wtm-20211231.htm

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Exhibit 4

DESCRIPTION OF COMMON SHARES

The summary of the terms of White Mountains’s common shares set forth below does not purport to be complete and is qualified in its entirety by reference to our memorandum of continuance and bye-laws.

Authorized Share Capital

White Mountains's memorandum of continuance and bye-laws provide that its authorized share capital is limited to 50,000,000 common shares, par value U.S. $1.00 per share. As of February 23, 2022, 3,000,849 common shares were issued and outstanding.

Voting

The holders of common shares are entitled to one vote per share except as restricted by the voting limitation described below (subject to the rights of the holders of any other class of shares that may be issued). All actions submitted to a vote of shareholders shall be voted on by the holders of common shares, voting together as a single class, except as provided by law.

With respect to the election of directors, each holder of common shares entitled to vote at the election has the right to vote, in person or by proxy, the number of shares held by him or her for as many persons as there are directors to be elected and for whose election that holder has a right to vote. The directors are divided into three classes with staggered terms, with only one class standing for election each year. Each nominee receiving the majority of the votes cast at a meeting duly called and constituted shall be elected a director of the company; provided, however, that (i) in a contested director election in which the number of nominees exceeds the number of directors to be elected, the nominees receiving the highest number of votes, up to the number of directors to be elected, shall be elected (a “Plurality Vote”); and (ii) in an uncontested election, any director who receives less than a majority of the votes cast with respect to that director’s election shall tender his or her resignation, but if such resignation is declined by the board of directors of White Mountains in accordance with the bye-laws, such director shall be elected by a Plurality Vote.

The bye-laws contain a provision limiting the voting rights of any person who beneficially holds (directly, indirectly or constructively under the Internal Revenue Code) 10% or more of the votes conferred by the issued shares of White Mountains to 9.9% of the votes conferred by the issued shares of White Mountains. This 9.9% voting limitation provision will not be applicable to any foundation or trust established by John J. Byrne, Patrick M. Byrne (his son) and/or any affiliate or associate of any of them or any group of which any of them is a part (each of them, a "Byrne Entity") with respect to any matter submitted to shareholders other than with respect to the election of directors.

In addition, the bye-laws contain a provision limiting the voting rights of any group (defined as two or more persons acting as a partnership, syndicate or other group for the purpose of acquiring, holding or disposition of the relevant securities) which beneficially holds 10% or more of the votes conferred by the issued shares of White Mountains to 9.9% of the votes conferred by the issued shares of White Mountains, except that this provision will not restrict (a) any Byrne Entity or (b) any person or group that the board of directors, by the affirmative vote of at least 75% of the entire board of directors, may exempt from this provision.

The bye-laws also contain a provision limiting the voting rights of any person to a reduced percentage who, at his or her election, notifies the board of directors to the percentage designated by such person (subject to acceptance of such cut-back by the board in its sole discretion) so that (and to the extent) such person may meet any applicable insurance or other regulatory requirement or voting threshold or limitation that may be applicable to such person or to evidence that such person's voting power is no greater than such threshold.

Dividends

Holders of common shares are entitled to participate, on a share-for-share basis, with the holders of any other common shares outstanding, with respect to any dividends declared by the board of directors of White Mountains. Dividends will generally be payable in U.S. dollars.

Liquidation

On a liquidation of White Mountains, holders of common shares are entitled to receive any assets remaining after the payment of White Mountains’s debts and the expenses of the liquidation, subject to such special rights as may be attached to any other class of shares.

Redemption

White Mountains is entitled to redeem common shares from a shareholder at fair market value if its board of directors determines that common share ownership by that shareholder may result in adverse tax, regulatory or legal consequences to White Mountains, any of its subsidiaries or any of the holders of common shares.

Variation of Rights

Under the bye-laws, if at any time White Mountains's share capital is divided into different classes of shares, the rights attached to any class (unless otherwise provided by the terms of the issue of the shares of that class) may be varied with the consent in writing of the holders of a majority of the issued shares of that class or with the sanction of a resolution passed at a separate general meeting of the holders of the shares of that class.

