Aspen Insurance Holdings Ltd Contracts & Agreements

Management Consulting Agreement, dated March 28, 2019, between Aspen Insurance Holdings Limited and Apollo Management Holdings, L.P (Filed With SEC on March 29, 2019)

Settlement Agreement, dated March 28, 2019, by and among Aspen Insurance UK Services Limited, Aspen Insurance Holdings Limited and Mr. Christopher OKane (Filed With SEC on March 29, 2019)

Transaction Bonus Letter, dated as of February 15, 2019, by and between the Company and Scott Kirk (Filed With SEC on February 19, 2019)

Letter, dated August 29, 2018, between Thomas Lillelund and Aspen Insurance UK Services Limited (Filed With SEC on August 31, 2018)

Agreement and Plan of Merger, dated as of August 27, 2018, by and among Aspen Insurance Holdings Limited, Highlands Holdings, Ltd. and Highlands Merger Sub, Ltd (Filed With SEC on August 28, 2018)

Retention Letter between Scott Kirk and Aspen Insurance Holdings Limited, dated August 13, 2018 (Filed With SEC on August 14, 2018)

Settlement Agreement between Stephen Postlewhite and Aspen U.K. Services, dated May 9, 2018 (Filed With SEC on July 5, 2018)

Novation Agreement, dated June 29, 2018, between Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services, Inc., Aspen Bermuda Limited, Genpact International, Inc. and... (Filed With SEC on July 5, 2018)

Deed of Amendment between Aspen Bermuda Limited and Citibank Europe plc, dated as of June 29, 2018 (Filed With SEC on July 3, 2018)

International Assignment Letter, executed on June 6, 2018, between Mr. Christopher OKane and Aspen Insurance Holdings Limited (Filed With SEC on June 8, 2018)

Settlement Agreement between Stephen Postlewhite and Aspen U.K. Services, dated May 9, 2018 (Filed With SEC on May 11, 2018)

Separation Agreement between Brian Boornazian and Aspen U.S. Services, dated March 28, 2018 (Filed With SEC on March 29, 2018)

Addendum to a Change of Control Employment Agreement, dated March 15, 2018, between Charles Christopher OKane, Aspen Insurance UK Services Limited and the Company (Filed With SEC on March 19, 2018)

Addendum to a Change of Control Employment Agreement, dated March 15, 2018, between Scott Kirk, Aspen Insurance UK Services Limited and the Company (Filed With SEC on March 19, 2018)

Form of 2017 Performance Share Award Agreement, filed with this report (Filed With SEC on February 22, 2018)

Form of Restricted Share Unit Award Agreement made as part of the annual incentive grant (U.K. recipients), filed with this report (Filed With SEC on February 22, 2018)

Form of Restricted Share Unit Award Agreement made as part of the annual incentive grant (U.S. recipients), filed with this report (Filed With SEC on February 22, 2018)

ASPEN INSURANCE UK SERVICES LIMITED TERMS AND CONDITIONS OF EMPLOYMENT (Filed With SEC on February 22, 2017)

THOMAS LILLELUND AND ASPENINSURANCE UK SERVICES LIMITED SERVICE AGREEMENT TABLE OF CONTENTS (Filed With SEC on February 22, 2017)

Exhibit A (Filed With SEC on February 22, 2017)

Form of Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY (Filed With SEC on September 21, 2016)

ASPEN INSURANCE HOLDINGS LIMITED 9,000,000 Shares 5.625% Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25 Per Share) UNDERWRITING AGREEMENT (Filed With SEC on September 14, 2016)

ASPEN INSURANCE HOLDINGS LIMITED 2016 STOCK INCENTIVE PLAN FOR NON-EMPLOYEE DIRECTORS (Filed With SEC on August 4, 2016)

ASPEN INSURANCE HOLDINGS LIMITED LTIP PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on April 28, 2016)

ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on April 28, 2016)

ASPEN INSURANCE HOLDINGS LIMITED LTIP RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on April 28, 2016)

