessary at any time to amend any Preliminary Prospectus or the Prospectus to comply with the Act, the Company will promptly notify the Representatives of such event and will promptly prepare and file with the Commission, at its own expense, an amendment or supplement which will correct such statement or omission or an amendment which will effect such compliance. Neither the Representatives’ consent to, nor the Underwriters’ delivery of, any such amendment or supplement shall constitute a waiver of any of the conditions set forth in Section 6.

(vi)    As soon as practicable, but not later than 16 months, after the date of this Agreement, the Company will make generally available to its securityholders an earnings statement (which need not be audited) covering a period of at least 12 months beginning after the date of this Agreement and satisfying the provisions of Section 11(a) of the Act and Rule 158 of the Rules and Regulations.

(vii)    The Company will furnish to the Representatives copies of each Registration Statement (three of which will be signed and will include all exhibits), each related Preliminary Prospectus, and, so long as a prospectus relating to the Securities is (or but for the exemption in Rule 172 would be

12




required to be) delivered under the Act in connection with sales by any Underwriter or dealer, the Prospectus and all amendments and supplements to such documents, in each case in such quantities as the Representatives reasonably request. The Prospectus shall be so furnished on or prior to 10:00 A.M., New York City time, on the business day following the delivery of this Agreement. All other such documents shall be so furnished as soon as available.

(viii)    The Company will arrange for the qualification of the Securities for sale under the laws of such jurisdictions as the Representatives reasonably designate and will continue such qualifications in effect so long as required for the distribution; provided, however , that, in connection therewith, the Company shall not be required to qualify as a foreign company or corporation or as a dealer in securities in any jurisdiction in which it is not so qualified, or to file a general consent to service of process in any jurisdiction, or to subject itself to material taxation in respect of doing business in any jurisdiction in which it is not otherwise so subject.

(ix)    The Company will use its commercially reasonable efforts to complete the listing of the Preference Shares on the NYSE.

(x)    The Company will use its commercially reasonable efforts to permit the Preference Shares to be eligible for ‘‘book-entry’’ transfer through the facilities of DTC.

(xi)    Until 60 days following the Closing Date, the Company will not, without the prior written consent of the Representatives, directly or indirectly, issue, sell, offer to sell, grant any option for the sale or otherwise dispose of any series of preference shares or securities convertible into or exchangeable or exercisable for any series of preference shares of the Company; provided , however , that the foregoing will not apply to issuances to raise funds as a result of a large loss event impacting the Company’s reinsurance or insurance portfolio or, where, in the good faith of judgment of the Company’s management, such additional funds are necessary to maintain to Company’s existing ratings or ratings outlook.

(xii)    The Company agrees to pay or cause to be paid all expenses incident to the performance of its obligations under this Agreement, including (A) the fees and disbursements of the Company’s counsel and the Company’s accountants in connection with the registration of the Securities under the Act and all other fees or expenses in connection with the preparation and filing of the Registration Statement, any Preliminary Prospectus, the Prospectus and amendments and supplements to any of the foregoing, including the costs of printing and distributing copies of all such documents to the Underwriters and dealers, in the quantities specified herein, (B) expenses incurred for preparing, printing and distributing any Issuer Free Writing Prospectuses to investors or prospective investors, (C) any filing fees and other expenses (including the reasonable fees and disbursements of counsel) incurred in connection with qualification of the Securities for sale under the laws of such jurisdictions as the Representatives designate and the printing of memoranda relating thereto, (D) any fees charged by investment rating agencies for the rating of the Securities, (E) all expenses and fees in connection with the application for listing of the Securities on the NYSE, (F) the costs and charges of any registrar, transfer agent, paying agent and calculation agent, (G) the filing fee incident to the review by the National Association of Securities Dealers, Inc. of the Securities and (H) any travel expenses of the Company’s officers and employees and any other expenses of the Company in connection with attending or hosting meetings with prospective purchasers of the Securities, including the cost of any aircraft chartered in connection with attending or hosting such meetings.

(b)    (i) The Underwriters, severally but not jointly, agree with the Company that, except as provided in this Section 5, Section 10 and the provisions with respect to indemnity and contribution, the Underwriters will pay all of their costs and expenses, including fees and disbursements of their counsel, share transfer taxes payable on resale of any of the Securities by them and any advertising expenses connected with any offers they may make.

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6.         Free Writing Prospectuses.

(a)    The Company represents and warrants to, and agrees with, each Underwriter that (i) the Company has not made, and will not, make any offer relating to the Securities that would constitute an Issuer Free Writing Prospectus without the prior consent of the Representatives (which consent being deemed to have been given with respect to (A) the Final Term Sheet prepared and filed pursuant to Section 6(b) hereof and (B) any other Issuer Free Writing Prospectus identified on Schedule 2 hereto) and (ii) each Issuer Free Writing Prospectus conformed or will conform in all material respects to the requirements of the Act and the Rules and Regulations on the date of first use, and the Company has complied or will comply with any filing requirements applicable to such Issuer Free Writing Prospectus pursuant to Rule 433 of the Rules and Regulations.

(b)    The Company will prepare the Final Term Sheet, substantially in the form of Schedule 3 hereto and approved by the Representatives and file the Final Term Sheet pursuant to Rule 433(d) of the Rules and Regulations within the time period prescribed by such rule.

(c)    Each Underwriter severally, but not jointly, represents and warrants to, and agrees with, the Company and each other Underwriter that it has not made, and will not make any offer relating to the Preference Shares that would constitute a ‘‘free writing prospectus’’ (as defined in Rule 405 of the Rules and Regulations) required to be filed with the Commission, without the prior consent of the Company and the Representatives.

7.         Conditions of the Obligations of the Underwriters.     The obligations of the several Underwriters to purchase and pay for the Securities on the Closing Date will be subject to the accuracy of the representations and warranties on the part of the Company herein, to the accuracy of the statements of Company officers made pursuant to the provisions hereof, to the performance by the Company of its obligations hereunder and to the following additional conditions precedent:

(a)    Concurrently with the execution of this Agreement, the Representatives shall have received from KPMG Audit plc, the Company’s independent registered public accounting firm, a ‘‘comfort’’ letter (the ‘‘ initial comfort letter ’’) addressed to the Representatives on behalf of the Underwriters, dated the date hereof, and in form and substance satisfactory to the Representatives.

(b)    The Representatives shall have received a ‘‘bring-down comfort’’ letter (the ‘‘ bring-down comfort letter ’’) from KPMG Audit plc, the Company’s independent registered public accounting firm, addressed to the Representatives.

(c)    If the Effective Time of the Additional Registration Statement (if any) is not prior to the execution and delivery of this Agreement, such Effective Time shall have occurred not later than 10:00 P.M., New York City time, on the date of this Agreement or, if earlier, the time the Prospectus is printed and distributed to any Underwriter, or shall have occurred at such later date as shall have been consented to by the Representatives. The Prospectus shall have been filed with the Commission in accordance with the Rules and Regulations and Section 5(a) of this Agreement; all filings (including, without limitation, the Final Term Sheet) required by Rule 424(b) or Rule 433 of the Rules and Regulations shall have been made within the time periods prescribed by such rules, and no such filings will have been made without the consent of the Representatives. Prior to the Closing Date, no stop order suspending the effectiveness of a Registration Statement or any amendment or supplement thereto, preventing or suspending the use of any Preliminary Prospectus, any Issuer Free Writing Prospectus or the Prospectus, shall have been issued and no proceedings for that purpose shall have been instituted or threatened by the Commission; no proceedings for the issuance of such order shall have been initiated or threatened pursuant to Section 8A of the Act; no notice of objection of the Commission to use any Registration Statement or any post-effective amendment thereto shall have been received by the Company; and any request for additional information on the part of the Commission shall have been complied with to the Representatives’ reasonable satisfaction.

(d)    Subsequent to the execution and delivery of this Agreement, there shall not have occurred (i) any change, or any development or event involving a prospective change, in the condition (financial or other), business, properties or results of operations of the Company or its subsidiaries which, in the judgment of the Representatives, is material and adverse and makes it impractical or inadvisable to

14




proceed with completion of the public offering or the sale of and payment for the Securities; (ii) any downgrading in the rating of any debt securities, preferred shares, financial strength or claims paying ability of the Company or any of the Designated Subsidiaries by any ‘‘nationally recognized statistical rating organization’’ (as defined for purposes of Rule 436(g) under the Act), or any public announcement that any such organization has under surveillance or review its rating of any debt securities or preferred shares of the Company (other than an announcement with positive implications of a possible upgrading, and no implication of a possible downgrading, of such rating) or any announcement that the Company has been placed on negative outlook; (iii) any change in U.S., U.K., Bermudian or international financial, political or economic conditions or currency exchange rates or exchange controls as would, in the judgment of the Representatives, be likely to prejudice materially the success of the proposed issue, sale or distribution of the Securities, whether in the primary market or in respect of dealings in the secondary market; (iv) any material suspension or material limitation of trading in securities generally on the NYSE, or any setting of minimum prices for trading on such exchange; (v) or any suspension of trading of any securities of the Company on any exchange or in the over-the-counter market; (vi) any banking moratorium declared by United States federal, New York, U.K. or Bermudian authorities; (vii) a change or development involving a prospective change in Bermuda taxation affecting the Company, the Preference Shares or transfers thereof; (viii) any major disruption of settlements of securities or clearance services in the United States, United Kingdom or Bermuda or (ix) any attack on, outbreak or escalation of hostilities or act of terrorism involving the United States, the United Kingdom or Bermuda, any declaration of war by Congress or any other national or international calamity or emergency if, in the judgment of the Representatives, the effect of any such attack, outbreak, escalation, act, declaration, calamity or emergency makes it impractical or inadvisable to proceed with completion of the public offering or the sale of and payment for the Securities.

(e)    The Underwriters shall have received an opinion, dated the Closing Date, of LeBoeuf, Lamb, Greene & MacRae LLP, special U.S. counsel for the Company in the form of Annex I-A hereto and a letter in the form of Annex I-B hereto.

(f)    The Underwriters shall have received an opinion, dated the Closing Date, of Appleby Hunter Bailhache, Bermuda counsel for the Company in the form of Annex II hereto.

(g)    The Underwriters shall have received an opinion, dated the Closing Date, of LeBoeuf, Lamb, Greene & MacRae, U.K. counsel for the Company, in the form of Annex III hereto.

(h)    The Underwriters shall have received an opinion, dated the Closing Date, of David Curtin, General Counsel to the Company, in the form of Annex IV hereto.

(i)    The Underwriters shall have received from Simpson Thacher & Bartlett LLP, counsel for the Underwriters, such opinion or opinions, dated the Closing Date, with respect to the Registration Statements, the Prospectus and other related matters as the Underwriters may require, and the Company shall have furnished to such counsel such documents as they request for the purpose of enabling them to pass upon such matters.

(j)    The Underwriters shall have received a certificate or certificates, dated the Closing Date, of the Chief Executive Officer and the Chief Financial Officer of the Company in which such officers, to the best of their knowledge after reasonable investigation, shall state that: the representations and warranties of the Company in this Agreement are true and correct; the Company has complied with all agreements and satisfied all conditions on its part to be performed or satisfied hereunder at or prior to the Closing Date; no stop order suspending the effectiveness of any Registration Statement has been issued and no proceedings for that purpose have been instituted or are contemplated by the Commission; the Additional Registration Statement (if any) satisfying the requirements of subparagraphs (1) and (3) of Rule 462(b) was filed pursuant to Rule 462(b), including payment of the applicable filing fee in accordance with Rule 111(a) or (b) under the Act, prior to the time the Prospectus was printed and distributed to any Underwriter; and, subsequent to the date of the most recent financial statements in the most recent Preliminary Prospectus and the Prospectus, there has been no material adverse change, or any development or event involving a prospective material adverse change, in the condition (financial or

15




other), business, properties or results of operations of the Company and its subsidiaries taken as a whole except as set forth in the most recent Preliminary Prospectus and the Prospectus or as described in such certificate.

(k)    The Company shall have provided the Underwriters with copies of such additional opinions, certificates, letters and documents as the Underwriters reasonably request.

(l)    The NYSE shall have approved the Securities for listing, subject only to official notice of issuance.

(m)    On the Closing Date the Preference Shares shall be rated at least ‘‘Ba1’’ by Moody’s and ‘‘BBB−’’ by S&P, and each such rating agency shall have delivered to the Representatives a letter, or other evidence satisfactory to the Representatives, confirming that the Preference Shares have such ratings.

(n)    At the Closing Date, counsel for the Underwriters shall have been furnished with such documents and opinions as they may reasonably require for the purpose of enabling them to pass upon the issuance and sale of the Securities as herein contemplated, or in order to evidence the accuracy of any of the representations or warranties, or the fulfillment of any of the conditions, herein contained; and all proceedings taken by the Company in connection with the issuance and sale of the Securities as herein contemplated shall be reasonably satisfactory in form and substance to the Representatives and counsel for the Underwriters.

(o)    If any condition specified in this Section shall not have been fulfilled when and as required to be fulfilled, this Agreement may be terminated by the Representatives by notice to the Company at any time at or prior to the Closing Date and such termination shall be without liability of any party to any other party except as provided in Section 5(a)(xii) and except that Sections 2, 8 and 10 shall survive any such termination and remain in full force and effect.

The Representatives may in their sole discretion waive on behalf of the Underwriters compliance with any conditions to the obligations of the Underwriters hereunder.

8.         Indemnification and Contribution .

(a)    The Company will indemnify and hold harmless each Underwriter, its directors, officers, employees, affiliates and each person, if any, who controls such Underwriter within the meaning of Section 15 of the Act, against any losses, claims, damages or liabilities, joint or several, to which such Underwriter may become subject, under the Act or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or are based upon any untrue statement or alleged untrue statement of any material fact contained in any Registration Statement, any Preliminary Prospectus, the Prospectus, the Disclosure Package, any Issuer Free Writing Prospectus or any amendment or supplement thereto or arise out of or are based upon the omission or alleged omission to state therein a material fact required to be stated therein or necessary to make the statements therein not misleading, and will reimburse each Underwriter for any legal or other expenses as reasonably incurred by such Underwriter in connection with investigating or defending any such loss, claim, damage, liability or action as such expenses are incurred; provided, however , that the Company will not be liable under this Section 8(a) in any such case to the extent that any such loss, claim, damage or liability arises out of or is based upon an untrue statement or alleged untrue statement in or omission or alleged omission from any of such documents in reliance upon and in conformity with written information furnished to the Company by any Underwriter through the Representatives specifically for use therein, it being understood and agreed that the only such information consists of the information described as such in subsection (b) below.

