WHITE MOUNTAINS INSURANCE GROUP LTD Contracts & Agreements

Securities Purchase Agreement dated May 9, 2022 by and among Riser Merger Sub, Inc., White Mountains Catskill Holdings (Luxembourg) S. r. l., NSM Insurance HoldCo, LLC and the... (Filed With SEC on May 10, 2022)

White Mountains Bonus Plan (Filed With SEC on May 6, 2022)

Loan and Security Agreement, dated as of March 31, 2022 among HG Global Ltd., Hudson Structured Capital Management Ltd. and the lenders from time to time party thereto (Filed With SEC on May 6, 2022)

Consulting Agreement, dated as of November 1, 2021, between White Mountains Capital LLC and Mr. Caffrey (Filed With SEC on December 2, 2021)

Paying Agency Agreement dated 13 July 2021 between Group Ark Insurance Limited, The Bank of New York Mellon, London Branch and The Bank of New York Mellon SA/NV, Dublin Branch (Filed With SEC on November 8, 2021)

Paying Agency Agreement dated 11 August 2021 between Group Ark Insurance Limited, The Bank of New York Mellon, London Branch and The Bank of New York Mellon SA/NV, Dublin Branch (Filed With SEC on November 8, 2021)

Paying Agency Agreement dated 8 September 2021 between Group Ark Insurance Limited, The Bank of New York Mellon, London Branch and The Bank of New York Mellon SA/NV, Dublin Branch (Filed With SEC on November 8, 2021)

Employment Agreement and Release between White Mountains Capital LLC and J. Brian Palmer dated February 25, 2021 (Filed With SEC on February 26, 2021)

Employment Agreement between White Mountains Capital LLC and Frank R. Bazos dated December 16, 2020 (Filed With SEC on February 26, 2021)

Subscription and Purchase Agreement amended and restated on December 14, 2020 by and among Ark Insurance Holdings Limited, Bridge Holdings (Bermuda) Ltd., White Mountains... (Filed With SEC on December 15, 2020)

Subscription and Purchase Agreement dated October 1, 2020 by and among Ark Insurance Holdings Limited, Bridge Holdings (Filed With SEC on October 1, 2020)

Management Warranty Deed dated (Filed With SEC on October 1, 2020)

White Mountains Bonus Plan (Filed With SEC on May 6, 2019)

FIRST AMENDMENT dated as of December 3, 2018, among NSM INSURANCE GROUP, LLC, a Delaware limited liability company, NSM INSURANCE HOLDCO, LLC, a Delaware limited liability... (Filed With SEC on May 6, 2019)

SECOND AMENDMENT dated as of April 1, 2019, among NSM INSURANCE GROUP, LLC, a Delaware limited liability company, NSM INSURANCE HOLDCO, LLC, a Delaware limited liability company,... (Filed With SEC on May 6, 2019)

Second Amended and Restated Supplemental Trust Agreement by and among Build America Mutual Assurance Company, HG Re Ltd. and The Bank of New York Mellon, dated December 4, 2018 (Filed With SEC on February 27, 2019)

Second Amended and Restated Investment Management Agreement, dated as of September 28, 2017, by and between White Mountains Advisors LLC and OneBeacon Insurance Group, Ltd (Filed With SEC on September 28, 2017)

Employment Agreement dated May 2, 2017 between White Mountains Insurance Group, Ltd. and David T. Foy (Filed With SEC on August 4, 2017)

Retirement Agreement dated March 1, 2017 between White Mountains Insurance Group, Ltd. and Raymond Barrette (Filed With SEC on May 2, 2017)

Fourth Amendment dated as of February 28, 2017 to the Amended and Restated Investment Management Agreement dated as of December 23, 2014 by and between White Mountains Advisors... (Filed With SEC on May 2, 2017)

OneBeacon's 2017 Management Incentive Plan (Filed With SEC on May 2, 2017)

OneBeacon 2017 Long-Term Incentive Plan (Filed With SEC on May 2, 2017)

Form of OneBeacon Insurance Group, Ltd. 2017 Special Restricted Share Award Agreement (Filed With SEC on May 2, 2017)

Form of OneBeacon Insurance Group, Ltd. 2017-2019 Restricted Share Award Agreement (Filed With SEC on May 2, 2017)

VOTING AGREEMENT (Filed With SEC on May 2, 2017)

ONEBEACONS 2016 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 27, 2017)

SELLER PRIORITY SURPLUS NOTE Number 1 (Filed With SEC on February 27, 2017)

SELLER PARI PASSU SURPLUS NOTE Number 1 (Filed With SEC on February 27, 2017)

SECOND AMENDMENT TO THE AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on May 2, 2016)

THIRD AMENDMENT TO THE AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on May 2, 2016)

