White Mountains Insurance Group, Ltd.

White Mountains Insurance Group, Ltd. – Execution Version CREDIT AGREEMENT Dated as of May 11, 2018 Among NSM INSURANCE GROUP, LLC, as the Borrower, NSM INSURANCE HOLDCO, LLC, as Holdings, ARES CAPITAL CORPORATION, as Administrative Agent, and THE LENDERS AND L/C ISSUERS PARTY HERETO FROM TIME TO TIME ARES CAPITAL MANAGEMENT LLC, as Sole Bookrunner and Sole Lead Arranger and LAKE FOREST BANK & TRUST COMPANY, N.A., as Documentation Agent [[NYCORP:3713047v14:05/10/2018--10:17 PM]] (August 7th, 2018)

White Mountains Insurance Group, Ltd. – Unit Purchase Agreement by and Among Nsm Acquisition Holdings, Llc, Aig Property Casualty U.S., Inc., the Management Sellers, White Mountains Insurance Group, Ltd., White Mountains Catskill Holdings, Inc., Nsm Insurance Holdco, Llc, and Abry Partners Viii, L.P., as Seller Representative Dated as of March 31, 2018 (May 2nd, 2018)

This UNIT PURCHASE AGREEMENT (this "Agreement"), dated as of March 31, 2018, is made by and among NSM Acquisition Holdings, LLC, a Delaware limited liability company ("NSM Holdings"), AIG Property Casualty U.S., Inc., a Delaware corporation ("AIG"), each Management Seller (as defined herein) (each of NSM Holdings, AIG and each Management Seller may be referred to herein from time to time as a "Seller", and collectively, the "Sellers"), NSM Insurance HoldCo, LLC, a Delaware limited liability company (the "Company"), White Mountains Catskill Holdings, Inc., a Delaware corporation ("Buyer"), White Mountains Insurance Group, Ltd., a Bermuda exempted limited liability company ("Parent"), and ABRY Partners VIII, L.P., a Delaware limited partnership, solely in its capacity as the Seller Representative (as defined in Section 11.9(a) hereto). The Company, the Sellers, Buyer and the Seller Representative shall be referred to herein from time to time collectively as the "Parties". Capitalized t

White Mountains Insurance Group, Ltd. – Second Amended and Restated Investment Management Agreement (September 28th, 2017)

WHITE MOUNTAINS ADVISORS LLC, a Delaware limited liability company (the "Advisor"), having an address at 200 Hubbard Road, Guilford, Connecticut 06437, and OneBeacon Insurance Group, Ltd., an exempted limited liability company organized under the laws of Bermuda (the "Client"), having an address at 605 North Highway 169, Plymouth, Minnesota 55441, and each affiliate company of the Client listed on Schedule B, and each having an address of 605 North Highway 169, Plymouth, Minnesota 55441, or which hereinafter becomes a party to this Agreement (each, an "Affiliated Company", and collectively, the "Affiliated Companies"), hereby enter into this Second Amended and Restated Investment Management Agreement (this "Agreement"), dated as of September 28, 2017, and hereby amend and restate in its entirety the Amended and Restated Investment Management Agreement, dated December 23, 2014. The parties hereby agree that the Advisor shall act as discretionary advisor with respect to certain assets of

White Mountains Insurance Group, Ltd. – Employment Agreement (August 4th, 2017)

THIS EMPLOYMENT AGREEMENT (this "Agreement"), dated as of May 2, 2017, is between White Mountains Insurance Group, Ltd., a Bermuda corporation (the "Company"), and David T. Foy (the "Executive").

White Mountains Insurance Group, Ltd. – OneBeacon Insurance Group, Ltd. Long-Term Incentive Plan 2017-2019 Restricted Share Award Agreement (May 2nd, 2017)

THIS AWARD AGREEMENT (this "Agreement") is made effective as of the 28th day of February 2017, between OneBeacon Insurance Group, Ltd., a Bermuda company (the "Company") and <First Name><Last Name> (the "Participant").

White Mountains Insurance Group, Ltd. – OneBeacon Insurance Group, Ltd. Long-Term Incentive Plan 2017 Special Restricted Share Award Agreement (May 2nd, 2017)

THIS AWARD AGREEMENT (this "Agreement") is made effective as of the 28th day of February 2017, between OneBeacon Insurance Group, Ltd., a Bermuda company (the "Company") and <First Name><Last Name> (the "Participant").