(b)    Each Underwriter severally, but not jointly, will indemnify and hold harmless the Company, its directors and each person, if any, who controls the Company within the meaning of Section 15 of the Act, against any losses, claims, damages or liabilities to which the Company may become subject, under the Act or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof) arise out of or are based upon any untrue statement or alleged untrue statement of any material fact contained in any Registration Statement, any Preliminary Prospectus, the Prospectus, the Disclosure Package, any Issuer Free Writing Prospectus or any amendment or supplement thereto or arise out of or are based upon

16




the omission or the alleged omission to state therein a material fact required to be stated therein or necessary to make the statements therein not misleading, in each case to the extent, but only to the extent, that such untrue statement or alleged untrue statement or omission or alleged omission was made in reliance upon and in conformity with written information furnished to the Company by such Underwriter through the Representatives specifically for use therein, and will reimburse any legal or other expenses reasonably incurred by the Company in connection with investigating or defending any such loss, claim, damage, liability or action as such expenses are incurred, it being understood and agreed that the only such information furnished by any Underwriter consists of the following information: (i) the names of the Underwriters set forth on the front cover page of the most recent Preliminary Prospectus and the Prospectus, (ii) the names of the Underwriters set forth in the table of Underwriters under the first paragraph of text under the heading ‘‘Underwriting’’ in the most recent Preliminary Prospectus and the Prospectus, and (iii) the information contained in the third paragraph and the third sentence of the seventh paragraph under the caption ‘‘Underwriting’’ in the most recent Preliminary Prospectus and the Prospectus.

(c)    Promptly after receipt by an indemnified party under this Section 8 of notice of the commencement of any action, such indemnified party will, if a claim in respect thereof is to be made against an indemnifying party under such subsection, notify the indemnifying party of the commencement thereof; provided, however, that the failure to so notify the indemnifying party shall not relieve it from any liability which it may have under Section 8(a) or 8(b) except to the extent that it has been materially prejudiced (through the forfeiture of substantive rights or defenses) by such failure; and provided further that the failure to notify the indemnifying party shall not relieve it from any liability that it may have to an indemnified party otherwise than under this Section 8. If any such action is be brought against any indemnified party, and it notifies an indemnifying party of the commencement thereof, the indemnifying party will be entitled to participate therein and, to the extent that may wish, jointly with any other indemnifying party similarly notified, to assume the defense thereof, with counsel satisfactory to such indemnified party (who shall not, except with the consent of the indemnified party, be counsel to the indemnifying party), and after notice from the indemnifying party to the indemnified party of its election so to assume the defense thereof, the indemnifying party will not be liable to such indemnified party under Section 8(a) or 8(b) above, as the case may be, for any legal or other expenses subsequently incurred by such indemnified party in connection with the defense thereof other than reasonable costs of investigation. No indemnifying party shall, without the prior written consent of the indemnified party, effect any settlement of any pending or threatened action in respect of which any indemnified party is or could have been a party and indemnity could have been sought hereunder by such indemnified party unless such settlement (i) includes an unconditional release of such indemnified party from all liability on any claims that are the subject matter of such action and (ii) does not include a statement as to, or an admission of, fault, culpability or a failure to act by or on behalf of an indemnified party. No indemnifying party shall be liable for any settlement of any proceeding without its prior written consent, which consent shall not be unreasonably withheld. Notwithstanding the foregoing sentence, if at any time an indemnified party shall have requested that an indemnifying party reimburse the indemnified party for fees and expenses of counsel as contemplated by this paragraph, the indemnifying party shall be liable for any settlement of any proceeding effected without its written consent if (i) such settlement is entered into more than 30 days after receipt by the indemnifying party of such request and (ii) the indemnifying party shall not have reimbursed the indemnified party in accordance with such request prior to the date of such settlement.

(d)    If the indemnification provided for in this Section 8 is unavailable or insufficient to hold harmless an indemnified party under Section 8(a) or 8(b) above, then each indemnifying party shall, in lieu of indemnifying such indemnified party, contribute to the amount paid or payable by such indemnified party as a result of the losses, claims, damages or liabilities referred to in Section 8(a) or 8(b) above (i) in such proportion as is appropriate to reflect the relative benefits received by the Company on the one hand and the Underwriters on the other from the offering of the Securities or (ii) if the allocation provided by clause (i) above is not permitted by applicable law, in such proportion as is appropriate to reflect not only the relative benefits referred to in clause (i) above but also the relative fault of the Company on the one hand and the Underwriters on the other in connection with the statements or omissions that resulted in such losses, claims, damages or liabilities as well as any other relevant equitable

17




considerations. The relative benefits received by the Company on the one hand and the Underwriters on the other shall be deemed to be in the same proportion as the total net proceeds from the offering of the Securities (before deducting expenses) received by the Company bear to the total underwriting discounts and commissions received by the Underwriters, in each case as set forth in the table on the cover page of the Prospectus. Relative fault will be determined by reference to, among other things, whether the untrue or alleged untrue statement of a material fact or the omission or alleged omission to state a material fact relates to information supplied by the Company or the Underwriters and the parties’ relative intent, knowledge, access to information and opportunity to correct or prevent such untrue statement or omission. The Company and the Underwriters agree that it would not be just and equitable if contributions pursuant to this Section 8(d) were to be determined by pro rata allocation (even if the Underwriters were treated as one entity for such purpose) or by any other method of allocation that does not take into account the equitable considerations referred to in the first sentence of this Section 8(d). The amount paid or payable by an indemnified party as a result of the losses, claims, damages or liabilities referred to in the first sentence of this Section 8(d) shall be deemed to include any legal or other expenses reasonably incurred by such indemnified party in connection with investigating or defending against any action or claim which is the subject of this Section 8(d). Notwithstanding the provisions of this Section 8(d), no Underwriter shall be required to contribute any amount in excess of the amount by which the total price at which the Securities underwritten by it and distributed to the public were offered to the public exceeds the amount of any damages that such Underwriter has otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged omission. No person guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of the Act) shall be entitled to contribution from any person who was not guilty of such fraudulent misrepresentation. The Underwriters’ obligations in this subsection (d) to contribute are several in proportion to their respective underwriting obligations and not joint.

(e)    The obligations of the Company under this Section 8 shall be in addition to any liability that the Company may otherwise have, and shall extend, upon the same terms and conditions set forth in this Section 8, to the respective officers and directors of the Underwriters and each person, if any, who controls any Underwriter within the meaning of the Act; and the obligations of the Underwriters under this Section 8 shall be in addition to any liability that the respective Underwriters may otherwise have, and shall extend, upon the same terms and conditions, to each director of the Company, to each officer of the Company who has signed a Registration Statement and to each person, if any, who controls the Company within the meaning of the Act.

9.         Increase in Underwriters’ Commitments.     If any Underwriter or Underwriters default in their obligations to purchase Securities hereunder on the Closing Date (otherwise than for a failure of a condition set forth in Section 7 hereof or a reason sufficient to justify the termination of this Agreement under the provisions of Section 7(c)), and the aggregate number of shares of Securities that such defaulting Underwriter or Underwriters agreed but failed to purchase does not exceed 10% of the total number of shares of Securities that the Underwriters are obligated to purchase on the Closing Date, the Representatives may make arrangements satisfactory to the Company for the purchase of such Securities by other persons, including any of the Underwriters, but if no such arrangements are made by the Closing Date, the non-defaulting Underwriters shall be obligated severally, in proportion to their respective commitments hereunder, to purchase the Securities that such defaulting Underwriters agreed but failed to purchase on the Closing Date. If any Underwriter or Underwriters so default and the aggregate number of shares of Securities with respect to which such default or defaults occur exceeds 10% of the total number of shares of Securities that the Underwriters are obligated to purchase on the Closing Date and arrangements satisfactory to the Representatives and the Company for the purchase of such Securities by other persons are not made within 36 hours after such default, the Company shall be entitled to a further period of 36 hours to make arrangements satisfactory to the Representatives for the purchase of such Securities. In the event that, within the respective prescribed period, the Representatives notify the Company that they have arranged for the purchase of such defaulted Securities, or the Company notifies the Representatives that it has arranged for the purchase of such defaulted Securities, the Representatives or the Company shall have the right to postpone the Closing Date for a period of not more than seven days, in order to effect whatever changes may thereby be made necessary in the Registration Statement,

18




the Disclosure Package or the Prospectus, or in any other documents or arrangements. If, after giving effect to any arrangements for the purchase of the defaulted Securities by the Representatives and the Company as provided above, the aggregate principal amount of Securities which remain unpurchased exceeds 10% of the total number of shares of Securities that the Underwriters are obligated to purchase on the Closing date, then this Agreement will terminate without liability on the part of any non-defaulting Underwriter or the Company, except as provided in Section 10. As used in this Agreement, the term ‘‘Underwriter’’ includes any person substituted for an Underwriter under this Section. Nothing herein will relieve a defaulting Underwriter from liability for its default.

10.         Survival of Certain Representations and Obligations.     The respective indemnities, agreements, representations, warranties and other statements of the Company or its officers and of the several Underwriters set forth in or made pursuant to this Agreement will remain in full force and effect, regardless of any investigation, or statement as to the results thereof, made by or on behalf of any Underwriter, the Company or any of their respective representatives, officers or directors or any controlling person, and will survive delivery of and payment for the Securities. If for any reason the purchase of the Securities by the Underwriters is not consummated, the Company shall remain responsible for the expenses to be paid or reimbursed by it pursuant to Section 5 and the respective obligations of the Company and the Underwriter pursuant to Section 8 shall remain in effect, and, if any Securities have been purchased hereunder, the representations and warranties in Section 2 and all obligations under Section 5 shall also remain in effect. If the purchase of the Securities by the Underwriter is not consummated for any reason other than solely because of the occurrence of any event specified in clause (iv), (v), (vii), (viii) or (ix) of Section 7(d), the Company will reimburse the Underwriters for all out-of-pocket expenses (including fees and disbursements of counsel) reasonably incurred by them in connection with the offering of the Securities.

11.         Notices.     All communications hereunder will be in writing and, if sent to the Underwriters, will be mailed, delivered or e-mailed and confirmed to the Representatives, Lehman Brothers Inc., 745 Seventh Avenue, New York, NY 10019, Attn: Debt Capital Markets — Financial Institutions Group, Fax: 212-526-0943 (with a copy to the General Counsel at the same address) and UBS Securities LLC, 677 Washington Boulevard, Stamford, CT 06901, Attn: Syndicate Department, Fax: 203-719-0495 (with a copy to the Legal Department at the same address); or, if sent to the Company, will be mailed, delivered or e-mailed and confirmed to it at the address set forth in the Registration Statement, Attention: Secretary; provided , however , that any notice to an Underwriter pursuant to Section 8 will be mailed, delivered or e-mailed and confirmed to such Underwriter.

12.         No Fiduciary Duty.     The Company acknowledges and agrees that in connection with this offering, sale of the Securities or any other services the Underwriters may be deemed to be providing hereunder, notwithstanding any preexisting relationship, advisory or otherwise, between the parties or any oral representations or assurances previously or subsequently made by the Underwriters: (i) no fiduciary or agency relationship between the Company and any other person, on the one hand, and the several Underwriters, on the other, exists; (ii) the several Underwriters are not acting as advisors, expert or otherwise, to the Company, including, without limitation, with respect to the determination of the public offering price of the Preference Shares, and such relationship between the Company, on the one hand, and the several Underwriters, on the other, is entirely and solely commercial, based on arms-length negotiations; (iii) any duties and obligations that the several Underwriters may have to the Company shall be limited to those duties and obligations specifically stated herein; and (iv) the several Underwriters and their respective affiliates may have interests that differ from those of the Company. The Company hereby waives any claims that the Company may have against the Underwriters with respect to any breach of fiduciary duty in connection with the offering.

13.         Research Analyst Independence.     The Company acknowledges that the Underwriters’ research analysts and research departments are required to be independent from their respective investment banking divisions and are subject to certain regulations and internal policies, and that such Underwriters’ research analysts may hold views and make statements or investment recommendations and/or publish research reports with respect to the Company and/or the offering of the Securities that differ from the views of their respective investment banking divisions. The Company hereby waives and releases, to the fullest extent permitted by law, any claims that the Company may have against the

19




Underwriters with respect to any conflict of interest that may arise from the fact that the views expressed by their independent research analysts and research departments may be different from or inconsistent with the views or advice communicated to the Company by such Underwriters’ investment banking divisions. The Company acknowledges that each of the Underwriters is a full service securities firm and as such from time to time, subject to applicable securities laws, may effect transactions for its own account or the account of its customers and hold long or short positions in debt or equity securities of the companies that may be the subject of the transactions contemplated by this Agreement.

14.         Successors.     This Agreement will inure to the benefit of and be binding upon the parties hereto and their respective personal representatives (in the case of a natural person) and successors and the officers and directors and controlling persons referred to in Section 8, and no other person will have any right or obligation hereunder.

15.         Counterparts.     This Agreement may be executed in any number of counterparts, each of which shall be deemed to be an original, but all such counterparts shall together constitute one and the same Agreement.

16.         Applicable Law .     This Agreement shall be governed by, and construed in accordance with, the laws of the State of New York, without regard to principles of conflicts of laws.