ONEBEACONS 2016 MANAGEMENT INCENTIVE PLAN (Filed With SEC on May 2, 2016)

WHITE MOUNTAINS ANNUAL BONUS PROGRAM (Filed With SEC on February 29, 2016)

ONEBEACONS 2015 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 29, 2016)

EMPLOYMENT AGREEMENT (Filed With SEC on November 2, 2015)

SABBATICAL AGREEMENT (Filed With SEC on August 3, 2015)

STOCK PURCHASE AGREEMENT Among LONE TREE HOLDINGS LTD., SIRIUS INTERNATIONAL INSURANCE GROUP, LTD., CM INTERNATIONAL HOLDING PTE. LTD. and CM BERMUDA LIMITED Dated as of July 24,... (Filed With SEC on July 27, 2015)

AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 27, 2015)

PROSPECTOR PARTNERS AND ONEBEACON INSURANCE GROUP, LTD. AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 27, 2015)

ONEBEACONS 2014 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 27, 2015)

AMENDMENT NO. 1 TO STOCK PURCHASE AGREEMENT (Filed With SEC on February 27, 2015)

AMENDMENT NO. 4 TO STOCK PURCHASE AGREEMENT (Filed With SEC on February 27, 2015)

AMENDMENT NO.1 TO CREDIT AGREEMENT (Filed With SEC on October 29, 2014)

AMENDMENT NO. 3 TO STOCK PURCHASE AGREEMENT (Filed With SEC on July 29, 2014)

AMENDED AND RESTATED SURPLUS NOTE PURCHASE AGREEMENT Between BUILD AMERICA MUTUAL ASSURANCE COMPANY, as Issuer and HG HOLDINGS LTD. and HG RE LTD. as Purchasers Dated as of... (Filed With SEC on April 28, 2014)

Page 2 (Filed With SEC on February 28, 2014)

AMENDMENT TO STOCK PURCHASE AGREEMENT (Filed With SEC on February 28, 2014)

CREDIT AGREEMENT Dated as of August 14, 2013 among WHITE MOUNTAINS INSURANCE GROUP, LTD., as the Borrower, WELLS FARGO BANK, NATIONAL ASSOCIATION, as Administrative Agent, Swing... (Filed With SEC on October 28, 2013)

$275,000,000 OneBeacon U.S. Holdings, Inc. 4.60% Senior Notes due 2022 Guaranteed by OneBeacon Insurance Group, Ltd. UNDERWRITING AGREEMENT (Filed With SEC on March 1, 2013)

ONEBEACON U.S. HOLDINGS, INC. ONEBEACON INSURANCE GROUP, LTD. and THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. Trustee SENIOR INDENTURE Dated as of November 9, 2012 Providing... (Filed With SEC on March 1, 2013)

ONEBEACON U.S. HOLDINGS, INC. AND THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. as Trustee AND ONEBEACON INSURANCE GROUP, LTD. as Guarantor FIRST SUPPLEMENTAL INDENTURE to the... (Filed With SEC on March 1, 2013)

OneBeacon Deferred Compensation Plan (Filed With SEC on March 1, 2013)

ONEBEACONS 2012 MANAGEMENT INCENTIVE PLAN (Filed With SEC on March 1, 2013)

STOCK PURCHASE AGREEMENT BY AND AMONG ONEBEACON INSURANCE GROUP LLC, ONEBEACON INSURANCE GROUP, LTD., TREBUCHET US HOLDINGS, INC. AND ARMOUR GROUP HOLDINGS LIMITED DATED AS OF... (Filed With SEC on October 30, 2012)

REGULATION 114 TRUST AGREEMENT (Filed With SEC on October 30, 2012)

SUPPLEMENTAL TRUST AGREEMENT (Filed With SEC on October 30, 2012)

SURPLUS NOTE PURCHASE AGREEMENT Between BUILD AMERICA MUTUAL ASSURANCE COMPANY, as Issuer and HG HOLDINGS LTD. and HG RE LTD. as Purchasers Dated as of July 17, 2012 (Filed With SEC on October 30, 2012)

INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 28, 2012)

FIRST AMENDMENT TO INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 28, 2012)

PROSPECTOR PARTNERS, LLC INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 28, 2012)

1. PROSPECTOR PARTNERS, LLC AMENDMENT NO. 1 TO INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 28, 2012)

ONEBEACONS 2011 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 28, 2012)

RESTRICTED SHARE AWARD AGREEMENT (Filed With SEC on February 28, 2012)

Esurance Holdings, Inc. Performance Unit Plan 2010-2012 (Filed With SEC on February 28, 2011)

ONEBEACONS 2010 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 28, 2011)