STEPHEN POSTLEWHITE AND ASPEN INSURANCE UK SERVICES LIMITED ________________________________________________ SERVICE AGREEMENT ________________________________________________... (Filed With SEC on February 19, 2016)

CHANGE OF CONTROL EMPLOYMENT AGREEMENT (Filed With SEC on February 19, 2016)

EMPLOYMENT AGREEMENT (Filed With SEC on February 19, 2016)

CHANGE OF CONTROL EMPLOYMENT AGREEMENT (Filed With SEC on February 19, 2016)

SCHEDULE Restrictive Covenants (Filed With SEC on November 12, 2015)

ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on April 30, 2015)

CHANGE OF CONTROL EMPLOYMENT AGREEMENT (Filed With SEC on February 23, 2015)

SCOTT KIRK AND ASPEN INSURANCE UK SERVICES LIMITED SERVICE AGREEMENT (Filed With SEC on February 23, 2015)

CHANGE OF CONTROL EMPLOYMENT AGREEMENT (Filed With SEC on February 23, 2015)

AMENDED AND RESTATED PLEDGE AGREEMENT (Filed With SEC on December 18, 2014)

FIRST AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT (Filed With SEC on December 15, 2014)

DATED 22 July 2014 RULES OF THE ASPEN INSURANCE HOLDINGS LIMITED AMENDED 2008 SHARESAVE SCHEME TABLE OF CONTENTS (Filed With SEC on November 7, 2014)

ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN AMENDED AND RESTATED EFFECTIVE AUGUST 1, 2014 (Filed With SEC on November 7, 2014)

AMENDMENT AGREEMENT (Amendment) dated as of October 28, 2014 between Charles Christopher OKane and Aspen Insurance UK Services Limited (AIUKSL) Aspen Insurance Holdings Limited... (Filed With SEC on October 31, 2014)

DATED OCTOBER 20, 2014 ASPEN BERMUDA LIMITED (1) and JAMES RICHARD FEW (2) ____________________________________________________ SEVERANCE AGREEMENT... (Filed With SEC on October 21, 2014)

ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on August 5, 2014)

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ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN (Filed With SEC on May 1, 2014)

ASPEN INSURANCE HOLDINGS LIMITED and COMPUTERSHARE INC., as Rights Agent RIGHTS AGREEMENT Dated as of April 17, 2014 TABLE OF CONTENTS (Filed With SEC on April 17, 2014)

ASPEN INSURANCE HOLDINGS LIMITED 2013 SHARE INCENTIVE PLAN (Filed With SEC on February 20, 2014)

THIRD SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER AND DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE Dated as of November 13, 2013... (Filed With SEC on November 13, 2013)

ASPEN INSURANCE HOLDINGS LIMITED $300,000,000 4.650% Senior Notes due 2023 UNDERWRITING AGREEMENT (Filed With SEC on November 7, 2013)

AMENDED AND RESTATED CREDIT AGREEMENT among ASPENINSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time... (Filed With SEC on June 13, 2013)

5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OFSECURITY (Filed With SEC on May 2, 2013)

ASPENINSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on April 29, 2013)

SUPPLEMENTAL CONFIRMATION (Filed With SEC on April 29, 2013)

ASPEN INSURANCE HOLDINGS LIMITED 11,000,000 Shares 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25 Per Share) UNDERWRITING... (Filed With SEC on April 29, 2013)

JULIAN MICHAEL CUSACK AND ASPEN INSURANCE UK SERVICES LIMITED AMENDED ANDRESTATED SERVICE AGREEMENT TABLE OF CONTENTS (Filed With SEC on February 26, 2013)

ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on February 26, 2013)

ASPEN INSURANCE U.S. SERVICES, INC. DEFERRED COMPENSATION PLAN Effective January 1, 2012 ASPEN INSURANCE U.S. SERVICES, INC. DEFERRED COMPENSATION PLAN ARTICLE I - PURPOSE;... (Filed With SEC on February 26, 2013)

JOHN WORTH AND ASPEN INSURANCE UK SERVICES LIMITED SERVICEAGREEMENT - i - TABLE OF CONTENTS (Filed With SEC on September 11, 2012)

ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on May 7, 2012)

ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on May 7, 2012)

7.250% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY (Filed With SEC on April 11, 2012)

ASPEN INSURANCE HOLDINGS LIMITED 6,000,000 Shares 7.25% Perpetual Non-Cumulative Preference Shares (Liquidation Preference$25 Per Share) UNDERWRITING AGREEMENT (Filed With SEC on April 10, 2012)

EX-101 INSTANCE DOCUMENT (Filed With SEC on February 28, 2012)

EX-101 INSTANCE DOCUMENT (Filed With SEC on November 7, 2011)

Entry into a Material Definitive Agreement (Filed With SEC on August 15, 2011)

FIRST AMENDMENT AGREEMENT (Filed With SEC on March 1, 2011)

EX-101 INSTANCE DOCUMENT (Filed With SEC on February 25, 2011)

Underwriting Agreement, dated December 7, 2010, among the Company, Citigroup Global Markets Inc. and Deutsche Bank Securities Inc., as representatives of the underwriters named... (Filed With SEC on December 10, 2010)

$280,000,000 (Filed With SEC on August 4, 2010)

the possibility of greater frequency or severity of claims and loss activity, including as a result of natural or man-made (including economic and political risks) catastrophic or... (Filed With SEC on February 26, 2010)

$200,000,000 Facility Agreement between Aspen Insurance Limited, Aspen Insurance UK Limited and Barclays Bank plc, dated October 6, 2009 (Filed With SEC on October 7, 2009)

Unaudited Condensed Consolidated Financial Statements (Filed With SEC on August 4, 2009)

Yours faithfully /s/ Siva Savaratnam For and on behalf of Citibank Europe plc Accepted and agreed on /s/ Julian Cusack For and on behalf of Aspen Insurance Limited Accepted and... (Filed With SEC on May 4, 2009)

Underwriting Agreement, dated March 31, 2009 among the Company and Deutsche Bank Securities Inc (Filed With SEC on April 1, 2009)

the continuing and uncertain impact of the current depressed credit environment, the banking crises and economic recessions in many of the countries in which we operate and of the... (Filed With SEC on February 26, 2009)

AMENDMENT TO THE ASPEN INSURANCE HOLDINGS LIMITED AMENDED 2003 SHARE INCENTIVE PLAN (Filed With SEC on November 10, 2008)

AMENDMENT TO THE ASPEN INSURANCE HOLDINGS LIMITED 2006 STOCK INCENTIVE PLAN FOR NON-EMPLOYEE DIRECTORS (Filed With SEC on November 10, 2008)

AMENDMENT TO THE 2006 PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on November 10, 2008)

AMENDMENT TO THE 2007 PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on November 10, 2008)

AMENDMENT TO THE RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on November 10, 2008)

Exhibit No (Filed With SEC on November 4, 2008)

AMENDMENT TO THE EMPLOYMENT AGREEMENT (Filed With SEC on November 3, 2008)

Fixed income maturities available for sale, at fair value (amortized cost $4,637.0 and $4,344.1) (Filed With SEC on August 6, 2008)

2,010,487 ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENT (Filed With SEC on May 14, 2008)

SHARE PURCHASE AGREEMENT (Filed With SEC on May 14, 2008)

ASPEN INSURANCE HOLDINGS LIMITED 2008 EMPLOYEE SHARE PURCHASE PLAN (Filed With SEC on May 5, 2008)

ASPEN INSURANCE HOLDINGS LIMITED 2008 SHARESAVE SCHEME DATED 2008 RULES OF THE ASPEN Insurance Holdings Limited 2008 Sharesave Scheme 1 TABLE OF CONTENTS (Filed With SEC on May 5, 2008)

ADDENDUM TO BOORNAZIAN CONTRACT (Filed With SEC on February 29, 2008)

ASPEN INSURANCE HOLDINGS LIMITED AMENDED 2003 SHARE INCENTIVE PLAN (Filed With SEC on February 29, 2008)