The Company irrevocably (i) agrees that any legal suit, action or proceeding against the Company arising out of or based upon this Agreement or the transactions contemplated hereby may be instituted in any state or federal court located in the Borough of Manhattan, The City of New York, New York (each a ‘‘ New York Court ’’), (ii) waives, to the fullest extent it may effectively do so, any objection which it may now or hereafter have to the laying of venue of any such proceeding and (iii) submits to the non-exclusive jurisdiction of such New York Court in any such suit, action or proceeding. The Company has appointed CT Corporation, New York, New York, as its authorized agent (the ‘‘ Company’s Authorized Agent ’’) upon whom process may be served in any such action arising out of or based on this Agreement or the transactions contemplated hereby which may be instituted in any New York Court, expressly consents to the jurisdiction of any such court in respect of any such action, and waives any other requirements of or objections to personal jurisdiction with respect thereto. Such appointment shall be irrevocable. The Company represents and warrants that the Company’s Authorized Agent has agreed to act as such agent for service of process and agrees to take any and all action, including the filing of any and all documents and instruments, that may be necessary to continue such appointment in full force and effect as aforesaid. Service of process upon the Company’s Authorized Agent and written notice of such service to the Company shall be deemed, in every respect, effective service of process upon the Company.

In respect of any judgment or order given or made for any amount due hereunder that is expressed and paid in a currency (the ‘‘ judgment currency ’’) other than United States dollars, the party against whom such judgment or order has been given or made will indemnify each party in whose favor such judgment or order has been given or made (the ‘‘ Indemnitee ’’) against any loss incurred by the Indemnitee as a result of any variation as between (i) the rate of exchange at which the United States dollar amount is converted into the judgment currency for the purpose of such judgment or order and (ii) the rate of exchange at which the Indemnitee is able to purchase United States dollars with the amount of judgment currency actually received by the Indemnitee. The foregoing indemnity shall constitute a separate and independent obligation of each of the Company and the Underwriters and shall continue in full force and effect notwithstanding any such judgment or order as aforesaid. The term ‘‘ rate of exchange ’’ shall include any premiums and costs of exchange payable in connection with the purchase of or conversion into United States dollars.

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If the foregoing is in accordance with the Representatives’ understanding of our agreement, kindly sign and return to the Company one of the counterparts hereof, whereupon it will become a binding agreement among the Company and the Underwriters in accordance with its terms.


  Very truly yours,
    
ASPEN INSURANCE HOLDINGS LIMITED
     
  By /s/ Julian Cusack                        
    Name: Julian Cusack
    Title: Chief Financial Officer

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The foregoing Underwriting Agreement is hereby
confirmed and accepted as of the date first above written.

LEHMAN BROTHERS INC.  

By / s/ Martin Goldberg
         Authorized Representative

UBS SECURITIES LLC

By: / s/ Scott Yeager
         Authorized Representative

By: /s/ Demetrios Tsapralis
         Authorized Representative

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SCHEDULE 1


Underwriter Number of Preference
Shares
Lehman Brothers Inc. . 2,800,000
UBS Securities LLC . 2,800,000
Deutsche Bank Securities Inc. . 1,000,000
Goldman, Sachs & Co. . 1,000,000
Dowling & Partners Securities, LLC. 400,000
Total 8,000,000

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SCHEDULE 2

•  Final Term Sheet, dated November 10, 2006, relating to the Securities, as filed pursuant to Rule 433 under the Act and attached as Schedule 3 hereto.

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SCHEDULE 3

Filed Pursuant to Rule 433
Registration Statement No. 333-129214

 ASPEN INSURANCE HOLDINGS LIMITED 

 PERPETUAL NON-CUMULATIVE PREFERENCE SHARES 

Final Term Sheet

Issuer: Aspen Insurance Holdings Limited, a Bermudian holding company
Security Type: 7.401% Perpetual Non-Cumulative Preference Shares (the ‘‘Preference Shares’’)
Amount: $200,000,000 (8,000,000 shares)
Expected Ratings: Ba1 (Moody’s)/BBB− (S&P)
Legal Format: SEC Registered
Trade Date: November 10, 2006
Settlement Date (T+ 3): November 15, 2006
Issue Price: $25 per share
Maturity: Perpetual
Liquidation Preference: $25 per share
Dividend Rate During Fixed Rate Period: 7.401% of the $25 liquidation preference of each share from Settlement Date up to but excluding the January 1, 2017 Dividend Payment Date, payable on a non-cumulative basis
Dividend Rate During Floating Rate Period: Commencing on January 1, 2017, dividends will be payable on a non-cumulative basis at a floating annual rate, reset quarterly, equal to 3-month LIBOR plus 3.28%
First Dividend Payment Date: January 1, 2007
Dividend Payment Dates: January 1, April 1, July 1 and October 1
Optional Redemption: On or after January 1, 2017, in whole or in part, at $25 per share, plus declared and unpaid dividends.
At any time prior to January 1, 2017, in whole but not in part, upon a proposal for merger, amalgamation, or consolidation, arrangement, reconstruction or discontinuance or a proposal for any other matter that requires as a result of a change of

25




Bermuda law an affirmative vote of the holders of the Preference Shares, at a redemption price equal to the greater of: (1) $25 per share and (2) the sum of the present value of $25 per share and the present value of all undeclared dividends for the dividend periods from the redemption date to and including the January 1, 2017 Dividend Payment Date, in each case, discounted to the redemption date on a quarterly basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate, plus 45 basis points, and in the case of both (1) and (2) plus declared and unpaid dividends.
Latest Termination Date of Replacement Capital Covenant: November 15, 2046
CUSIP/ISIN: G05384 13 9/BMG053841398
Listing: The Company has applied to have the Preference Shares listed on the NYSE under the symbol ‘‘AHLPRA’’
Underwriting Discounts and Commissions: $0.3375 per share
Maximum Selling Concession Per Share: $0.20 per share
Reallowance to Other Dealers: $0.15 per share
Estimated Net Proceeds to Company, After Underwriting Discounts and Commissions and Estimated Expenses: Approximately $196.8 million
Joint Book-Running Managers: Lehman Brothers Inc. (2,800,000 shares) (35.0%)
UBS Securities LLC (2,800,000 shares) (35.0%)
Co-Managers: Deutsche Bank Securities Inc. (1,000,000 shares) (12.5%)
Goldman, Sachs & Co. (1,000,000 shares) (12.5%)
Dowling & Partners Securities, LLC (400,000 shares)    (5.0%)
Additional Disclosure: As disclosed in a Current Report on Form 8-K filed by the Company on November 9, 2006, the Company advises that the amount disclosed in its Annual Report on Form 10-K for the year ended December 31, 2005 in respect of the maximum amount of distributions that the Company’s insurance subsidiaries, Aspen Insurance UK Limited, Aspen Insurance Limited and Aspen Specialty Insurance Company, could have paid to the Company under applicable laws and regulations without prior regulatory approval should have been approximately $86.5 million and was overstated by approximately $64.6 million. The Company further advises that such amount as at September 30, 2006 was approximately $205.0 million.

The issuer has filed a registration statement (including a prospectus) with the U.S. Securities and Exchange Commission (the ‘‘SEC’’) for the offering to which this communication relates. Before you

26




invest, you should read the prospectus for this offering in that registration statement and other documents the issuer has filed with the SEC for more complete information about the issuer and this offering. You may get these documents for free by visiting EDGAR on the SEC Web site at www.sec.gov . Alternatively, the issuer, any underwriter or any dealer participating in this offering will arrange to send you the prospectus if you request it by calling toll-free Lehman Brothers Inc. at 1-888-603-5847 and UBS Securities LLC at 1-888-722-9555, extension 1088.

Terms are used in this term sheet with the meanings assigned to them in the preliminary prospectus, dated November 8, 2006, included in the registration statement referred to above.

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ANNEX I-A

[Form of Opinion of LeBoeuf, Lamb, Greene & MacRae LLP,
special United States counsel for the Company]

28




ANNEX I-B

[Form of Negative Assurance Letter of LeBoeuf, Lamb, Greene & MacRae LLP,
special United States counsel for the Company]

29




ANNEX II

[Form of Opinion of Appleby Spurling Hunter, Bermuda counsel for the Company]

30




ANNEX III

[Form of Opinion of LeBoeuf, Lamb, Greene & MacRae LLP,
U.K. counsel for the Company]

31




ANNEX IV

[Form of Opinion of David Curtin, General Counsel to the Company]

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Exhibit 4.1

EXECUTION COPY

CERTIFICATE OF DESIGNATION

OF

PERPETUAL NON-CUMULATIVE PREFERENCE SHARES

OF

ASPEN INSURANCE HOLDINGS LIMITED

ASPEN INSURANCE HOLDINGS LIMITED, a Bermudian company (the ‘‘ Company ’’), hereby certifies that pursuant to resolutions of the Board of Directors of the Company duly adopted on October 17, 2005 and October 30, 2006 and of the Pricing Committee of the Board of Directors duly adopted on November 10, 2006, the creation and issue of 8,000,000 7.401% Perpetual Non-Cumulative Preference Shares, par value 0.15144558¢ per share (the ‘‘ Preference Shares ’’), was authorized and the designation, rights, preferences, privileges and qualifications, limitations and restrictions of the 8,000,000 Preference Shares (in addition to the applicable provisions set forth in the Company’s Memorandum of Association (the ‘‘ Memorandum of Association ’’) and Amended and Restated Bye-Laws (the ‘‘ Bye-Laws ’’)), were fixed as follows:

1.     Designation .

The designation of this series of preference shares shall be the ‘‘7.401% Perpetual Non-Cumulative Preference Shares’’, and the number of shares constituting this series shall be 8,000,000; provided that , if the Company elects to issue additional Preference Shares after the date of this Certificate of Designation, as contemplated in the prospectus supplement dated November 10, 2006 that relates to the Preference Shares, the Company may increase the number of shares constituting this series by the number of such additional Preference Shares. The Preference Shares shall have a liquidation preference (the ‘‘ liquidation preference ’’) of U.S.$25 per Preference Share. Each Preference Share shall be identical in all respects to every other Preference Share, except for the issue price, date of issuance, and, in some cases, the initial dividend payment date. Any Preference Shares issued after the date of this Certificate of Designation shall be issued on a Dividend Payment Date (as defined below) at an issue price that does not exceed the liquidation preference of U.S.$25 per Preference Share. The number of authorized Preference Shares may be reduced (but not below the number of Preference Shares then issued and outstanding) by further resolution duly adopted by the Board of Directors. No such reduction shall affect the due authorization of any issued and outstanding Preference Shares of this series.

2.     Definitions. As used herein, the following terms shall have the following meanings:

‘‘ Affiliate ’’ has the meaning ascribed to it, on the date hereof, under Rule 405 of the Securities Act of 1933, as amended.

‘‘ Agent Members ’’ has the meaning assigned to such term in Section 13.

‘‘ Appointing Preference Shares ’’ mean any other class or series of preference shares of the Company, including any Perpetual PIERS and the Perpetual Preference Shares issued upon conversion of the Perpetual PIERS, if any, ranking equally with the Preference Shares either as to dividend rights or rights upon liquidation, winding-up or dissolution and upon which like appointing rights have been conferred and are exercisable.

‘‘ Appointing Rights ’’ have the meaning assigned to such term in Section 5(c).

‘‘ Board of Directors ’’ means the Board of Directors of the Company or, with respect to any action to be taken by the Board of Directors, any committee of the Board of Directors duly authorized to take such action.

1




‘‘ Business Day ’’ means a day that is a Monday, Tuesday, Wednesday, Thursday or Friday and is not a day on which banking institutions in New York City or Bermuda generally are authorized or obligated by law or executive order to close.

‘‘ Calculation Agent ’’ means the nationally recognized calculation agent appointed by the Company prior to any redemption notice and prior to January 1, 2017.

‘‘ Capital Stock ’’ of any Person means any and all shares, interests, rights to purchase, warrants, options, participations or other equivalents of or interests in (however designated) equity of such Person, including any Preferred Stock, but excluding any debt securities convertible into such equity.

‘‘ Comparable Treasury Issue ’’ means the United States Treasury security selected by the Calculation Agent as having a maturity comparable to the term remaining to the Dividend Payment Date on January 1, 2017 that would be utilized, at the time of selection and in accordance with customary financial practice, in pricing new issues of corporate perpetual preferred stock having similar terms as the Preference Shares with respect to the payment of dividends and distributions of assets upon liquidation, dissolution or winding-up of the issuer of such preferred stock.

‘‘ Comparable Treasury Price ’’ means, with respect to any Redemption Date for the Preference Shares, the average of the Reference Treasury Dealer Quotations for such Redemption Date, after excluding the highest and lowest of such Reference Treasury Dealer Quotations, or if the Calculation Agent obtains fewer than five such Reference Treasury Dealer Quotations, the average of all such quotations.

‘‘ Depositary ’’ means, with respect to Preference Shares issuable in whole or in part in the form of one or more Global Preference Shares, a clearing agency registered under Section 17A of the Exchange Act that is designated to act as depositary for such Preference Shares, and initially shall be DTC.

‘‘ Dividend Payment Date ’’ has the meaning assigned to such term in Section 4(a).

‘‘ Dividend Period ’’ has the meaning assigned to such term in Section 4(d).

‘‘ Dividend Record Date ’’ means, with respect to each Dividend Payment Date, 5:00 p.m. (New York City time) on the December 15, March 15, June 15 or September 15 immediately preceding such Dividend Payment Date.

‘‘ DTC ’’ means The Depository Trust Company.

‘‘ Exchange Act ’’ means the United States Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder.

‘‘ Fixed Rate ’’ means an amount per annum equal to 7.401% of the liquidation preference per Preference Share.

‘‘ Fixed Rate Period ’’ means the Dividend Periods up to but excluding January 1, 2017, in which dividends on the Preference Shares shall be payable at the Fixed Rate.

‘‘ Floating Rate ’’ means an amount per annum equal to 3-Month LIBOR plus 3.28%; provided that the Floating Rate will in no event exceed the maximum rate permitted by law. The Floating Rate shall be reset on the applicable LIBOR Reset Date for each Dividend Period during the Floating Rate Period.

‘‘ Floating Rate Period ’’ means each Dividend Period commencing after the expiration of the Fixed Rate Period, in which dividends on the Preference Shares shall be payable at the Floating Rate.

‘‘ Global Preference Shares ’’ has the meaning assigned to such term in Section 13(a).

‘‘ Holder ’’ or ‘‘ holder ’’ means the Person in whose name a Preference Share is registered on the Registrar’s books.

