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UNDERWRITING AGREEMENT

Underwriting Agreement

UNDERWRITING AGREEMENT | Document Parties: ASPEN INSURANCE HOLDINGS LTD | LEHMAN BROTHERS INC. | UBS SECURITIES LLC You are currently viewing:
This Underwriting Agreement involves

ASPEN INSURANCE HOLDINGS LTD | LEHMAN BROTHERS INC. | UBS SECURITIES LLC

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Title: UNDERWRITING AGREEMENT
Governing Law: New York     Date: 11/15/2006
Industry: Insurance (Prop. and Casualty)    

UNDERWRITING AGREEMENT, Parties: aspen insurance holdings ltd , lehman brothers inc. , ubs securities llc
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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 ’’) appl


 
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