SUPPLEMENTAL CONFIRMATION (Filed With SEC on February 29, 2008)

LETTER AGREEMENT (Filed With SEC on February 29, 2008)

To:Aspen Insurance Holdings Limited Maxwell Roberts Building 1 Church Street Hamilton, HM 11 BermudaA/C:028569176From:Goldman, Sachs & Co.Re:Collared Accelerated Stock BuybackRef.... (Filed With SEC on November 8, 2007)

SCHEDULE A SUPPLEMENTAL CONFIRMATION (Filed With SEC on November 8, 2007)

RE: Amended Statement of Employment — Housing Allowance (Filed With SEC on November 5, 2007)

ASPEN INSURANCE HOLDINGS LIMITED NONQUALIFIED SHARE OPTION AGREEMENT (Filed With SEC on August 7, 2007)

ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT (Filed With SEC on August 7, 2007)

7,927,293 ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENT (Filed With SEC on July 2, 2007)

ASPEN INSURANCE HOLDINGS LIMITED 2006 STOCK INCENTIVE PLAN FOR NON-EMPLOYEE DIRECTORS (As Amended Effective March 21, 2007) (Filed With SEC on May 9, 2007)

ASPEN INSURANCE HOLDINGS LIMITED NON-EMPLOYEE DIRECTOR RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on May 9, 2007)

FIRST AMENDMENT TO SHAREHOLDER’S AGREEMENT (Filed With SEC on May 9, 2007)

ASPEN INSURANCE HOLDINGS LIMITED 2006 STOCK INCENTIVE PLAN FOR NON-EMPLOYEE DIRECTORS (As Amended Effective March 21, 2007) (Filed With SEC on May 7, 2007)

ASPEN INSURANCE HOLDINGS LIMITED NON-EMPLOYEE DIRECTOR RESTRICTED SHARE UNIT AWARD AGREEMENT (Filed With SEC on May 7, 2007)

FIRST AMENDMENT TO SHAREHOLDER’S AGREEMENT (Filed With SEC on May 7, 2007)

RICHARD DAVID HOUGHTON AND ASPEN INSURANCE UK SERVICES LIMITED SERVICE AGREEMENT (Filed With SEC on April 9, 2007)

7,927,288 ASPEN INSURANCE HOLDINGSLIMITED Ordinary Shares UNDERWRITING AGREEMENT (Filed With SEC on February 27, 2007)

To:AspenInsurance Holdings Limited Maxwell Roberts Building 1 ChurchStreet Hamilton, HM 11 BermudaA/C:028569176From:Goldman,Sachs & Co.Re:Collared AcceleratedStock BuybackRef.... (Filed With SEC on February 22, 2007)

SUPPLEMENTALCONFIRMATION (Filed With SEC on February 22, 2007)

SCHEDULE B TRADENOTIFICATION (Filed With SEC on February 22, 2007)

SHARE PURCHASE AGREEMENT (Filed With SEC on December 6, 2006)

8,000,000 Shares ASPEN INSURANCE HOLDINGSLIMITED 7.401% Perpetual Non-Cumulative PreferenceShares (Liquidation Preference $25 PerShare) UNDERWRITINGAGREEMENT (Filed With SEC on November 15, 2006)

CERTIFICATE OFDESIGNATION OF PERPETUAL NON-CUMULATIVE PREFERENCESHARES OF ASPEN INSURANCE HOLDINGS LIMITED (Filed With SEC on November 15, 2006)

JULIANMICHAEL CUSACK AND ASPEN INSURANCEHOLDINGSLIMITED AMENDEDAND RESTATED SERVICEAGREEMENT (Filed With SEC on November 3, 2006)

Committed letter of credit facility (Filed With SEC on October 13, 2006)

Insurance Letters of Credit − Master Agreement Insurance/Reinsurance Companies or Brokers (Filed With SEC on October 13, 2006)

PLEDGE AGREEMENT (Filed With SEC on October 13, 2006)