‘‘ Issue Date ’’ means November 15, 2006, the original date of issuance of the Preference Shares.

‘‘ Junior Shares ’’ mean the Ordinary Shares and any other class of share capital or series of preference shares established after the Issue Date by the Board of Directors, the terms of which do not expressly provide that such class or series ranks senior to or on a parity with, the Preference Shares as to dividend rights or rights upon the liquidation, winding-up or dissolution of the Company.

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‘‘ LIBOR Determination Date ’’ means the second London Banking Day immediately preceding the applicable LIBOR Reset Date.

‘‘ LIBOR Reset Date ’’ has the meaning assigned to such term in Section 4(c).

‘‘ Liquidation Distribution ’’ has the meaning assigned to such term in Section 7(a).

‘‘ liquidation preference ’’ has the meaning assigned to such term in Section 1.

‘‘ London Banking Day ’’ means a day on which commercial banks are open for business, including dealings in United States dollars, in London.

‘‘ Moneyline Telerate Page 3750 ’’ means the display page on Moneyline Telerate (or any successor service) on such page (or any other page as may replace such page on such service) for the purpose of displaying the London interbank rates of major banks for United States dollars.

‘‘ Nonpayment ’’ has the meaning assigned to such term in Section 5(c).

‘‘ NYSE ’’ means the New York Stock Exchange, Inc.

‘‘ Officer ’’ means the Chief Executive Officer, the Chief Financial Officer, the Chief Operating Officer, the Secretary and the Assistant Secretary of the Company.

‘‘ Ordinary Shares ’’ mean the ordinary shares, par value 0.15144558¢ per share, of the Company, or any other class of shares resulting from successive changes or reclassifications of such Ordinary Shares consisting solely of changes in par value, or from par value to no par value, or as a result of a subdivision, combination, merger, consolidation or similar transaction in which the Company is a constituent corporation.

‘‘ Parity Shares ’’ mean the Preference Shares, the Perpetual PIERS and any Perpetual Preference Shares issued upon conversion of Perpetual PIERS, and any other class of share capital or series of preference shares established after the Issue Date by the Board of Directors, the terms of which expressly provide that such class or series will rank on a parity with the Preference Shares as to dividend rights or rights upon the liquidation, winding-up or dissolution of the Company.

‘‘ Paying Agent ’’ initially means Mellon Investors Services LLC. The Company may, in its sole discretion, remove the Paying Agent within 10 calendar days’ prior notice to the Paying Agent, provided that the Company shall appoint a successor Paying Agent who shall accept such appointment prior to the effectiveness of such removal.

‘‘ Perpetual PIERS ’’ mean the series of preference shares, par value 0.15144558¢ per share, of the Company designated as the 5.625% Perpetual Preferred Income Equity Replacement Securities (Perpetual PIERS).

‘‘ Perpetual Preference Shares ’’ mean the series of preference shares, par value 0.15144558¢ per share, of the Company designated as the Perpetual Preference Shares, issuable upon the conversion of the Perpetual PIERS.

‘‘ Person ’’ means any individual, corporation, general partnership, limited partnership, limited liability partnership, joint venture, association, joint-stock company, trust, limited liability company, unincorporated organization or government or any agency or political subdivision thereof.

‘‘ Preference Share Director ’’ has the meaning assigned to such term in Section 5(c).

‘‘ Preferred Stock ,’’ as applied to the Capital Stock of any Person, means Capital Stock of any class of classes (however designated) that is preferred as the payment of dividends, or as to distribution of assets upon any voluntary or involuntary liquidation or dissolution of such Person over other shares of Capital Stock or any other class of such Person.

‘‘ Redemption Date ’’ means, in the case of an optional redemption, the day specified in the Company’s notice of redemption.

‘‘ Reference Treasury Dealer ’’ means each of three primary U.S. government securities dealers (each a ‘‘Primary Treasury Dealer’’), as specified by the Company; provided that if any Primary Treasury Dealer

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as specified by the Company ceases to be a Primary Treasury Dealer, the Company shall substitute for such Primary Treasury Dealer another Primary Treasury Dealer and if the Company fails to select a substitute within a reasonable period of time, then the substitute will be a Primary Treasury Dealer selected by the Calculation Agent after consultation with the Company.

‘‘ Reference Treasury Dealer Quotations ’’ means, with respect to the Reference Treasury Dealer and any Redemption Date, the average, as determined by the Calculation Agent, of the bid and asked prices for the Comparable Treasury Issue (expressed, in each case, as a percentage of its principal amount) quoted in writing to the Calculation Agent by such Reference Treasury Dealer at 5:00 p.m. (New York City time) on the third Business Day preceding such Redemption Date.

‘‘ Register ’’ means the register of issued Preference Shares maintained by the Registrar.

‘‘ Registrar ’’ initially means Mellon Investors Services LLC. The Company may, in its sole discretion, remove the Registrar within 10 calendar days’ prior notice to the Registrar, provided that the Company shall appoint a successor Registrar who shall accept such appointment prior to the effectiveness of such removal.

‘‘ Securities Act ’’ means the United States Securities Act of 1933, as amended.

‘‘ Senior Shares ’’ mean any class of share capital or series of preference shares established after the Issue Date by the Board of Directors, the terms of which expressly provide that such class or series will rank senior to the Preference Shares as to dividend rights or rights upon the liquidation, winding-up or dissolution of the Company.

‘‘ 3-Month LIBOR ’’ means, with respect to any LIBOR Determination Date:

(i)  the rate for 3-month deposits in United States dollars as that appears on the Moneyline Telerate Page 3750 as of 11:00 a.m. (London time) on the LIBOR Determination Date for that Floating Rate Period, unless fewer than two such offered rates so appear;
(ii)  if fewer than two offered rates appear, or no rate appears, as the case may be, on the LIBOR Determination Date for that Floating Date Period on the Moneyline Telerate Page 3750, the rate calculated by the Calculation Agent based on two offered quotations after requesting the principal London offices of each of four major reference banks in the London interbank market to provide the Calculation Agent with offered quotations for deposits in United States dollars for the period of three months, commencing on the first day of that Floating Rate Period, to prime banks in the London interbank markets at approximately 11:00 a.m. (London time) on that date and in a principal amount that is representative for a single transaction in United States dollars in that market at that time;
(iii)  if fewer than two offered quotations referred to in clause (ii) are provided as requested, the rate calculated by the Calculation Agent as the arithmetic mean of the rates quoted at approximately 11:00 a.m. (New York City time) on the LIBOR Determination Date for that Floating Rate Period by three major banks (which will not include affiliates of the Company) in New York City selected by the Calculation Agent for loans in United States dollars to leading European banks for a period of three months and in a principal amount that is representative for a single transaction in United States dollars in that market at that time; or
(iv)  if the banks so selected by the Calculation Agent are not quoting as mentioned in clause (iii), the rate equal to the 3-Month LIBOR for the previous Floating Rate Period.

‘‘ Transfer Agent ’’ initially means Mellon Investors Services LLC. The Company may, in its sole discretion, remove the Transfer Agent with 10 days’ prior notice to the Transfer Agent; provided , that the Company shall appoint a successor Transfer Agent who shall accept such appointment prior to the effectiveness of such removal.

‘‘ Treasury Rate ’’ means the rate per year equal to the quarterly equivalent yield to maturity of the Comparable Treasury Issue, calculated using a price for the Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the Comparable Treasury Price for such Redemption Date. The Treasury Rate shall be calculated on the third Business Day preceding the Redemption Date.

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3.     Ranking. The Preference Shares shall, with respect to dividend rights or rights upon the liquidation, winding-up or dissolution of the Company, rank (a) senior to all Junior Shares, including, without limitation, the Ordinary Shares, (b) on a parity with all Parity Shares, including, without limitation, the Perpetual PIERS and the Perpetual Preference Shares issuable upon conversion of the Perpetual PIERS, (c) junior to any Senior Shares and (d) junior to all of the Company’s existing and future debt obligations.

4.     Dividend Rights .

(a)    The holders of outstanding Preference Shares shall be entitled to receive dividends, when, as and if declared by the Board of Directors, out of funds legally available for that purpose under Bermuda law and to the extent that at the time of declaration and payment the Company has reasonable grounds to believe that it is, and after the payment would be, able to pay its liabilities as they become due and if the realizable value of its assets would thereby not be less than the aggregate of its liabilities and issued share capital and share capital premium accounts, at the Fixed Rate, as described in Section 4(b), from the Issue Date, quarterly in arrears, on January 1, April 1, July 1 and October 1 of each year (each, a ‘‘ Dividend Payment Date ’’), commencing on January 1, 2007, and thereafter at the Floating Rate, as described in Section 4(c), quarterly in arrears on each Dividend Payment Date, commencing on January 1, 2017.

(b)    During the Fixed Rate Period, when, as and if declared by the Board of Directors, out of funds legally available for the payment of dividends under Bermuda law, dividends on the Preference Shares shall be payable quarterly at the Fixed Rate on a non-cumulative basis with respect to each Dividend Period.

(c)    During each Floating Rate Period, when, as and if declared by the Board of Directors, out of funds legally available for the payment of dividends under Bermuda law, dividends on the Preference Shares shall be payable quarterly, with respect to each Floating Rate Period at the Floating Rate on the LIBOR Determination Date for the relevant Dividend Period on a non-cumulative basis on each Dividend Payment Date. The Floating Rate shall be reset quarterly on January 1, April 1, July 1 and October 1 of each year (each, a ‘‘ LIBOR Reset Date ’’) for the Dividend Period beginning on such date. During the Floating Rate Period, if any LIBOR Reset Date falls on a day that is not a Business Day, the LIBOR Reset Date shall be postponed to the next day that is a Business Day.

(d)    A dividend period (each, a ‘‘ Dividend Period ’’) is the period from and including a Dividend Payment Date to, but excluding, the next Dividend Payment Date, except that the initial Dividend Period shall commence on and include the Issue Date of the Preference Shares and shall end on and exclude the January 1, 2007 Dividend Payment Date. During the Fixed Rate Period, if any Dividend Payment Date is not a Business Day, then dividends will be payable on the first Business Day following such Dividend Payment Date, without accrual to the actual payment date. During the Floating Rate Period, if any Dividend Payment Date other than a Redemption Date falls on a day that is not a Business Day, the Dividend Payment Date shall be postponed to the next day that is a Business Day, and dividends will accumulate to such actual Dividend Payment Date. If a Redemption Date, whether during the Fixed Rate Period or the Floating Rate Period, falls on a day that is not a Business Day, the payment of dividends and redemption price shall be made on the first Business Day following such Redemption Date, without accrual to the actual payment date.

(e)    During the Fixed Rate Period, dividends payable on the Preference Shares shall be computed on the basis of a 360-day year consisting of twelve 30-day months with respect to a full Dividend Period, and on the basis of the actual number of days elapsed during the period with respect to a Dividend Period other than a full Dividend Period.

(f)    During the Floating Rate Period, dividends payable on the Preference Shares shall be computed by multiplying the Floating Rate in effect for such Dividend Period by a fraction, the numerator of which shall be the actual number of days elapsed during such Dividend Period (determined by including the first day of such Dividend Period and excluding the last day, which is the Dividend Payment Date), and the denominator of which shall be 360, and multiplying the result by the aggregate liquidation preference of the Preference Shares.

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(g)    Dividends shall be paid to the holders of the Preference Shares on the applicable Dividend Record Date. The Dividend Record Date shall apply regardless of whether any particular Dividend Record Date is a Business Day.

(h)         Dividends on the Preference Shares shall not be cumulative. To the extent that any dividends payable on the Preference Shares on any Dividend Payment Date are not declared and paid, in full or otherwise, on such Dividend Payment Date, then such unpaid dividends shall not accumulate and the Company shall have no obligation to pay dividends for such Dividend Period on or subsequent to such Dividend Payment Date, whether or not dividends are declared on Preference Shares for any subsequent Dividend Period.

(i)    So long as any Preference Shares remain outstanding, unless the full dividends for the most recently ended Dividend Period on all outstanding Preference Shares and Parity Shares have been declared and paid (or declared and a sum sufficient for the payment thereof has been set aside): (i) no dividend whatsoever shall be declared or paid on the Junior Shares; and (ii) no Junior Shares shall be purchased, redeemed or otherwise acquired for consideration by the Company, directly or indirectly (other than as a result of a reclassification of Junior Shares for or into other Junior Shares, or the exchange or conversion of one share of Junior Shares for or into another share of Junior Shares). In such event, the restrictions set forth in the preceding sentence shall continue until such time as full dividends on all outstanding Preference Shares and Parity Shares have been declared and paid (or declared and a sum sufficient for the payment thereof has been set aside) for four consecutive Dividend Periods.

(j)    When dividends are not paid in full (or duly provided for) on any Dividend Payment Date (or, in the case of Parity Shares having dividend payment dates different from the Dividend Payment Dates, on a dividend payment date falling within a Dividend Period) upon the Preference Shares and any Parity Shares, all dividends declared upon the Preference Shares and all such Parity Shares payable on such Dividend Payment Date (or, in the case of Parity Shares having dividend payment dates different from the Dividend Payment Dates, on a dividend payment date falling within the Dividend Period related to such Dividend Payment Date) shall be declared pro rata based on the aggregate liquidation preference of the Preference Shares and such Parity Shares.

(k)    Holders of Preference Shares shall have the Appointing Rights provided in Section 5(c).

5.     Voting, Appointing and Other Rights.

(a)    The Preference Shares shall have no voting rights except as provided in Section 5(b) and Section 6 or otherwise required by Bermuda law from time to time.

(b)    Notwithstanding the Bye-Laws, so long as any Preference Shares remain outstanding, unless a greater percentage shall then be required by applicable law, the Company shall not, without the affirmative vote or written consent of the holders of at least 66 2/3% of the aggregate liquidation preference of the Preference Shares then outstanding and all series of Appointing Preference Shares then outstanding, voting or consenting, as the case may be, together as a single class:

(i)    authorize or issue any class or series of Senior Shares (or any security convertible into or exchangeable for Senior Shares); or

(ii)    amend the Memorandum of Associations or Bye-Laws in such a manner that would materially adversely affect the specified rights, preferences or privileges of holders of the Preference Shares.