White Mountains Insurance Group, Ltd. – OneBeacon 2017 Long-Term Incentive Plan (May 2nd, 2017)

The purpose of this Plan is to advance the interests of OneBeacon Insurance Group, Ltd. (the "Company") and its shareholders by providing the ability to grant long-term incentives to certain key employees, consultants and directors of the Company and of its Subsidiaries.

White Mountains Insurance Group, Ltd. – Onebeacon's 2017 Management Incentive Plan (May 2nd, 2017)

The Management Incentive Plan (MIP) is an integral part of the total compensation program for managers and certain key individual contributors. Its primary purpose is to focus attention on 2017 profitability goals and to reward eligible participants for the achievement of those goals.

White Mountains Insurance Group, Ltd. – March 1, 2017 Raymond Barrette Dear Ray: (May 2nd, 2017)

This letter agreement (this "Agreement") is intended to set forth our mutual understanding and agreement regarding your retirement as Chief Executive Officer ("CEO") of White Mountains Insurance Group, Ltd. (the "Company") and as a member of the board of directors of the Company (the "Board").

White Mountains Insurance Group, Ltd. – Voting Agreement (May 2nd, 2017)

THIS VOTING AGREEMENT (this "Agreement"), dated as of May 2, 2017, among Intact Financial Corporation, a Canadian corporation ("Parent"), the Persons executing this Agreement as "Shareholders" on the signature page hereto (each a "Shareholder" and collectively, the "Shareholders"), and, solely for purposes of Section 5.11, White Mountains Insurance Group, Ltd. ("WTM"), a Bermuda exempted limited liability company.

White Mountains Insurance Group, Ltd. – Fourth Amendment to Amended and Restated Investment Management Agreement (May 2nd, 2017)

THIS FOURTH AMENDMENT dated as of February 28, 2017, to the Amended and Restated Investment Management Agreement (the "Agreement") dated as of December 23, 2014, is entered into between WHITE MOUNTAINS ADVISORS LLC, a limited liability company organized under the laws of the state of Delaware (the "Advisor") and ONEBEACON INSURANCE GROUP, LTD., an exempted limited liability company organized under the laws of Bermuda (the "Client").

White Mountains Insurance Group, Ltd. – Onebeacon's 2016 Management Incentive Plan (February 27th, 2017)

The Management Incentive Plan (MIP) is an integral part of the total compensation program for managers and certain key individual contributors. Its primary purpose is to focus attention on 2016 profitability goals and to reward eligible participants for the achievement of those goals.

White Mountains Insurance Group, Ltd. – Seller Priority Surplus Note (February 27th, 2017)

For Value Received, ONEBEACON INSURANCE COMPANY, a Pennsylvania domiciled, property and casualty insurance company located at OneBeacon Insurance Company, 3 Batterymarch Park, Quincy, MA 02169 (the "Company") promises to pay to OneBeacon Insurance Group LLC of 601 Carlson Parkway, Minnetonka, MN 55305 (the "Holder") the principal sum of $57,900,000 (the "Surplus Note"), and to pay interest thereon, from December 23, 2014 or from the most recent Scheduled Interest Payment Date (as defined below) for which interest has been paid or duly provided for, semi-annually in arrears on March 15 and August 31 in each year and on the date on which this Surplus Note matures, commencing March 15, 2015 (each, a "Scheduled Interest Payment Date"), at the applicable Stated Rate (as defined below), until the principal hereof is paid or duly provided for. The terms and conditions governing payment of this Surplus Note are as follows:

White Mountains Insurance Group, Ltd. – SELLER PARI PASSU SURPLUS NOTE Number 1 (February 27th, 2017)

For Value Received, ONEBEACON INSURANCE COMPANY, a Pennsylvania domiciled, property and casualty insurance company located at OneBeacon Insurance Company, 3 Batterymarch Park, Quincy, MA 02169 (the "Company") promises to pay to OneBeacon Insurance Group LLC of 601 Carlson Parkway, Minnetonka, MN 55305 (the "Holder") the principal sum of $43,100,000 (the "Surplus Note"), and to pay interest thereon, from December 23, 2014 or from the most recent Scheduled Interest Payment Date (as defined below) for which interest has been paid or duly provided for, semi-annually in arrears on March 15 and August 31 in each year and on the date on which this Surplus Note matures, commencing March 15, 2015 (each, a "Scheduled Interest Payment Date"), at the applicable Stated Rate (as defined below), until the principal hereof is paid or duly provided for. The terms and conditions governing payment of this Surplus Note are as follows:

White Mountains Insurance Group, Ltd. – Employment Agreement (November 2nd, 2015)

This Employment Agreement (this "Agreement") is dated as of July 24, 2015, between Sirius International Insurance Group, Ltd., a Bermuda corporation (the "Company"), and Allan L. Waters ("Executive"). All capitalized terms used but not defined herein shall have the meanings set forth in the Amended and Restated Sirius Group Long Term Incentive Plan as in effect on the date hereof (the "Sirius LTIP"), which is attached hereto as Exhibit A.

White Mountains Insurance Group, Ltd. – Sabbatical Agreement (August 3rd, 2015)

THIS SABBATICAL AGREEMENT (this "Agreement") dated June 1, 2015 is by and between White Mountains Capital, Inc., a Delaware corporation with principal executive offices at 80 South Main St., Hanover, NH 03755 (the "Company"), on behalf of itself, its ultimate parent White Mountains Insurance Group, Ltd., a Bermuda company ("WMIG"), and all other subsidiaries of WMIG (collectively with the Company, the "Company Group"), and G. Manning Rountree, an individual residing at 181 Acorn Hill Road in Lyme, New Hampshire (the "Executive").

White Mountains Insurance Group, Ltd. – 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, 2015 (July 27th, 2015)

STOCK PURCHASE AGREEMENT (this "Agreement"), dated as of July 24, 2015, among Lone Tree Holdings Ltd., an exempted company with limited liability incorporated under the laws of Bermuda with registered number 39337 having its registered office at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda ("Seller"), Sirius International Insurance Group, Ltd., an exempted company with limited liability incorporated under the laws of Bermuda with registered number 39821 having its registered office at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda (the "Company"), CM International Holding Pte. Ltd., a company with limited liability incorporated under the laws of Singapore with registered number 201437634R having its registered office at 20 Collyer Quay #23-01, Singapore 049319 ("Purchaser"), and CM Bermuda Limited, an exempted company with limited liability incorporated under the laws of Bermuda with registered number 50418 having its registered office at Canon's Court, 22 Victo

White Mountains Insurance Group, Ltd. – Amended and Restated Investment Management Agreement (February 27th, 2015)

WHITE MOUNTAINS ADVISORS LLC, a Delaware limited liability company (the "Advisor"), having an address at 200 Hubbard Road, Guilford, Connecticut 06437, and OneBeacon Insurance Group, Ltd. , an exempted limited liability company organized under the laws of Bermuda (the "Client"), having an address at 601 Carlson Parkway, Suite 600, Minnetonka, Minnesota 55305, and each affiliate company of the Client listed on Schedule B, and each having an address of 601 Carlson Parkway, Suite 600, Minnetonka, Minnesota 55305, or which hereinafter becomes a party to this Agreement (each, an "Affiliated Company", and collectively, the "Affiliated Companies"), hereby enter into this Investment Management Agreement (this "Agreement"), dated as of December 23, 2014, and hereby agree that the Advisor shall act as discretionary advisor with respect to certain assets of the Client and the Affiliated Companies described below (the "Investment Account") on the following terms and conditions:

White Mountains Insurance Group, Ltd. – Amendment No. 4 to Stock Purchase Agreement (February 27th, 2015)

This Amendment No. 4 (this "Amendment"), dated as of November 3, 2014, is made among OneBeacon Insurance Group LLC ("Seller"), Trebuchet US Holdings, Inc. ("Purchaser"), OneBeacon Insurance Group, Ltd. ("Seller Parent") and Armour Group Holdings Limited ("Purchaser Parent"). Capitalized terms used but not defined in this Amendment have the meanings set forth in the Agreement (as defined below).

White Mountains Insurance Group, Ltd. – Amendment No. 1 to Stock Purchase Agreement (February 27th, 2015)

This Amendment No. 1 (this "Amendment"), dated as of February 1, 2013, is made among OneBeacon Insurance Group LLC ("Seller"), Trebuchet US Holdings, Inc. ("Purchaser"), OneBeacon Insurance Group, Ltd. ("Seller Parent") and Armour Group Holdings Limited ("Purchaser Parent"). Capitalized terms used but not defined in this Amendment have the meanings set forth in the Agreement (as defined below).