Change of Control

Bermuda law permits an amalgamation or a merger between two or more Bermuda companies subject, unless the bye-laws otherwise provide, to obtaining a majority vote of three-fourths of the shareholders of each of the companies, and of each class of shares entitled to vote separately as a class at such a meeting, present and voting in person or by proxy at a meeting called for that purpose. Unless the bye-laws otherwise provide, Bermuda law also requires that the quorum at the meetings be at least two persons holding or representing by proxy one-third of the issued shares of the company or the class, as the case may be. Each share of an amalgamating or merging company carries the right to vote in respect of an amalgamation or merger, whether or not it otherwise carries the right to vote.

Except as set forth in the next paragraph, the bye-laws provide that any amalgamation or merger approved by two-thirds of White Mountains's board of directors shall only require approval by a majority of the voting power held by the shareholders present at a meeting of the shareholders where a quorum is present.

White Mountains's bye-laws generally prohibit us from engaging in a "business combination" with an "interested shareholder" for a period of three years after the time of the transaction in which the person became an interested shareholder, unless:

(1) prior to that time, the board of directors approves the transaction or the business combination;

(2) upon consummation of the transaction which resulted in the shareholder becoming an interested shareholder, the interested shareholder owned at least 85% of the outstanding voting shares, excluding for purposes of determining the number of shares outstanding, shares owned by directors who are also officers and by certain employee plans; or

(3) on or after that time the board of directors and the shareholders by an affirmative vote of at least 662/3% of the outstanding voting shares, which are not owned by the interested shareholder, approve the transaction.

The definition of "business combinations" includes mergers, asset sales and other transactions resulting in a financial benefit to the interested shareholder. An "interested shareholder" is a person who, together with affiliates and associates, owns or, within three years, did own 15% or more of White Mountains's voting stock. However, the bye-laws provide that each Byrne Entity is excepted from being an "interested shareholder".

Bermuda law also provides that where an offer is made for shares in a company by another company and, within four months of the offer, the holders of at least 90% in value of the shares which are the subject of the offer (other than shares already held by or on behalf of the offeror) accept, the offeror may by notice, given within two months after such approval is obtained, require any non-tendering shareholder to transfer their shares on the terms of the offer. Dissenting shareholders may apply to a court within one month of notice objecting to the transfer and the court may make any order it thinks fit. The burden is on the dissenting shareholders to show that the court should exercise its discretion to enjoin the required transfer, which the court will be unlikely to do unless there is evidence of fraud or bad faith or collusion between the offeror and the holders of the shares who have accepted the offer as a means of unfairly forcing out minority shareholders.