For the avoidance of doubt, the Company may create, authorize, increase the authorized amount of, or issue any class or series of Parity Shares or Junior Shares, without the affirmative vote or written consent of the holders of the Preference Shares, and in taking such actions the Company shall not be deemed to have materially adversely affected the specified rights, preferences or privileges of the holders of the Preference Shares.

(c)    Whenever full dividends on any Preference Shares shall have not been declared and paid for the equivalent of any six Dividend Periods, whether or not consecutive (a ‘‘ Nonpayment ’’), the holders of the Preference Shares then outstanding and all series of Appointing Preference Shares then outstanding,

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acting together as a single class, will be entitled to the appointment (the ‘‘ Appointing Rights ’’) of a total of two additional members to the Board of Directors (each, a ‘‘ Preference Share Director ’’); provided that the appointment of any such directors shall not cause the Company to violate the corporate governance requirement of the NYSE as applied to United States issuers (or any other securities exchange or automated quotation system on which securities of the Company may be then listed or quoted) that listed companies must have a majority of independent directors. In the event of a Nonpayment, the number of members of the Board of Directors shall automatically increase by two, subject to the Bye-Laws. The Preference Share Directors shall be selected by the holders of at least a majority of the aggregate liquidation preference of the Preference Shares and any Appointing Preference Shares at a special meeting called at the request of the holders of at least 20% of the then outstanding aggregate liquidation preference of the Preference Shares and any series of Appointing Preference Shares then outstanding. Whether a majority of the Preference Shares and any Appointing Preference Shares have been affirmatively voted in favor of an appointment shall be determined by reference to the aggregate liquidation preference of the Preference Shares and any Appointing Preference Shares affirmatively voted at the meeting called to exercise the Appointing Rights.

If the holders of the Preference Shares become entitled to the appointment of Preference Share Directors to the Board of Directors, the Company shall promptly give notice to all holders and take all action necessary, including calling a meeting or circulating a consent to permit the nomination and selection of such directors.

The Board of Directors shall promptly duly appoint the Preference Share Directors selected by the holders of the Preference Shares and any series of Appointing Preference Shares then outstanding in accordance with this Section 5(c). The Board of Directors shall, subject to the Bye-Laws, determine which class or classes, as applicable, of directors the Preference Share Directors shall be a part of and shall allocate the Preference Share Directors to the class or classes, as applicable, having the longest terms of office remaining at the time of such appointment. Each Preference Share Director shall each be entitled to one vote per director on any matter. If, at the time the Appointing Rights are vested in the holders of the Preference Shares and any Appointing Preference Shares, there are not two vacancies on the Board of Directors, the Company will use its best efforts to increase the number of directors constituting the Board of Directors.

So long as a Nonpayment shall continue, any vacancy in the office of a Preference Share Director (other than prior to the initial appointment of Preference Share Directors after a Nonpayment) may be filled by the Board of Directors pursuant to an exercise of the Appointing Rights of the holders of at least a majority of the aggregate liquidation preference of the Preference Shares then outstanding and any other Appointing Preference Shares then outstanding, acting together as a single class.

When the term of a class of directors of which any Preference Share Director is a part is expiring, the Board of Directors shall set the size of such class of directors to be elected by the holders of the Ordinary Shares at a level to include such Preference Share Director duly appointed by the Board of Directors upon the exercise of the Appointing Rights.

If and when dividends for four consecutive Dividend Periods following a Nonpayment have been paid in full (or declared and a sum sufficient for the payment thereof has been set aside), then the holders of the Preference Shares shall be divested of the Appointing Rights (subject to revesting of the Appointing Rights in the event of any future Nonpayment pursuant to this Section 5(c)) and, if and when the Appointing Rights of the holders of the Preference Shares and any Appointing Preference Shares shall have ceased, the office of the Preference Share Directors (notwithstanding the class of directors such Preference Share Directors shall be a part of) shall terminate forthwith and the number of directors constituting the Board of Directors shall automatically be reduced by two.

6.     Amendment or Modification; Waiver .

(a)    To the extent permitted by applicable law, the Board of Directors may modify the terms of this Certificate of Designation without the consent of any holder of Preference Shares to:

(i)  evidence the succession of any Person to the obligations of the Company;
(ii)  add to the covenants for the benefit of holders of the Preference Shares or to surrender any of the rights or powers of the Company under the Preference Shares;

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(iii)  cure any ambiguity or correct or supplement any provisions that may be inconsistent, provided that such action shall not adversely affect the interest of the holders of the Preference Shares in any material respect; or
(iv)  make any other provision with respect to such matters or questions arising under this Certificate of Designation which the Company may deem desirable and which shall not adversely affect the interests of the holders of the Preference Shares in any material respect.

(b)    Except as provided below in this Section 6(b), this Certificate of Designation may be amended, modified or supplemented, and noncompliance in any particular instance with any provision of this Certificate of Designation or the Preference Shares may be waived, in each case with the affirmative vote or written consent of the holders of at least a majority of the aggregate liquidation preference of the Preference Shares then outstanding, including any modification occurring in connection with any merger or consolidation of the Company or otherwise.

Without the written consent or the affirmative vote of each holder of the Preference Shares affected thereby (in addition to the written consent or the affirmative vote of the holders of at least a majority of the aggregate liquidation preference of the Preference Shares then outstanding), an amendment or modification under this Section 6(b) may not:

(i)  change any Dividend Payment Date;
(ii)  reduce the rate of dividends payable on the Preference Shares, when, as and if declared by the Board of Directors;
(iii)  reduce the redemption price or alter the January 1, 2017 optional redemption date;
(iv)  change the place or currency of payment of the Preference Shares;
(v)  impair the right to institute suit for the enforcement of the Preference Shares; or
(vi)  change the percentage of liquidation preference of the Preference Shares whose holders must approve any amendment or modification.

7.     Liquidation Rights.

(a)    In the event of any liquidation, winding-up or dissolution of the Company, whether voluntary or involuntary, the holders of the Preference Shares shall be entitled to receive and to be paid out of the assets of the Company available for distribution to its shareholders, after satisfaction of liabilities of the Company and before any payment or distribution shall be made on the Ordinary Shares or any other class of shares ranking junior to the Preference Shares upon liquidation, winding-up or dissolution of the Company, the liquidation preference plus declared but unpaid dividends thereon, if any, without accumulation of any undeclared dividends (collectively, the ‘‘ Liquidation Distribution ’’).

(b)    After the payment to the holders of the Preference Shares of the Liquidation Distribution to which such holders are entitled as provided for in this Section 7, the holders of Preference Shares as such shall have no right or claim to any of the remaining assets of the Company.

(c)    If, upon any liquidation, winding-up or dissolution of the Company, whether voluntary or involuntary, the amounts payable with respect to the Preference Shares and any other share capital of the Company ranking on a parity with the Preference Shares upon liquidation, winding-up or dissolution of the Company are not paid in full, the holders of the Preference Shares and of such other share capital shall share ratably in any such distribution of assets of the Company in proportion to the full respective liquidation distributions to which they are entitled.

(d)    Neither the sale, assignment, transfer or lease of all or substantially all the assets or business of the Company nor the merger or consolidation of the Company into or with any other Person shall be deemed to be a liquidation, winding-up or dissolution, voluntary or involuntary, for the purposes of this Section 7.

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8.     Optional Redemption.

(a)    The Company may not redeem Preference Shares prior to January 1, 2017, except as provided in Section 8(b). On and after January 1, 2017, the Company may redeem the Preference Shares at its option, in whole or in part, upon notice given as provided in Section 8(c), at a redemption price equal to U.S.$25 per Preference Share, plus an amount equal to any declared and unpaid dividends (but with no amount in respect of any dividends that have not been declared prior to the Redemption Date), out of funds legally available for that purpose under Bermuda law and to the extent the Company has reasonable grounds to believe that it is, and after the payment would be, able to pay its liabilities as they become due.

(b)    Prior to January 1, 2017, the Company may redeem the Preference Shares at its option, in whole but not in part, if the Company has submitted to holders of its Ordinary Shares a proposal for a merger, amalgamation, or consolidation, arrangement, reconstruction or discontinuance, or if the Company submits any proposal for any other matter that, as a result of any change in Bermuda law after November 10, 2006, requires for its validation or effectuation an affirmative vote of the holders of the Preference Shares at the time outstanding, whether voting as a separate series or together with any other series or class of preference shares as a single class, upon not less than 30 calendar days nor more than 60 calendar days prior written notice to the relevant holders, in such form and given in such manner as to be in accordance with Section 8(c), at a redemption price per Preference Share equal to the greater of: (1) U.S.$25 per Preference Share and (2) the sum of the present value of U.S.$25 per Preference Share and the present value of all undeclared dividends for the Dividend Periods from the Redemption Date to and including the January 1, 2017 Dividend Payment Date, in each case, discounted to the Redemption Date on a quarterly basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate, as calculated by the Calculation Agent, plus 45 basis points, and in each case of (1) and (2), plus declared and unpaid dividends, (but with no amount in respect of any dividends that have not been declared prior to the Redemption Date), out of funds legally available for that purpose under Bermuda law and to the extent the Company has reasonable grounds to believe that it is, and after the payment would be, able to pay its liabilities as they become due.

(c)    Notice of each redemption of Preference Shares shall be given by first class mail, to the holders of the Company’s Preference Shares at their addresses set forth in the Register, mailed not less than 30 calendar days nor more than 60 calendar days prior to the Redemption Date. Notwithstanding the foregoing, if the Preference Shares are Global Preference Shares deposited with or on behalf of DTC, the Company may give such notice of optional redemption in any manner permitted by DTC.

(d)    A notice of redemption shall state:

(i)  the Redemption Date;
(ii)  the number of Preference Shares to be redeemed and, if less than all the Preference Shares held by such holder are to be redeemed, the number of Preference Shares to be redeemed from such holder;
(iii)  the CUSIP, ISIN or similar number or numbers of the Preference Shares to be redeemed;
(iv)  the redemption price and the amount of declared and unpaid dividends, if any; and
(v)  if certificated Preference Shares have been issued, the place or places where holders may surrender certificates evidencing the Preference Shares for payment of the redemption price.

(e)    On or prior to the Redemption Date, the Company will deposit with the Paying Agent an amount in immediately available funds sufficient to pay the aggregate redemption price plus any declared and unpaid dividends; provided that if such payment is deposited on the Redemption Date, it must be received by the Paying Agent by 10:00 a.m. (New York City time) on the Redemption Date. An amount equal to the redemption price and any declared and unpaid dividends shall be paid to the holders promptly following the later of (i) the Redemption Date and (ii) the time of book-entry transfer or surrender of the certificate(s) evidencing such Preference Shares to the Paying Agent, as applicable.

(f)    Any declared but unpaid dividends payable on a Redemption Date that occurs subsequent to the Dividend Record Date for a Dividend Period shall not be paid to the holder entitled to receive the

9




redemption price on the Redemption Date, but rather shall be paid to the holder of record of the redeemed shares on such Dividend Record Date relating to the Dividend Payment Date.

(g)    In case of any redemption of only part of the Preference Shares at the time outstanding, the Preference Shares to be redeemed shall be selected either pro rata or in such other manner as the Company may determine to be fair and equitable.

(h)    If notice of redemption has been duly given and the Paying Agent holds, on or before the Redemption Date, immediately available funds sufficient to pay the aggregate redemption price plus any declared and unpaid dividends, then, as of the Redemption Date:

(i)  dividends shall cease to be payable on such Preference Shares;
(ii)  such Preference Shares shall no longer be deemed outstanding; and
(iii)  all rights with respect to such Preference Shares shall cease and terminate, except only the right of the holders to receive an amount equal to the redemption price, plus any declared and unpaid dividends.

9.     Maturity.

The Preference Shares have no stated maturity. Accordingly, the Preference Shares shall remain outstanding perpetually, unless and until the Company elects to redeem them.

10.     Conversion Rights.

The Preference Shares are not convertible.

11.     Consolidation, Merger, Sale or Conveyance .

(a)    The Company covenants that it will not merge or amalgamate with or into, consolidate with or convert into any other entity or sell, assign, transfer, lease or convey all or substantially all of its properties and assets to any person or entity, unless:

(i)  either the Company shall be the continuing corporation, or the successor (if other than the Company) shall be a corporation organized under the laws of the United States of America or a State thereof or the District of Columbia, Bermuda or any country which is, on the date of this Certificate of Designation, a member of the Organization of Economic Cooperation and Development and the Preference Shares are converted into or exchanged for, in accordance with applicable law, perpetual non-cumulative preference shares of the successor corporation with substantially the same rights, powers, preferences and privileges; and
(ii)  the Company or such successor corporation, as the case may be, shall not, immediately after such merger, amalgamation, consolidation, conversion, sale, assignment, transfer, lease or conveyance, be in default of any obligation under the Preference Shares.

(b)    In case of any such merger, amalgamation, consolidation, conversion, sale, assignment, transfer, lease or conveyance and upon any conversion of securities into a successor corporation in accordance with (a) above, such successor corporation shall succeed to and be substituted for the Company with the same effect as if it had been named herein as the Company. Such successor Person thereupon may cause to be signed, and may issue either in its own name or in the name of the Company, any or all of the certificates evidencing Preference Shares issuable hereunder which theretofore shall not have been signed by the Company. All the certificates issued shall in all respects have the same legal rank and benefit under this Certificate of Designation as the certificates theretofore or thereafter issued in accordance with the terms of this Certificate of Designation as though all of such certificates had been issued on the Issue Date.

In case of any such merger, amalgamation, consolidation, conversion, sale, assignment, transfer, lease or conveyance such change in phraseology and form (but not in substance) may be made in the certificates evidencing securities for which the Preference Shares have been exchanged thereafter to be issued as may be appropriate.

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12.     Currency of Payments .

Any payments with respect to the Preference Shares shall be paid in cash in United States dollars in immediately available funds.