White Mountains Insurance Group, Ltd. – OneBeacon Long-Term Incentive Plan (2007) (February 27th, 2015)

White Mountains Insurance Group, Ltd. – Prospector Partners and Onebeacon Insurance Group, Ltd. Amended and Restated Investment Management Agreement (February 27th, 2015)

PROSPECTOR PARTNERS, LLC, a Delaware limited liability company (the "Adviser"), having an address at 370 Church Street, Guilford, Connecticut 06437, and OneBeacon Insurance Group, Ltd., a Bermuda Corporation ("OneBeacon"), having an address at Bank of Butterfield Building, 42 Reid Street, Hamilton HM 12, Bermuda, hereby enter into this Amended and Restated Investment Management Agreement, dated as of February 25, 2015 (this "Agreement"), and hereby agree that the Adviser shall act as discretionary adviser with respect to the specified assets of each subsidiary of OneBeacon identified on Schedule A (each, a "Client") to this Agreement as such schedule may be amended from time to time to add new subsidiaries as Clients on the following terms and conditions:

White Mountains Insurance Group, Ltd. – Onebeacon's 2014 Management Incentive Plan (February 27th, 2015)

The Management Incentive Plan (MIP) is an integral part of the total compensation program for managers and certain senior key individual contributors. Its primary purpose is to focus attention on 2014 profitability goals and to reward eligible participants for the achievement of those goals.

White Mountains Insurance Group, Ltd. – Amendment No. 1 to Credit Agreement (October 29th, 2014)

This Amendment (this "Amendment") is entered into as of September 24, 2014 by and among White Mountains Insurance Group, Ltd., a company existing under the laws of Bermuda (the "Borrower"), Wells Fargo Bank, National Association, individually and as administrative agent (the "Administrative Agent"), and the other financial institutions signatory hereto.

White Mountains Insurance Group, Ltd. – Amendment No. 3 to Stock Purchase Agreement (July 29th, 2014)

This Amendment No. 3 (this "Amendment"), dated as of June 19, 2014, is made among OneBeacon Insurance Group LLC ("Seller"), Trebuchet US Holdings, Inc. ("Purchaser"), OneBeacon Insurance Group, Ltd. ("Seller Parent") and Armour Group Holdings Limited ("Purchaser Parent"). Capitalized terms used but not defined in this Amendment have the meanings set forth in the Agreement (as defined below).

White Mountains Insurance Group, Ltd. – AMENDED AND RESTATED SURPLUS NOTE PURCHASE AGREEMENT Between (April 28th, 2014)

This AMENDED AND RESTATED SURPLUS NOTE PURCHASE AGREEMENT, dated as of January 1, 2014, is made by and between Build America Mutual Assurance Company, a New York mutual insurance company (together with its successors and assigns, the "Company" or the "Issuer"), HG Holdings Ltd., an exempted Bermuda limited company (together with its successors and assigns, the "Series 2012-A Purchaser"), and HG Re Ltd., an exempted Bermuda limited company (together with its successors and assigns, the "Series 2012-B Purchaser" and, together with the Series 2012-A Purchaser, the "Purchasers" and each a "Purchaser").

White Mountains Insurance Group, Ltd. – 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 Line Lender and an Issuing Lender, and THE OTHER LENDERS PARTY HERETO (October 28th, 2013)

This CREDIT AGREEMENT, dated as of August 14, 2013, is among (i) WHITE MOUNTAINS INSURANCE GROUP, LTD., a company existing under the laws of Bermuda (the "Borrower"), (ii) each lender from time to time party hereto (collectively, the "Lenders") and (iii) WELLS FARGO BANK, NATIONAL ASSOCIATION ("Wells Fargo Bank"), as Administrative Agent, Swing Line Lender and an Issuing Lender.

White Mountains Insurance Group, Ltd. – FIRST SUPPLEMENTAL INDENTURE to the INDENTURE Dated as of November 9, 2012 (March 1st, 2013)

THIS FIRST SUPPLEMENTAL INDENTURE (this "Supplemental Indenture"), dated as of November 9, 2012, is among ONEBEACON U.S. HOLDINGS, INC., a Delaware corporation (the "Company"), ONEBEACON INSURANCE GROUP, LTD., a company existing under the laws of Bermuda (the "Guarantor"), and THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., a national banking association, as trustee (the "Trustee").