W IT N E S S E T H : (Filed With SEC on October 29, 2010)

Esurance Holdings, Inc. Performance Unit Plan 2007-2009 (Filed With SEC on February 26, 2010)

Esurance Holdings, Inc. Performance Unit Plan 2008-2010 (Filed With SEC on February 26, 2010)

Esurance Holdings, Inc. Performance Unit Plan 2009-2011 (Filed With SEC on February 26, 2010)

ESURANCE HOLDINGS, INC. SELECT DEFERRED COMPENSATION PLAN (Filed With SEC on February 26, 2010)

ESURANCE HOLDINGS, INC. AMENDED AND RESTATED TOP HAT DEFERRED COMPENSATION PLAN (Filed With SEC on February 26, 2010)

Esurance Holdings, Inc. Esurance Restricted Unit Plan (Filed With SEC on February 26, 2010)

First Amendment to the OneBeacon Long-Term Incentive Plan (2007) FIRST (Filed With SEC on February 26, 2010)

ONEBEACONS 2009 MANAGEMENT INCENTIVE PLAN (Filed With SEC on February 26, 2010)

SECOND AMENDMENT TO CREDIT AGREEMENT (Filed With SEC on February 27, 2009)

THIRD AMENDMENT TO CREDIT AGREEMENT (Filed With SEC on February 27, 2009)

FIRST AMENDMENT TO CREDIT AGREEMENT (Filed With SEC on August 1, 2008)

EXCHANGEAGREEMENT by andamong BERKSHIREHATHAWAY INC. GENERALREINSURANCE CORPORATION WHITEMOUNTAINS INSURANCE GROUP, LTD. and RAILSPLITTERHOLDINGS CORPORATION As ofMarch 8, 2008 (Filed With SEC on March 10, 2008)

TAXMATTERS AGREEMENT by andamong GENERALREINSURANCE CORPORATION BERKSHIREHATHAWAY INC. WHITEMOUNTAINS INSURANCE GROUP, LTD. and RAILSPLITTERHOLDINGS CORPORATION As ofMarch 8, 2008 (Filed With SEC on March 10, 2008)

CREDIT AGREEMENT Dated as of June 19, 2007 among WHITEMOUNTAINS INSURANCE GROUP, LTD., as the Borrower, BANK OFAMERICA, N.A., as AdministrativeAgent, Swing Line Lender and Issuing... (Filed With SEC on August 2, 2007)

FISCALAGENCY AGREEMENT between WHITEMOUNTAINS RE GROUP, LTD. asIssuer AND THEBANK OF NEW YORK asFiscal Agent 6.375%Senior Notes Due 2017 Dated as ofMarch 19, 2007 (Filed With SEC on March 19, 2007)

CREDIT AGREEMENT Dated as of November 14, 2006 among WHITE MOUNTAINS INSURANCE GROUP, LTD., and WHITE MOUNTAINS RE GROUP, LTD., as the Borrowers, BANK OF AMERICA, N.A., as... (Filed With SEC on February 28, 2007)

CREDITAGREEMENT Dated as ofNovember 14, 2006 among FUND AMERICAN COMPANIES, INC. as the Borrower, ONEBEACON INSURANCE GROUP, LTD., as Parent, BANK OFAMERICA, N.A., as... (Filed With SEC on February 28, 2007)

PROSPECTOR PARTNERS, LLC INVESTMENT MANAGEMENT AGREEMENT (Filed With SEC on February 28, 2007)

OneBeaconInsurance 2006Management Incentive Plan (Filed With SEC on February 28, 2007)

ONEBEACON INSURANCE GROUP, LTD. NON-QUALIFIED STOCK OPTION AGREEMENT (Filed With SEC on February 28, 2007)

ESURANCE HOLDINGS, INC. SELECT DEFERRED COMPENSATION PLAN (Filed With SEC on March 7, 2006)

ONEBEACONS 2005 MANAGEMENT INCENTIVE PLAN (Filed With SEC on March 7, 2006)

ONEBEACON PERFORMANCEPLAN (as Adopted by OneBeaconCorporation) (Filed With SEC on March 7, 2006)

SUMMARY OF THE WHITE MOUNTAINS INSURANCE GROU DEFERRED COMPENSATION PLAN (Filed With SEC on March 2, 2004)

FUND AMERICAN DEFERRED COMPENSATION PLAN ARTICLE I (Filed With SEC on March 2, 2004)

ONEBEACONPERFORMANCE UNIT PLAN (Filed With SEC on March 2, 2004)

ONEBEACON DEFERRED COMPENSATION PLAN ARTICLE I (Filed With SEC on March 2, 2004)

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WHITE MOUNTAINS INSURANCE GROUP LTD Contracts & Agreements