13.     Form.

(a)    The Preference Shares shall be issued initially in the form of one or more fully registered global certificates with the global securities legend set forth in Exhibit A hereto (‘‘ Global Preference Shares ’’), each as set forth on the form of Preference Shares certificate attached hereto as Exhibit A which is hereby incorporated in and expressly made a part of this Certificate of Designation. The Global Preference Shares certificate may have notations, legends or endorsements required by law, stock exchange rules, agreements to which the Company is subject, if any, or usage (provided that any such notation, legend or endorsement is in a form acceptable to the Company). The Global Preference Shares shall be deposited on behalf of the holders of the Preference Shares represented thereby with the Registrar, as custodian for DTC (or with such other custodian as DTC may direct), and registered in the name of DTC or a nominee of DTC, duly executed by the Company and countersigned by the Registrar as hereinafter provided. The aggregate number of Preference Shares represented by Global Preference Shares may from time to time be increased or decreased by adjustments made on the records of the Registrar and DTC or its nominee as hereinafter provided.

In the event Global Preference Shares are deposited with or on behalf of DTC, the Company shall execute, and the Registrar shall countersign and deliver, initially one or more Global Preference Shares certificates that (a) shall be registered in the name of Cede & Co. or other nominee of the Depositary and (b) shall be delivered by the Registrar to DTC or pursuant to DTC’s instructions or held by the Registrar as custodian for DTC. Members of, or participants in, DTC (‘‘ Agent Members ’’) shall have no rights under this Certificate of Designation with respect to any Global Preference Shares held on their behalf by DTC or by the Registrar as the custodian of DTC or under such Global Preference Shares, and DTC may be treated by the Company, the Registrar and any agent of the Company or the Registrar as the absolute owner of such Global Preference Shares for all purposes whatsoever. Notwithstanding the foregoing, nothing herein shall prevent the Company, the Registrar or any agent of the Company or the Registrar from giving effect to any written certification, proxy or other authorization furnished by DTC or impair, as between DTC and its Agent Members, the operation of customary practices of DTC governing the exercise of the rights of a holder of a beneficial interest in any Global Preference Shares.

(b)    Owners of beneficial interests in Global Preference Shares shall not be entitled to receive physical delivery of certificated Preference Shares, unless:

(i)  DTC is unwilling or unable to continue as Depositary for the Global Preference Shares and the Company does not appoint a qualified replacement for DTC within 90 calendar days;
(ii)  DTC ceases to be a ‘‘clearing agency’’ registered under the Exchange Act and the Company does not appoint a qualified replacement for DTC within 90 calendar days; or
(iii)  the Company decides to discontinue the use of book-entry transfer through DTC (or any successor Depositary).

In any such case, the Global Preference Shares shall be exchanged in whole for certificated Preference Shares in registered form, with the same terms and of an equal aggregate liquidation preference (unless the Company determines otherwise in accordance with applicable law).  Certificated Preference Shares shall be registered in the name or names of the Person or Person specified by DTC in a written instrument to the Registrar.

(c)    An Officer shall sign the Preference Shares certificate for the Company by manual or facsimile signature.  If the Officer whose signature is on a Preference Shares certificate no longer holds that office at the time the Registrar countersigns the Preference Shares certificate, the Preference Shares certificate shall be valid nevertheless.

11




A Preference Shares certificate shall not be valid until an authorized signatory of the Registrar signs the Preference Shares certificate by manual or facsimile signature. The signature shall be conclusive evidence that the Preference Shares certificate has been countersigned under this Certificate of Designation.

14.     Registration; Transfer.

(a)    Notwithstanding any provision to the contrary herein, so long as a Global Preference Share remains outstanding and is held by or on behalf of the Depositary, transfers of a Global Preference Share, in whole or in part, or of any beneficial interest therein, shall only be made in accordance with this Section 14.

(b)    Transfers of a Global Preference Share shall be limited to transfers of such Global Preference Share in whole, but not in part, to nominees of the Depositary or to a successor of the Depositary or such successor’s nominee.

15.     Calculation in Respect of Preference Shares .

The Company will be responsible for making all calculations called for in respect of the Preference Shares, including, but not limited to, the determination of the dividends payable on the Preference Shares. Any calculations made in good faith and without manifest error will be final and binding on holders. The Company or its agents will be required to deliver to the Paying Agent a schedule of its calculations and the Paying Agent will be entitled to rely upon the accuracy of such calculations without independent verification. The Paying Agent will forward such calculations to any holder upon the request of the holder.

16.     Severability .

In the event any provision of this Certificate of Designation shall be invalid, unenforceable or illegal, then, to the fullest extent permitted by applicable law, the validity, enforceability and legality of the remaining provisions shall not in any way be affected or impaired thereby.

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IN WITNESS WHEREOF, the Company has caused this Certificate of Designation to be signed and attested by the undersigned this 15th day of November, 2006.


  ASPEN INSURANCE HOLDINGS LIMITED
  By:                                                                               
Attest:                                                                                  

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EXHIBIT A

FORM OF
7.401% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES

FACE OF SECURITY

[UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (‘‘DTC’’), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO., OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC) ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO. HAS AN INTEREST HEREIN.

TRANSFERS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO TRANSFERS IN WHOLE, BUT NOT IN PART, TO NOMINEES OF DTC OR TO A SUCCESSOR THEREOF OR SUCH SUCCESSOR’S NOMINEE AND TRANSFERS OF PORTIONS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN THE CERTIFICATE OF DESIGNATION REFERRED TO BELOW.

IN CONNECTION WITH ANY TRANSFER, THE HOLDER WILL DELIVER TO THE REGISTRAR AND TRANSFER AGENT SUCH CERTIFICATES AND OTHER INFORMATION AS SUCH REGISTRAR AND TRANSFER AGENT MAY REASONABLY REQUIRE TO CONFIRM THAT THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS.] 1

1   This legend should be included only if the share certificate evidences Global Preference Shares.

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Certificate Number Number of
Preference Shares
[        ] [        ]

CUSIP NO.:[        ]

7.401% Perpetual Non-Cumulative Preference Shares
(par value 0.15144558¢ per share)
(liquidation preference U.S.$25 per Preference Share)

of

  ASPEN INSURANCE HOLDINGS LIMITED  

ASPEN INSURANCE HOLDINGS LIMITED, a Bermudian company (the ‘‘Company’’), hereby certifies that [                            ] (the ‘‘Holder’’) is the registered owner of [                            ] 1 [                    , or such number as is indicated in the records of the Registrar and the Depository,] 2 fully paid and non-assessable preference shares of the Company designated the 7.401% Perpetual Non-Cumulative Preference Shares, with a par value of 0.15144558¢ per share and a liquidation preference of U.S.$25 per share (the ‘‘Preference Shares’’). The Preference Shares are transferable on the books and records of the Registrar, in person or by a duly authorized attorney, upon surrender of this certificate duly endorsed and in proper form for transfer. The designations, rights, privileges, restrictions, preferences and other terms and provisions of the Preference Shares represented hereby are issued and shall in all respects be subject to the provisions of the Certificate of Designation dated November 15, 2006, as the same may be amended from time to time (the ‘‘Certificate of Designation’’). Capitalized terms used herein but not defined shall have the meaning given them in the Certificate of Designation. The Company will provide a copy of the Certificate of Designation to a Holder without charge upon written request to the Company at its principal place of business.

Reference is hereby made to select provisions of the Preference Shares set forth on the reverse hereof, and to the Certificate of Designation, which select provisions and the Certificate of Designation shall for all purposes have the same effect as if set forth at this place.

Upon receipt of this certificate, the Holder is bound by the Certificate of Designation and is entitled to the benefits thereunder.

Unless the Registrar has properly countersigned, these Preference Shares shall not be entitled to any benefit under the Certificate of Designation or be valid or obligatory for any purpose.

1   This phrase should be included only if the share certificate evidences certificated Preference Shares.
2   This phrase should be included only if the share certificate evidences Global Preference Shares.

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IN WITNESS WHEREOF, the Company has executed this certificate this               day of               ,               .


  ASPEN INSURANCE HOLDINGS LIMITED
  By:                                                                               
  Name:
  Title:

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REGISTRAR’S COUNTERSIGNATURE

These are Preference Shares referred to in the within-mentioned Certificate of Designation.

Dated:


  MELLON INVESTOR SERVICES LLC, as
Registrar,
  By:                                                                         
  Authorized Signatory

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REVERSE OF SECURITY

Dividends on each Preference Share shall be payable at the rate provided in the Certificate of Designation.

The Preference Shares shall be redeemable at the Company’s option in the manner and accordance with the terms set forth in the Certificate of Designation.

The Company shall furnish without charge to each holder who so requests the powers, designations, preferences and relative, participating, optional or other special rights of each class or series of share capital and the qualifications, limitations or restrictions of such preferences and/or rights.

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ASSIGNMENT

FOR VALUE RECEIVED, the undersigned assigns and transfers the Preference Shares evidenced hereby to:

(Insert assignee’s social security or tax identification number)

(Insert address and zip code of assignee)

and irrevocably appoints:

agent to transfer the Preference Shares evidenced hereby on the books of the Transfer Agent. The agent may substitute another to act for him or her.

Date:__________________

Signature:__________________________

(Sign exactly as your name appears on the other side of this Preference Shares Certificate)

Signature Guarantee:__________________

(Signature must be guaranteed by an ‘‘eligible guarantor institution’’ that is a bank, stockbroker, savings and loan association or credit union meeting the requirements of the Transfer Agent, which requirements include membership or participation in the Securities Transfer Agents Medallion Program (‘‘STAMP’’) or such other ‘‘signature guarantee program’’ as may be determined by the Transfer Agent in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange Act of 1934, as amended.)

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Exhibit 4.3

Replacement Capital Covenant, dated as of November 15, 2006 (this ‘‘ Replacement Capital Covenant ’’), by Aspen Insurance Holdings Limited, a limited company duly organized and existing under the laws of Bermuda (together with its successors and assigns, the ‘‘ Company ’’), in favor of and for the benefit of each Covered Debtholder (as defined below).

Recitals

A.     On the date hereof, the Company is issuing 8,000,000 Perpetual Non-Cumulative Preference Shares, liquidation preference $25 per share (the ‘‘ Preference Shares ’’). The Company may from time to time elect to issue additional Preference Shares, and all such additional Preference Shares would be deemed to form a single series with the 8,000,000 Preference Shares being issued on the date hereof. In such event, the term ‘‘Preference Shares’’ shall include these additional Preference Shares.

B.     The Preference Shares and this Replacement Capital Covenant are described in the Prospectus Supplement, dated November 10, 2006, filed with the United States Securities and Exchange Commission (the ‘‘ Commission ’’) by the Company pursuant to Rule 424(b)(2) on November 13, 2006 relating to the offering of Preference Shares.

C.     The Company is entering into and disclosing the content of this Replacement Capital Covenant in the manner provided below with the intent that the covenants provided for in this Replacement Capital Covenant be enforceable by each Covered Debtholder and that the Company be estopped from disregarding the covenants in this Replacement Capital Covenant, in each case to the fullest extent permitted by applicable law.

D.     The Company acknowledges that reliance by each Covered Debtholder upon the covenants in this Replacement Capital Covenant is reasonable and foreseeable by the Company and that, were the Company to disregard its covenants in this Replacement Capital Covenant, each Covered Debtholder would have sustained an injury as a result of its reliance on such covenants.

NOW, THEREFORE, the Company hereby covenants and agrees as follows in favor of and for the benefit of each Covered Debtholder.

SECTION 1. Definitions . Capitalized terms used in this Replacement Capital Covenant (including the Recitals) have the meanings set forth in Schedule I hereto.

SECTION 2. Limitations on Redemption or Repurchase of Preference Shares . The Company hereby promises and covenants to and for the benefit of each Covered Debtholder that, on or before November 15, 2046, neither the Company nor any of its subsidiaries shall redeem or repurchase all or any part of the Preference Shares, except to the extent that the applicable redemption or repurchase price does not exceed the sum of the following amounts:

(i) the Applicable Percentage of the aggregate amount of net cash proceeds received by the Company and its Subsidiaries from the sale of Ordinary Shares and rights to acquire Ordinary Shares to Persons other than the Company and its Subsidiaries; plus

(ii) 100% of the aggregate amount of net cash proceeds received by the Company and its Subsidiaries from the sale of Mandatorily Convertible Preference Shares and Debt Exchangeable into Equity to Persons other than the Company and its Subsidiaries; plus

(iii) 100% of the aggregate amount of net cash proceeds received by the Company and its Subsidiaries from the sale of any other Qualifying Replacement Capital Securities to Persons other than the Company and its Subsidiaries;

in each case during the six months prior to the applicable redemption or repurchase.

SECTION 3. Covered Debt .

(a)    The Company represents and warrants that the Initial Covered Debt is Eligible Debt.

(b)    The Company shall follow the procedures set forth in Section 3(c) for redesignating the Covered Debt in the event that the Covered Debt then in effect is Eligible Senior Debt and the




Company subsequently issues Eligible Subordinated Debt, in which case the Company shall redesignate such newly-issued Eligible Subordinated Debt as the Covered Debt. In addition, the Company shall follow the procedures set forth in Section 3(c) for redesignating the Covered Debt on (i) the date that is two years prior to the final maturity date of the Covered Debt then in effect or (ii) the applicable redemption or repurchase date in the event the Company elects to redeem, or the Company or a Subsidiary of the Company elects to repurchase, such Covered Debt in whole or in part with the consequence that after giving effect to such redemption or repurchase, the outstanding principal amount of such Covered Debt is less than $100,000,000.

(c)    During the 30-calendar-day period immediately preceding any Redesignation Date with respect to the Covered Debt then in effect, the Company shall identify the series of Eligible Debt that will become the Covered Debt on and after such Redesignation Date in accordance with the following procedures:

(i) the Company shall identify each series of its then outstanding long-term indebtedness for money borrowed that is Eligible Debt;

(ii) if only one series of the Company’s then outstanding long-term indebtedness for money borrowed is Eligible Debt, such series shall become the Covered Debt commencing on the related Redesignation Date; and

(iii) if the Company has more than one outstanding series of long-term indebtedness for money borrowed that is Eligible Debt, the series that has the latest occurring final maturity date shall become the Covered Debt on the related Redesignation Date.