White Mountains Insurance Group, Ltd. – Onebeacon's 2012 Management Incentive Plan (March 1st, 2013)

The Management Incentive Plan (MIP) is an integral part of the total compensation program for managers and certain senior key individual contributors. Its primary purpose is to focus attention on 2012 profitability goals and to reward eligible participants for the achievement of those goals.

White Mountains Insurance Group, Ltd. – OneBeacon Deferred Compensation Plan (March 1st, 2013)

White Mountains Insurance Group, Ltd. – Senior Indenture (March 1st, 2013)

SENIOR INDENTURE (this "Indenture") among ONEBEACON INSURANCE GROUP, LTD. a company existing under the laws of Bermuda (the "Guarantor") having its principal office at 601 Carlson Parkway, Minnetonka, Minnesota 55305, ONEBEACON U.S. HOLDINGS, INC., a Delaware corporation (the "Company") having its principal office at 601 Carlson Parkway, Minnetonka, Minnesota 55305, and The Bank of New York Mellon Trust Company, N.A., trustee (hereinafter called the "Trustee"), is made and entered into as of this 9th day of November, 2012.

White Mountains Insurance Group, Ltd. – Regulation 114 Trust Agreement (October 30th, 2012)

This Regulation 114 Trust Agreement, dated as of July 20, 2012 (this "Trust Agreement"), is entered into by and among BUILD AMERICA MUTUAL ASSURANCE COMPANY, a corporation organized and existing under the laws of New York (the "Beneficiary"), HG RE LTD., an exempted Bermuda limited company (the "Grantor"), and THE BANK OF NEW YORK MELLON, a banking corporation organized and existing under the laws of the State of New York (the "Trustee"), (the Grantor, the Beneficiary and the Trustee are hereinafter each sometimes referred to individually as a "Party" and collectively as the "Parties").

White Mountains Insurance Group, Ltd. – Stock Purchase Agreement by and Among Onebeacon Insurance Group Llc, Onebeacon Insurance Group, Ltd., Trebuchet Us Holdings, Inc. And (October 30th, 2012)

This STOCK PURCHASE AGREEMENT (this "Agreement") is dated as of October 17, 2012, by and among OneBeacon Insurance Group LLC, a limited liability company organized under the laws of the State of Delaware ("Seller"), Trebuchet US Holdings, Inc., a corporation incorporated under the laws of the State of Delaware ("Purchaser"), and solely for purposes of Section 7.3 and Article IX, OneBeacon Insurance Group, Ltd., an exempt limited liability company organized under the laws of Bermuda ("Seller Parent"), and solely for purposes of Articles II and IX Armour Group Holdings Limited, an exempt limited liability company organized under the laws of Bermuda ("Purchaser Parent").

White Mountains Insurance Group, Ltd. – Supplemental Trust Agreement (October 30th, 2012)

This Supplemental Trust Agreement, dated as of July 20, 2012 (this "Supplemental Trust Agreement"), is entered into by and among BUILD AMERICA MUTUAL ASSURANCE COMPANY, a corporation organized and existing under the laws of New York (the "Beneficiary"), HGR PATTON (LUXEMBOURG) S.a r.l., United States of America Branch, the United States branch of a Luxembourg limited liability company (the "Grantor"), and THE BANK OF NEW YORK MELLON, a banking corporation organized and existing under the laws of the State of New York (the "Trustee"), (the Grantor, the Beneficiary and the Trustee are hereinafter each sometimes referred to individually as a "Party" and collectively as the "Parties").

White Mountains Insurance Group, Ltd. – SURPLUS NOTE PURCHASE AGREEMENT Between (October 30th, 2012)

This SURPLUS NOTE PURCHASE AGREEMENT, dated as of July 17, 2012, is made by and between Build America Mutual Assurance Company, a New York mutual insurance company (together with its successors and assigns, the "Company" or the "Issuer"), HG Holdings Ltd., an exempted Bermuda limited company (together with its successors and assigns, the "Series 2012-A Purchaser"), and HG Re Ltd., an exempted Bermuda limited company (together with its successors and assigns, the "Series 2012-B Purchaser" and, together with the Series 2012-A Purchaser, the "Purchasers" and each a "Purchaser").