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Exhibit 21

SUBSIDIARIES OF THE REGISTRANT

AS OF DECEMBER 31, 2021


FULL NAME OF SUBSIDIARY			PLACE OF INCORPORATION
ARK INSURANCE HOLDINGS LIMITED			BERMUDA
BRIDGE HOLDINGS (BERMUDA) LTD			BERMUDA
GROUP ARK INSURANCE HOLDINGS LIMITED			BERMUDA
GROUP ARK INSURANCE LIMITED			BERMUDA
HG GLOBAL LTD			BERMUDA
HG HOLDINGS LTD			BERMUDA
HG RE LTD			BERMUDA
HG SERVICES LTD			BERMUDA
PSC HOLDINGS LTD.			BERMUDA
WHITE MOUNTAINS INVESTMENTS (BERMUDA) LTD.			BERMUDA
WM HINSON (BERMUDA) LTD			BERMUDA
ATTORNEY'S & PROFESSIONAL INSURANCE SERVICES, INC.			CALIFORNIA, USA
NSM ADMINISTRATION, INC			CALIFORNIA, USA
ARK UNDERWRITING INC			CONNECTICUT, USA
AMERICAN COLLECTOR'S INSURANCE, LLC			DELAWARE, USA
COPPER FUNDING, LLC			DELAWARE, USA
J.C. TAYLOR, LLC			DELAWARE, USA
KUDU INVESTMENT HOLDINGS, LLC			DELAWARE, USA
KUDU INVESTMENT MANAGEMENT LLC			DELAWARE, USA
KUDU INVESTMENT US, LLC			DELAWARE, USA
NSM INSURANCE HOLDING CO, LLC			DELAWARE, USA
NSM INSURANCE GROUP, LLC			DELAWARE, USA
TK PARTNERS, LLC			DELAWARE, USA
WHITE MOUNTAINS ADVISORS LLC			DELAWARE, USA
WHITE MOUNTAINS CAPITAL, LLC			DELAWARE, USA
WHITE MOUNTAINS CATSKILL HOLDINGS, INC			DELAWARE, USA
WM ADAMS HOLDINGS, INC			DELAWARE, USA
WM JEFFERSON HOLDINGS, INC			DELAWARE, USA
WM LAFEYETTE HOLDINGS, INC			DELAWARE, USA
WM LINCOLN HOLDINGS, LLC			DELAWARE, USA
WM MADISON HOLDINGS, INC			DELAWARE, USA
WM PORTFOLIO HOLDINGS, LLC			DELAWARE, USA
WHITE MOUNTAINS SERVICES LLC			DELAWARE, USA
HGR PORTFOLIO SOLUTIONS ICAV			IRELAND
TNUVA FINANCIT LTD			ISRAEL
WOBI INSURANCE AGENCY, LTD			ISRAEL
WHITE MOUNTAINS HOLDINGS (LUXEMBOURG) S.A.R.L.			LUXEMBOURG
WHITE MOUNTAINS INVESTMENTS (LUXEMBOURG) S.A.R.L			LUXEMBOURG
CLEVERLAND HOLDINGS, LLC			OHIO, USA
EMBRACE PET INSURANCE AGENCY, LLC			OHIO, USA
EMBRACE PET MANAGEMENT, LLC			OHIO, USA
PLANS LIABILITY INSURANCE COMPANY			OHIO, USA
NSM INSURANCE SERVICES LLC			TEXAS, USA
ACCIDENT & HEALTH UNDERWRITING LIMITED			UNITED KINGDOM
ACCIDENT & HEALTH CLAIMS LLP			UNITED KINGDOM
ARK CORPORATE MEMBER LIMITED			UNITED KINGDOM
ARK CORPORATE MEMBER NO. 2 LIMITED			UNITED KINGDOM
ARK CORPORATE MEMBER NO. 3 LIMITED			UNITED KINGDOM
ARK CORPORATE MEMBER NO. 4 LIMITED			UNITED KINGDOM
ARK SYNDICATE MANAGEMENT LIMITED			UNITED KINGDOM
AUTOSAINT LIMITED			UNITED KINGDOM
BATSON BIDCO LIMITED			UNITED KINGDOM