The series of outstanding long-term indebtedness for money borrowed that is determined to be Covered Debt pursuant to clause (c)(ii) or (c)(iii) above shall be the Covered Debt for purposes of this Replacement Capital Covenant for the period commencing on the related Redesignation Date and continuing to, but not including, the Redesignation Date as of which a new series of outstanding long-term indebtedness is next determined to be the Covered Debt pursuant to the procedures set forth in this Section 3(c).

In connection with the identification of any new series of Covered Debt, the Company shall give the notices and/or make the filings or website postings provided for in Section 3(d) within the time frame provided for in such section.

(d)     Notice . In order to give effect to the intent of the Company described in Recital C, the Company covenants that:

(i) simultaneously with the execution of this Replacement Capital Covenant or as soon as practicable after the date hereof, it shall give notice to the Holder(s) of the Initial Covered Debt, in the manner provided in the indenture relating to the Initial Covered Debt, of this Replacement Capital Covenant and the rights granted to such Holder(s) hereunder;

(ii) if the Covered Debt includes securities issued in the United States, the Company shall file a Form 8-K under the Securities Exchange Act, and if Covered Debt includes securities issued outside of the United States listed on an offshore exchange, the Company shall file an informational report with such exchange, in each case, containing a description of the covenant set forth in Section 2 and identifying the series of long-term indebtedness for borrowed money that is Covered Debt as of the date of such filing or report, and including a copy of this Replacement Capital Covenant as an exhibit;

(iii) it shall, if a series of the Company’s long-term indebtedness for money borrowed (1) becomes Covered Debt or (2) ceases to be Covered Debt, (A) give notice of such occurrence within 30 calendar days to the holders of such long-term indebtedness for money borrowed in the manner provided for in the indenture, fiscal agency agreement or other instrument under which such long-term indebtedness for money borrowed was issued and (B) if and so long as it is a reporting company under the Securities Exchange Act, report such change by making the filing or report in the manner specified in clause (d)(ii), as applicable;

(iv) if and so long as it is a reporting company under the Securities Exchange Act, the Company shall include in each annual report filed with the Commission on Form 10-K under the

2




Securities Exchange Act a description of the covenant set forth in Section 2 and identify the series of long-term indebtedness for borrowed money that is Covered Debt as of the date such Form 10-K is filed with the Commission;

(v) if and so long as it is not a reporting company under the Securities Exchange Act, it shall post on its website the information required by clauses (d)(ii), (d)(iii) and (d)(iv); and

(vi) promptly upon request by any Holder of Covered Debt, provide such Holder with an executed copy of this Replacement Capital Covenant.

SECTION 4. Termination, Amendment and Waiver .

(a)    The obligations of the Company pursuant to this Replacement Capital Covenant shall remain in full force and effect until the earliest date (the ‘‘ Termination Date ’’) to occur of:

(i) November 15, 2046;

(ii) the date, if any, on which the Holder(s) of a majority by principal amount of the then-effective series of Covered Debt consent or agree in writing to the termination of this Replacement Capital Covenant and the obligations of the Company hereunder;

(iii) the date on which the Company does not have any series of outstanding Eligible Subordinated Debt or Eligible Senior Debt (in each case without giving effect to the rating requirement in clause (b) of the definition of each such term); and

(iv) the date on which the Company does not have any outstanding Preference Shares.

From and after the Termination Date, the obligations of the Company pursuant to this Replacement Capital Covenant shall be of no further force and effect.

(b)    This Replacement Capital Covenant may be amended or supplemented from time to time by a written instrument signed by the Company with the consent of the Holder(s) of a majority by principal amount of the then-effective series of Covered Debt, provided that this Replacement Capital Covenant may be amended or supplemented from time to time by a written instrument signed only by the Company (and without the consent of the Holder(s) of the then-effective series of Covered Debt) if:

(i) the effect of such amendment or supplement is solely to (A) eliminate Ordinary Shares or Mandatorily Convertible Preference Shares as a security or securities covered by Sections 2(i) and (ii), provided that the Company has been advised in writing by a nationally recognized independent accounting firm that there is more than an insubstantial risk that the failure to do so would result in a reduction in the Company’s earnings per share as calculated for financial reporting purposes or (B) impose additional restrictions on the ability of the Company to redeem or repurchase Preference Shares in any circumstance, including extending the termination date specified in Section 4(a)(i), the dates specified in the definition of Applicable Percentage and the dates specified in the definition of Qualifying Replacement Capital Securities, and in the case of each of clauses (A) and (B) such amendment or supplement is not adverse to the Holder(s) of the then-effective series of Covered Debt; or

(ii) such amendment or supplement is not adverse to the Holder(s) of the then-effective series of Covered Debt and an officer of the Company has delivered to the Holder(s) of the then effective series of Covered Debt in the manner provided for in the indenture, fiscal agency agreement or other instrument with respect to such Covered Debt a written certificate stating that, in his or her determination, such amendment or supplement is not adverse to the Holder(s) of the then-effective series of Covered Debt.

(c)    For purposes of Sections 4(a) and 4(b), the Holder(s) whose consent or agreement is required to terminate, amend or supplement the obligations of the Company under this Replacement Capital Covenant shall be the Holder(s) of the then-effective Covered Debt as of a record date established by the Company that is not more than 30 calendar days prior to the date on which the Company proposes that such termination, amendment or supplement becomes effective.

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SECTION 5. Miscellaneous .

(a)      This Replacement Capital Covenant shall be governed by, and construed in accordance with, the laws of the State of New York, without giving effect to its conflicts of law principles.

(b)    This Replacement Capital Covenant shall be binding upon the Company and its successors and assigns and shall inure to the benefit of the Covered Debtholders as they exist from time-to-time (it being understood and agreed by the Company that any Person who is a Covered Debtholder at the time such Person initiates a claim or proceeding to enforce its rights under this Replacement Capital Covenant after the Company has violated its covenants in Section 2 and before the series of long-term indebtedness for money borrowed held by such Person is no longer Covered Debt, such Person’s rights under this Replacement Capital Covenant shall not terminate by reason of such series of long-term indebtedness for money borrowed no longer being Covered Debt until the termination of such claim or proceeding). Except as specifically provided herein, this Replacement Capital Covenant shall have no other beneficiaries, and no other Persons are entitled to rely on this Replacement Capital Covenant.

(c)    All demands, notices, requests and other communications to the Company under this Replacement Capital Covenant shall be deemed to have been duly given and made if in writing and:

(i) if served by personal delivery upon the Company, on the day so delivered (or, if such day is not a Business Day, the next succeeding Business Day);

(ii) if delivered by registered post or certified mail, return receipt requested, or sent to the Company by a national or international courier service, on the date of receipt by the Company (or, if such date of receipt is not a Business Day, the next succeeding Business Day); or

(iii) if sent by telecopier, on the day telecopied, or if not a Business Day, the next succeeding Business Day, provided that the telecopy is promptly confirmed by telephone confirmation thereof,

and in each case to the Company at the address set forth below, or at such other address as the Company may thereafter notify to Covered Debtholders or post on its website as the address for notices under this Replacement Capital Covenant:

Aspen Insurance Holdings Limited
Maxwell Roberts Building
1 Church Street
Hamilton HM 11
Bermuda

Attention: Julian Cusack, Chief Financial Officer
Facsimile No: 441-295-1829

4




IN WITNESS WHEREOF, the Company has caused this Replacement Capital Covenant to be executed by its duly authorized officer, as of the day and year first above written.

ASPEN INSURANCE HOLDINGS LIMITED
By:                                             
       Name:
       Title:

5




Schedule 1

Definitions

‘‘ Alternative Payment Mechanism ’’ means, with respect to any securities, that such securities or related transaction agreements include a provision to the effect that, upon the occurrence of certain events specified in such securities or related transaction agreements, the Company:

(a) shall (i) sell, or use its commercially reasonable efforts to sell, its Ordinary Shares, rights to purchase Ordinary Shares or Qualifying Preference Shares, unless a Market Disruption Event has occurred and is continuing, in amount such that the net proceeds of such sale equal or exceed the amount of accumulated and unpaid deferred Distributions on such securities (including any compounded amounts) and (ii) apply the proceeds of such sale to pay such deferred Distributions; and

(b) shall not, from and after the occurrence of any of such specified events until, but excluding, the End Date, pay any accumulated and unpaid deferred Distributions on such securities to the extent such Distributions exceed the net proceeds of such sale;

provided that the aggregate net proceeds from the issuance or sale of Qualifying Preference Shares that may be used to pay deferred Distributions shall not exceed 25% of the initial aggregate liquidation preference or principal amount of the Qualifying Replacement Capital Securities; and provided further that the number of any Ordinary Shares that may be issued or sold, together with the number of Ordinary Shares underlying any rights to purchase Ordinary Shares that may be issued or sold, to pay deferred Distributions attributable to the first five years of any deferral period (including compounded amounts thereon), together with the aggregate number of Ordinary Shares and number of Ordinary Shares underlying rights to purchase Ordinary Shares so issued and sold previously, may be limited to an amount equal to 2% of the number of Ordinary Shares outstanding contemporaneously with the date of such issuance or sale.

‘‘ Applicable Percentage ’’ means:

(a) 133.33% with respect to any redemption or repurchase prior to November 15, 2016;

(b) 200% with respect to any redemption or repurchase on or after November 15, 2016 and prior to November 15, 2036; and

(c) 400% with respect to any redemption or repurchase on or after November 15, 2036.

‘‘ Business Day ’’ means a day that is a Monday, Tuesday, Wednesday, Thursday or Friday and is not a day on which banking institutions in New York City or Bermuda generally are authorized or obligated by law or executive order to close.

‘‘ Commission ’’ has the meaning specified in Recital B.

‘‘ Company ’’ has the meaning specified in the introduction to this instrument.

‘‘ Covered Debt ’’ means:

(a) at the date of this Replacement Capital Covenant and continuing to, but not including, the first Redesignation Date, the Initial Covered Debt; and

(b) thereafter, commencing with each Redesignation Date and continuing to, but not including, the next succeeding Redesignation Date, the Eligible Debt identified pursuant to Section 3(b) as the Covered Debt for such period.

‘‘ Covered Debtholder ’’ means each Person (whether a Holder or a beneficial owner holding through a participant in a clearing agency) that holds Covered Debt, for so long as the long-term indebtedness for money borrowed of the Company that such Person holds is Covered Debt.

‘‘ Debt Exchangeable for Equity ’’ means any security or combination of securities that:

(a) gives the holder a beneficial interest in (i) Most Junior Subordinated Debt Securities that are Non-Cash Cumulative and (ii) a stock purchase contract that will result in the holder of the

I-1




security acquiring a beneficial interest in Ordinary Shares or Qualifying Preference Shares; provided that the number of Ordinary Shares to be acquired pursuant to the stock purchase contract shall be within a range that is established at the time of issuance of the stock purchase contract;

(b) includes a remarketing feature pursuant to which the Most Junior Subordinated Debt Securities are remarketed to new investors within five years from the date of issuance of the security (or combination of securities) or earlier in the event of an early settlement event based on one or more financial tests or other express terms set forth in the terms of such securities or related transaction agreements;

(c) provides for the proceeds raised in the remarketing to be used to satisfy the holder’s payment obligations (if not otherwise fulfilled) in respect of the required purchase of Ordinary Shares or Qualifying Preference Shares;

(d) includes a replacement capital covenant substantially similar to this Replacement Capital Covenant, provided that such replacement capital covenant will apply to such security (or combination of securities) and to any such Qualifying Preference Shares and will not include Debt Exchangeable for Equity in the definition of ‘‘Qualifying Replacement Capital Securities’’;

(e) after the issuance of such Ordinary Shares or Qualifying Preference Shares, provides the holder of the security with a beneficial interest in such Ordinary Shares or Qualifying Preference Shares;

(f) includes a provision granting the Company a security interest in the Most Junior Subordinated Debt Securities to secure the holder’s obligation to purchase such Ordinary Shares or Qualifying Preference Shares; and

(g) includes a provision defining a failed remarketing and specifying that the consequence of a failed remarketing will be that such Ordinary Shares or Qualifying Preference Shares will be acquired in exchange for the Most Junior Subordinated Debt Securities.

‘‘ Distributions ’’ means, as to any security or combination of securities, dividends, interest payments or other income distributions to the holders thereof that are not Subsidiaries of the Company.

‘‘ Eligible Debt ’’ means, at any time, Eligible Subordinated Debt or, if no Eligible Subordinated Debt is then outstanding, Eligible Senior Debt.

‘‘ Eligible Senior Debt ’’ means, at any time in respect of the Company, each series of then-outstanding long-term indebtedness for money borrowed that:

(a) upon a bankruptcy, liquidation, dissolution or winding up of the Company, ranks most senior among the Company’s then outstanding classes of indebtedness for money borrowed;

(b) is then assigned a rating by at least one NRSRO (provided that this clause (b) shall apply on a Redesignation Date only if on such date the Company has outstanding senior long-term indebtedness for money borrowed that satisfies the requirements of clauses (a), (c), (d) and (e) that is then assigned a rating by at least one NRSRO);

(c) will not mature within two years;

(d) has an outstanding principal amount of not less than $100,000,000; and

(e) was issued through or with the assistance of a commercial or investment banking firm or firms acting as underwriters, initial purchasers or placement or distribution agents.

For purposes of this definition as applied to securities with a CUSIP, ISIN or Common Code number, each issuance of long-term indebtedness for money borrowed that has (or, if such indebtedness is held by a trust or other intermediate entity established directly or indirectly by the Company, the securities of such intermediate entity that have) a separate CUSIP, ISIN or Common Code number shall be deemed to be a series of the Company’s long-term indebtedness for money borrowed that is separate from each other series of such indebtedness.