Citibank,N.A. is incorporated with limited liability under the National Bank Actof the U.S.A. and has its head office at 399 Park Avenue, New York, NY10043, U.S.A.. Citibank, N.A.... (Filed With SEC on October 13, 2006)

ASSIGNMENT AGREEMENT (THIS‘‘AGREEMENT’’) October 11, 2006 (Filed With SEC on October 13, 2006)

ANNEX ONE REINSURANCEDEPOSIT AGREEMENT (CHARGE FORM – CITIBANK, N.A. AS CUSTODIAN)(FORM 12) SCHEDULE TWO (Filed With SEC on October 13, 2006)

COMMITMENT INCREASE SUPPLEMENT (Filed With SEC on September 1, 2006)

STUARTW SINCLAIR AND ASPEN INSURANCE UKSERVICESLIMITED SERVICEAGREEMENT (Filed With SEC on August 10, 2006)

ASPEN INSURANCE HOLDINGS LIMITED 2006 STOCK OPTIONPLAN FOR NON-EMPLOYEE DIRECTORS (Filed With SEC on May 26, 2006)

ASPEN INSURANCE HOLDINGS LIMITED NON-EMPLOYEEDIRECTOR NONQUALIFIED SHARE OPTION AGREEMENT (Filed With SEC on May 26, 2006)

(1)SARAH ANNDAVIES AND (2)ASPEN INSURANCE UK SERVICES LIMITED (3)ASPEN INSURANCE HOLDINGSLIMITED SERVICEAGREEMENT (Filed With SEC on May 22, 2006)

DATED 19 May2006 ASPEN INSURANCE UK SERVICES LIMITED (1) ASPENINSURANCE HOLDINGS LIMITED(2) and SARAH ANN DAVIES(3) COMPROMISEAGREEMENT LeBoeuf,Lamb, Greene & MacRae 1 Minster... (Filed With SEC on May 22, 2006)

AMENDMENT (Filed With SEC on April 18, 2006)

WELLINGTON RE SERVICES LIMITED TERMS ANDCONDITIONS OF EMPLOYMENT (Filed With SEC on March 6, 2006)

EMPLOYMENT AGREEMENT (Filed With SEC on March 6, 2006)

ASPEN INSURANCE HOLDINGS LIMITED NONQUALIFIEDSHARE OPTION AGREEMENT (Filed With SEC on March 6, 2006)

ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCESHARE AWARD AGREEMENT (Filed With SEC on March 6, 2006)

4,000,000 PerpetualPIERSSM* ASPEN INSURANCE HOLDINGS LIMITED 5.625%Perpetual Preferred Income Equity Replacement Securities (PerpetualPIERS) ($50 Liquidation Preference)... (Filed With SEC on December 13, 2005)

14,333,333 ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENT (Filed With SEC on December 13, 2005)

CERTIFICATE OF DESIGNATION OF 5.625% PERPETUAL PREFERRED INCOME EQUITY REPLACEMENTSECURITIES (PERPETUAL PIERS) OF ASPEN INSURANCE HOLDINGS LIMITED (Filed With SEC on December 13, 2005)

CERTIFICATE OFDESIGNATION OF PERPETUAL PREFERENCESHARES OF ASPEN INSURANCE HOLDINGSLIMITED (Filed With SEC on December 13, 2005)

17,551,558 ASPEN INSURANCEHOLDINGS LIMITED Ordinary Shares UNDERWRITINGAGREEMENT (Filed With SEC on October 7, 2005)

ASPEN INSURANCE HOLDINGS LIMITED AMENDED AND RESTATED INSTRUMENT CONSTITUTING OPTIONS TO SUBSCRIBE FOR SHARES IN ASPEN INSURANCE HOLDINGS LIMITED 1 (Filed With SEC on September 30, 2005)

$400,000,000 5-YEAR CREDIT AGREEMENT among ASPENINSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Timeto Time Parties Hereto, The Several Lenders from Time to TimeParties... (Filed With SEC on August 4, 2005)

EMPLOYMENT AGREEMENT (Filed With SEC on March 26, 2004)

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Aspen Insurance Holdings Ltd Contracts & Agreements