Exhibit 21


BATSON MIDCO LIMITED			UNITED KINGDOM
DINGHY LIMITED			UNITED KINGDOM
DINGHY TECH LIMITED			UNITED KINGDOM
DINGHY UK LIMITED			UNITED KINGDOM
DINGHY USA INC.			UNITED KINGDOM
FIRST INSURANCE SERVICES LIMITED			UNITED KINGDOM
FIRST UNDERWRITING LTD			UNITED KINGDOM
FIRST SPECIALTY LTD			UNITED KINGDOM
FRESH INSURANCE SERVICES GROUP LIMITED			UNITED KINGDOM
KINGFISHER INSURANCE SERVICES LIMITED			UNITED KINGDOM
KINGFISHER UK HOLDINGS LIMITED			UNITED KINGDOM
KINGSBRIDGE GROUP LIMITED			UNITED KINGDOM
KINGSBRIDGE RISK SOLUTIONS LIMITED			UNITED KINGDOM
KINGSBRIDGE PROFESSIONAL SOLUTIONS LTD			UNITED KINGDOM
KRS LION BIDCO LIMITED			UNITED KINGDOM
KFO HOLDINGS LTD			UNITED KINGDOM
KWCP HOLDINGS UK LTD			UNITED KINGDOM
LADYBIRD INSURANCE BROKER LIMITED			UNITED KINGDOM
LARSEN HOWIE LIMITED			UNITED KINGDOM
LARSEN HOWIE GROUP LIMITED			UNITED KINGDOM
MAYBURY JAMES LIMITED			UNITED KINGDOM
NSM MGA HOLDINGS			UNITED KINGDOM
NSM UK HOLDINGS LTD.			UNITED KINGDOM
PETER D. JAMES LIMITED			UNITED KINGDOM
SOAR NEWCO LIMITED			UNITED KINGDOM
STEWART MILLER MCCULLOCH & CO. LIMITED			UNITED KINGDOM
STEWART MILLER MCCULLOCH (HOLDINGS) LIMITED			UNITED KINGDOM
SYNDICATE ARK 4020			UNITED KINGDOM
SYNDICATE NOA 3902			UNITED KINGDOM
WM CAPITAL HOLDINGS LTD			UNITED KINGDOM
WM INTERNATIONAL HOLDINGS LTD			UNITED KINGDOM
WM REGENT, LTD			UNITED KINGDOM
RICHMOND RISK MANAGEMENT, INC			VIRGINIA, USA

Certain other subsidiaries of the Company have been omitted since, in the aggregate, they would not constitute a significant subsidiary.

Document

Exhibit 23.1

CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

We hereby consent to the incorporation by reference in the Registration Statements on Form S-8 (Nos. 333-220469 and 333-83206) of White Mountains Insurance Group, Ltd. of our report dated February 28, 2022 relating to the financial statements, financial statement schedules and the effectiveness of internal control over financial reporting, which appears in this Form 10-K.

/s/ PricewaterhouseCoopers LLP
Boston, Massachusetts
February 28, 2022

Document

Exhibit 23.2

CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

We hereby consent to the incorporation by reference in the Registration Statements on Form S-8 (Nos. 333-220469 and 333-83206) of White Mountains Insurance Group, Ltd. of our report dated February 28, 2022 relating to the financial statements, financial statement schedule and the effectiveness of internal control over financial reporting of MediaAlpha, Inc., which appears in MediaAlpha, Inc.’s Annual Report on Form 10-K for the year ended December 31, 2021.

/s/ PricewaterhouseCoopers LLP
Boston, Massachusetts
February 28, 2022

Document

Exhibit 23.3

CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

We hereby consent to the incorporation by reference in the Registration Statements on Form S-8 (Nos. 333-220469 and 333-83206) of White Mountains Insurance Group, Ltd. of our report dated March 30, 2020 relating to the financial statements of QL Holdings, LLC, which appears in White Mountains Insurance Group, Ltd.’s Annual Report on Form 10-K/A for the year ended December 31, 2019.

/s/ PricewaterhouseCoopers LLP
Boston, Massachusetts
February 28, 2022

Document

Exhibit 24

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Peter M. Carlson does hereby make, constitute and appoint G. Manning Rountree and himself, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 22nd day of February, 2022.

/s/ Peter M. Carlson

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Mary C. Choksi does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 22nd day of February, 2022.

/s/ Mary C. Choksi

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Morgan W. Davis does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 21st day of February, 2022.

/s/ Morgan W. Davis

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Margaret Dillon does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 21st day of February, 2022.

/s/ Margaret Dillon

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Philip A. Gelston does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 21st day of February, 2022.

/s/ Philip A. Gelston

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that Suzanne Shank does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 21st day of February, 2022.

/s/ Suzanne Shank

WHITE MOUNTAINS INSURANCE GROUP, LTD.