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‘‘ Eligible Subordinated Debt ’’ means, at any time in respect of the Company, each series of then-outstanding long-term indebtedness for money borrowed that:

(a) upon a bankruptcy, liquidation, dissolution or winding up of the Company, ranks subordinate to the Company’s then outstanding classes of indebtedness for money borrowed that ranks most senior;

(b) is then assigned a rating by at least one NRSRO (provided that this clause (b) shall apply on a Redesignation Date only if on such date the Company has outstanding subordinated long-term indebtedness for money borrowed that satisfies the requirements in clauses (a), (c), (d) and (e) that is then assigned a rating by at least one NRSRO);

(c)    will not mature within two years;

(d) has an outstanding principal amount of not less than $100,000,000, and

(e) was issued through or with the assistance of a commercial or investment banking firm or firms acting as underwriters, initial purchasers or placement or distribution agents.

For purposes of this definition as applied to securities with a CUSIP, ISIN or Common Code number, each issuance of long-term indebtedness for money borrowed that has (or, if such indebtedness is held by a trust or other intermediate entity established directly or indirectly by the Company, the securities of such intermediate entity that have) a separate CUSIP, ISIN or Common Code number shall be deemed to be a series of the Company’s long-term indebtedness for money borrowed that is separate from each other series of such indebtedness.

‘‘ End Date ’’ means, with respect to any securities, the earliest to occur of:

(a) the Company’s failure to pay Distributions (including, without limitation, all deferred and accumulated amounts) in full for ten years;

(b) any liquidation, dissolution, winding up, reorganization, insolvency, receivership or proceeding under any bankruptcy law with respect to the Company;

(c) an event of default and acceleration with respect to such securities; and

(d) the final maturity of such securities.

‘‘ Holder ’’ means, as to the Covered Debt then in effect, each holder of such Covered Debt as reflected on the securities register maintained by or on behalf of the Company with respect to such Covered Debt.

‘‘ Initial Covered Debt ’’ means the Company’s 6.00% Senior Notes Due August 15, 2014 issued in the aggregate principal amount of $250,000,000.

‘‘ Intent-Based Replacement Disclosure ’’ means, with respect to any security or combination of securities that the Company has publicly stated its intention, either in the prospectus or other offering document under which such securities were initially offered for sale or in filings with the Commission made by the Company under the Securities Exchange Act prior to or contemporaneously with the issuance of such securities, that the Company will repay, redeem or repurchase such securities or, in the case of any securities that are convertible or exchangeable in whole or in part into cash, will pay any such cash in respect of such securities only if it has received an amount of net proceeds at least equal to the applicable repayment, redemption or repurchase price of such securities or such cash payment from the offer and sale of securities issued by the Company that are as or more equity-like than such securities, within six months prior to the applicable repayment, redemption or repurchase date or applicable cash payment date.

‘‘ Limitation on Distributions in Bankruptcy Provision ’’ means, with respect to any securities of the Company, provisions in the terms thereof or of the related transaction agreements that, upon any liquidation, dissolution, winding up, reorganization or in connection with any insolvency, receivership or proceeding under any bankruptcy law with respect to the Company, limit the claim of the holders of such securities (other than Qualifying Preference Shares) for Distributions (or in the case of

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securities containing a Mandatory Trigger Provision, Distributions that accumulate during a period in which the Company fails to satisfy one or more financial tests set forth in the terms of such securities or related transaction agreements) to:

(a) in the case of securities not permitting the issuance and sale of Qualifying Preference Shares pursuant to an Alternative Payment Mechanism, 25% of the principal amount of such securities then outstanding; or

(b) in all other cases, two years of accumulated and unpaid Distributions (including compounded amounts thereon).

‘‘ Mandatorily Convertible Preference Shares ’’ means preference shares of the Company with:

(a) no prepayment obligation on the part of the Company, whether at the election of the holders or otherwise; and

(b) a requirement that the preference shares convert into a number of Ordinary Shares within three years from the date of the issuance of the preference shares at a conversion ratio within a range established at the time of issuance of the preference shares.

‘‘ Mandatory Deferral Provision ’’ means, with respect to any securities of the Company, a provision in the terms thereof or of the related transaction agreements that prohibit the Company from paying any Distributions on such securities upon the failure, and for so long as the failure continues to occur, by the Company to satisfy one or more financial tests set forth in the terms of such securities or related transaction agreements.

‘‘ Mandatory Trigger Provision ’’ means, with respect to any securities of the Company, provisions in the terms thereof or of the related transaction agreements that:

(a) (i) include an Alternative Payment Mechanism that becomes effective within two years of a failure to satisfy one or more financial tests set forth in the terms of such securities or related transaction agreements or (ii) in the case of Qualifying Preference Shares, include provisions that, from and after the occurrence of the failure to satisfy any of such financial tests until, but excluding, the End Date, prohibit the Company from paying any deferred Distributions in an amount that exceeds the net proceeds of the sale of Ordinary Shares, rights to purchase Ordinary Shares or Qualifying Preference Shares;

(b) in the case of securities other than Qualifying Preference Shares, prohibit the Company from repurchasing any of its Ordinary Shares prior to the date six months after the Company has paid all deferred Distributions in full; and

(c) include a Limitation on Distributions in Bankruptcy Provision.

No remedy other than Permitted Remedies will arise by the terms of such securities or related transaction agreements in favor of the holders of such securities as a result of the Company’s failure to pay Distributions because of the Mandatory Trigger Provision or as a result of the Company’s exercise of its right under an Optional Deferral Provision until Distributions have been deferred for at least ten years.

‘‘ Market Disruption Events ’’ means the occurrence or existence of any of the following events or sets of circumstances:

(a) trading in securities generally on the New York Stock Exchange or any other national securities exchange or over-the-counter market on which the Company’s Ordinary Shares and/or preference shares are then listed or traded shall have been suspended or its settlement generally shall have been materially disrupted;

(b) the Company would be required to obtain the consent or approval of its shareholders or a regulatory body (including, without limitation, any securities exchange) or governmental authority to issue the applicable securities of the Company and the Company fails to obtain such consent or approval notwithstanding its commercially reasonable efforts to obtain such consent or approval;

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(c) there shall have occurred such a material adverse change in domestic or international economic, political or financial conditions (including from terrorist activities), or the effect of international conditions on the financial markets in the United States that materially disrupts trading in securities generally on the New York Stock Exchange or any other national securities exchange or over-the-counter market on which the Company’s Ordinary Shares and/or preference shares are then listed or traded, or the issuance and sale of the Company’s Ordinary Shares and/or preference shares; or

(d) an event occurs and is continuing as a result of which the offering document for the Ordinary Shares, rights to purchase Ordinary Shares and/or Qualifying Preference Shares would, in the Company’s reasonable judgment, contain an untrue statement of a material fact or omit to state a material fact required to be stated in such offering document or necessary to make the statements in such offering document not misleading and either (i) the disclosure of such event, in the Company’s reasonable judgment, would have a material adverse effect on its business or (ii) the disclosure relates to a previously undisclosed proposed or pending material business transaction, the disclosure of which would impede the Company’s ability to consummate such transaction; provided that one or more events described in this clause (d) shall not constitute a Market Disruption Event for a period longer than six months.

‘‘ Most Junior Subordinated Debt Securities ’’ mean debt securities of the Company that rank upon a liquidation, dissolution or winding-up of the Company junior to all of the Company’s other long-term indebtedness for money borrowed (other than the Company’s long-term indebtedness for money borrowed from time to time outstanding that by its terms ranks pari passu with such securities) and pari passu with the claims of the Company’s trade creditors.

‘‘ Non-Cash Cumulative ’’ means, with respect to any securities of the Company, that the securities include:

(a) an Optional Deferral Provision;

(b) an Alternative Payment Mechanism that becomes effective after the Company has deferred in whole or in part payment of Distributions on such securities for up to five years; and

(c) a Limitation on Distributions in Bankruptcy Provision.

‘‘ Non-Cumulative ’’ means, with respect to any securities of the Company, that either:

(a) the Company may elect not to make any number of periodic Distributions or interest payments without any remedy arising under the terms of the securities or related agreements in favor of the holders, other than Permitted Remedies; or

(b) except for purposes of the definition of ‘‘Qualifying Preference Shares,’’ the securities are Non-Cash Cumulative.

‘‘ NRSRO ’’ means a nationally recognized statistical rating organization within the meaning of Rule 15c3-1(c)(2)(vi)(F) under the Securities Exchange Act.

‘‘ Optional Deferral Provision ’’ means, with respect to any securities of the Company, a provision in the terms thereof or of the related transaction agreements that permits the Company to, in its sole discretion, defer in whole or in part payment of Distributions on such securities for up to ten years, without any remedy other than Permitted Remedies.

‘‘ Ordinary Shares ’’ means ordinary shares of the Company, par value 0.15144558 cents per share (including ordinary shares and rights to acquire ordinary shares issued pursuant to the Company’s employee benefit plans and any dividend reinvestment plan).

‘‘ Permitted Remedies ’’ means, with respect to any securities of the Company, one or more of the following remedies:

(a) rights in favor of the holders of such securities permitting such holders to elect or appoint one or more directors of the Company (including any such rights required by the listing requirements of any stock or securities exchange on which such securities may be listed or traded);

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(b) complete or partial prohibitions on the Company paying Distributions on or repurchasing ordinary shares or other securities that rank pari passu with or junior as to Distributions to such securities for so long as Distributions on such securities, including unpaid Distributions, remain unpaid; and

(c) provisions obliging the Company to cause, or use commercially reasonable efforts to cause, such unpaid Distributions to be paid in full pursuant to an Alternative Payment Mechanism.

‘‘ Person ’’ means any individual, corporation, partnership, joint venture, trust, limited liability company or corporation, unincorporated organization or government or any agency or political subdivision thereof.

‘‘ Preference Shares ’’ has the meaning specified in Recital A.

‘‘ Qualifying Preference Shares ’’ means Non-Cumulative perpetual preference shares of the Company (or depositary shares representing interests in such preference shares) that:

(a) ranks pari passu with or junior to other preference shares of the Company; and

(b) (i) is non-callable, (ii) is subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant or (iii) has Intent-Based Replacement Disclosure and a Mandatory Deferral Provision.

‘‘ Qualifying Replacement Capital Securities ’’ means securities that, in the determination of the Company’s board of directors reasonably construing the definitions and other terms of this Replacement Capital Covenant, satisfy one of the following criteria:

(a) Ordinary Shares;

(b) Debt Exchangeable for Equity;

(c) Mandatorily Convertible Preference Shares; or

(d) preference shares and debt securities that meet one of the following criteria:

(i) in connection with any redemption or repurchase of the Preference Shares prior to November 15, 2016, all preference shares or Most Junior Subordinated Debt Securities issued by the Company that meet one of the following criteria:

(A) (1) have no maturity or a maturity of at least 60 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (2) are Non-Cumulative;

(B) (1) have no maturity or a maturity of at least 60 years with Intent-Based Replacement Disclosure and (2) have a Mandatory Trigger Provision and an Optional Deferral Provision; or

(C) (1) have no maturity or a maturity at least 40 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (2) have a Mandatory Trigger Provision and an Optional Deferral Provision; or

(ii) in connection with any redemption or repurchase of the Preference Shares on or after November 15, 2016 and prior to November 15, 2036:

(A) all preference shares or debt securities described under clause (d)(i) of this definition;

(B) all preference shares or Most Junior Subordinated Debt Securities issued by the Company that meet one of the following criteria:

(1) (a) have no maturity or a maturity of at least 60 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) have an Optional Deferral Provision;

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(2) (a) have no maturity or a maturity of at least 60 years with Intent-Based Replacement Disclosure and (b) are Non-Cumulative;

(3) (a) have no maturity or a maturity of at least 60 years and (b) have a Mandatory Trigger Provision and an Optional Deferral Provision;

(4) (a) have a maturity at least 40 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) are Non-Cumulative;

(5) (a) have a maturity at least 40 years with Intent-Based Replacement Disclosure and (b) have a Mandatory Trigger Provision and an Optional Deferral Provision; or

(6) (a) have a maturity of at least 25 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) have a Mandatory Trigger Provision and an Optional Deferral Provision; or

(iii) in connection with any redemption or repurchase of Preference Shares at any time on or after November 15, 2036:

(A) all preference shares or debt securities described under clause (d)(i) or (d)(ii) of this definition;

(B) all preference shares or Most Junior Subordinated Debt Securities issued by the Company that meet one of the following criteria:

(1) (a) have no maturity or a maturity of at least 60 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) have an Optional Deferral Provision;

(2) (a) have no maturity or a maturity of at least 60 years with Intent-Based Replacement Disclosure and (b) have an Optional Deferral Provision;

(3) (a) have no maturity or a maturity of at least 60 years and (b) are Non-Cumulative;

(4) (a) have a maturity of at least 40 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) have an Optional Deferral Provision;

(5) (a) have a maturity at least 40 years with Intent-Based Replacement Disclosure and (b) are Non-Cumulative;

(6) (a) have a maturity of at least 40 years with Intent-Based Replacement Disclosure and (b) have a Mandatory Trigger Provision;

(7)(a) have a maturity of at least 25 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) are Non-Cumulative; or

(8) (a) have a maturity at least 25 years and are subject to a replacement capital covenant substantially similar to this Replacement Capital Covenant and (b) have a Mandatory Trigger Provision.

‘‘ Redesignation Date ’’ means, as to the Covered Debt in effect at any time, the earliest of:

(a) the date that is two years prior to the final maturity date of such Covered Debt;

(b) if the Company elects to redeem, or the Company or a Subsidiary of the Company elects to repurchase, such Covered Debt either in whole or in part with the consequence that after giving effect to such redemption or repurchase, the outstanding principal amount of such Covered Debt is less than $100,000,000, the applicable redemption or repurchase date; and

(c) if such Covered Debt is not Eligible Subordinated Debt, the date on which the Company issues Eligible Subordinated Debt.

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‘‘ Replacement Capital Covenant ’’ has the meaning specified in the introduction to this instrument.

‘‘ Securities Exchange Act ’’ means the United States Securities Exchange Act of 1934, as amended.

‘‘ Subsidiary ’’ means, at any time, any Person the shares of stock or other ownership interests of which having ordinary voting power to elect a majority of the board of directors or other managers of such Person are at the time owned, or the management or policies of which are otherwise at the time controlled, directly or indirectly through one or more intermediaries (including other Subsidiaries) or both, by another Person.

‘‘ Termination Date ’’ has the meaning specified in Section 4(a).

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