POWER OF ATTORNEY

KNOW ALL MEN by these presents, that David A. Tanner does hereby make, constitute and appoint G. Manning Rountree and Peter M. Carlson, and each of them, as true and lawful attorney-in-fact and agent of the undersigned, with full power of substitution, resubstitution and revocation, for and in the name, place and stead of the undersigned, to execute and deliver the Annual Report on Form 10-K, and any and all amendments thereto; such Form 10-K and each such amendment to be in such form and to contain such terms and provisions as said attorney or substitute shall deem necessary or desirable; giving and granting unto said attorney, or to such person or persons as in any case may be appointed pursuant to the power of substitution herein given, full power and authority to do and perform any and every act and thing whatsoever requisite, necessary or, in the opinion of said attorney or substitute, able to be done in and about the premises as fully and to all intents and purposes as the undersigned might or could do if personally present, hereby ratifying and confirming all that said attorney or such substitute shall lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned has duly executed these presents this 21st day of February, 2022.

/s/ David A. Tanner

Document

Exhibit 31.1

PRINCIPAL EXECUTIVE OFFICER CERTIFICATION PURSUANT TO RULE 13a-14(a)

OF THE SECURITIES EXCHANGE ACT OF 1934

I, G. Manning Rountree, Chief Executive Officer of White Mountains Insurance Group, Ltd., certify that:

I have reviewed this Annual Report on Form 10-K for the fiscal year ended December 31, 2021 of White Mountains Insurance Group, Ltd.;

Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

(a)Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

(b)Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

(c)Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d)Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the registrant's most recent fiscal quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors:

(a)All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report financial information; and

(b)Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

February 28, 2022

By:

/s/ G. Manning Rountree

Chief Executive Officer

(Principal Executive Officer)

C-1

Document

Exhibit 31.2

PRINCIPAL FINANCIAL OFFICER CERTIFICATION PURSUANT TO RULE 13a-14(a)

OF THE SECURITIES EXCHANGE ACT OF 1934

I, Reid T. Campbell, Executive Vice President & Chief Financial Officer of White Mountains Insurance Group, Ltd. certify that:

I have reviewed this Annual Report on Form 10-K for the fiscal year ended December 31, 2021 of White Mountains Insurance Group, Ltd.;

(b)Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

February 28, 2022

By:

/s/ Reid T. Campbell

Executive Vice President and Chief Financial Officer

(Principal Financial Officer)

C -2

Document

Exhibit 32.1

PRINCIPAL EXECUTIVE OFFICER

CERTIFICATION PURSUANT TO

18 U.S.C. SECTION 1350,

AS ADOPTED PURSUANT TO

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

In connection with the Annual Report on Form 10-K of White Mountains Insurance Group, Ltd. (the “Company”), for the period ending December 31, 2021 as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, G. Manning Rountree, Chief Executive Officer of the Company, certify, pursuant to 18 U.S.C. §1350, as adopted pursuant to §906 of the Sarbanes-Oxley Act of 2002, that to my knowledge:

(a) The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and,

(b) The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company as of and for the periods presented in the Report.


/s/ G. Manning Rountree
Chief Executive Officer (Principal Executive Officer)

February 28, 2022

C - 3

Document

Exhibit 32.2

PRINCIPAL FINANCIAL OFFICER

CERTIFICATION PURSUANT TO

18 U.S.C. SECTION 1350,

AS ADOPTED PURSUANT TO

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

In connection with the Annual Report on Form 10-K of White Mountains Insurance Group, Ltd. (the “Company”), for the period ending December 31, 2021 as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Reid T. Campbell, Executive Vice President and Chief Financial Officer of the Company, certify, pursuant to 18 U.S.C. §1350, as adopted pursuant to §906 of the Sarbanes-Oxley Act of 2002, that to my knowledge:

(a) The Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and,


/s/ Reid T. Campbell
Executive Vice President and Chief Financial Officer (Principal Financial Officer)

February 28, 2022

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