WTM / White Mountains Insurance Group, Ltd. - Pemfailan SEC, Laporan Tahunan, Penyata Proksi

White Mountains Insurance Group, Ltd.
US ˙ NYSE ˙ BMG9618E1075

Statistik Asas
LEI 549300N3FL068JERBG02
CIK 776867
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to White Mountains Insurance Group, Ltd.
SEC Filings (Chronological Order)
Halaman ini menyediakan senarai kronologi lengkap bagi Pemfailan SEC, tidak termasuk pemfailan pemilikan yang kami sediakan di tempat lain.
September 3, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 September 2, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 September 2, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

September 2, 2025 EX-99.1

CONTACT: Rob Seelig (603) 640-2212LIAM CAFFREY TO BECOME CEO OF WHITE MOUNTAINS IN 2026

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212LIAM CAFFREY TO BECOME CEO OF WHITE MOUNTAINS IN 2026 HAMILTON, Bermuda September 2, 2025 - White Mountains Insurance Group, Ltd. (NYSE: WTM) ("White Mountains") announced today that its Board of Directors has unanimously elected Liam Caffrey as Chief Executive Officer, effective January 1, 2026. In addition, Mr. Caffrey will join the White Mountains

September 2, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 September 2, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 September 2, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

August 7, 2025 EX-10.4

Unit Purchase Agreement, dated as of July 4, 2025, by and among, AQ Phoenix Parent, L.P., WM Monroe Holdings, Inc., White Mountains Insurance Group, Ltd., and the other parties thereto

wtmexhibit104 EXECUTION VERSION [[6907028]] UNIT PURCHASE AGREEMENT by and among AQ PHOENIX PARENT, L.

August 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

August 7, 2025 EX-10.5

, 2025 among Kudu Investment Holdings, LLC, Kudu Investment US, LLC, Kudu Investment Management

wtmexhibit105 Execution Version USActive 60444630.2 Fourth Amendment to Loan and Servicing Agreement This Fourth Amendment to Loan and Servicing Agreement, dated as of July 21, 2025 (the “Fourth Amendment”), is entered into by and among KUDU INVESTMENT HOLDINGS, LLC, as the Administrative Borrower and as a Co-Borrower (“Kudu”), KUDU INVESTMENT US, LLC, as a Co-Borrower (“Kudu US” and, collectively

August 7, 2025 EX-99.1

WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON, Bermuda (August 7, 2025) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,804 as of June 30, 2025, an increase of 3% for both the second quarter of 2025 and the first six months of 2025, including dividends. Manning Rountree, CEO, commented, “BVPS was up 3

August 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

July 18, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 July 18, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

July 18, 2025 EX-99.1

BroadStreet Partners Completes Strategic Investment

Exhibit 99.1 BroadStreet Partners Completes Strategic Investment COLUMBUS, Ohio-(BUSINESS WIRE)-BroadStreet Partners (“BroadStreet” or the “Company”) today announced the successful closing of a strategic investment by an investor group led by Ethos Capital (“Ethos”), British Columbia Investment Management Corporation (“BCI”), and White Mountains Insurance Group, Ltd. (“White Mountains”), marking a

July 16, 2025 EX-10.1

10.1 Credit Agreement, dated as of July 16, 2025, among White Mountains Insurance Group, Ltd., the lenders party thereto and Bank of America, N.A., as the administrative agent

wtmex1012025whitemountai Execution Version [[6906274]] CREDIT AGREEMENT dated as of July 16, 2025, among WHITE MOUNTAINS INSURANCE GROUP, LTD.

July 16, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 July 16, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

July 7, 2025 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR o TRANSITION REPORT PURSUANT TO SECTION 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-8993 A. Full title of the plan and the address of

July 7, 2025 EX-99.1

Safe Harbor Statement under the Private Securities Litigation Reform Act of 1995

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 HAMILTON, Bermuda, July 7, 2025 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) announced today that it has entered into an agreement to acquire a majority stake in Distinguished Programs (“Distinguished” or the “Company”), an MGA and program administrator for specialty property & casualty insurance. Following the acqui

July 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 July 4, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 July 4, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 6, 2025 EX-99.1

White Mountains Insurance Group, Ltd. 2025 Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securitie

White Mountains Insurance Group, Ltd. 2025 Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or reference

June 6, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 6, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 6, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 22, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 22, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 22, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 7, 2025 EX-99.1

WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS HAMILTON, Bermuda (May 7, 2025) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,752 as of March 31, 2025, a slight increase for the first quarter of 2025, including dividends. Manning Rountree, CEO, commented, “Book value per share ended the quarter at $1,752, up sl

May 7, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 7, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993 (

May 7, 2025 EX-10.1

Third Amendment to Loan and Servicing Agreement dated as of March 18, 2025 among Kudu Investment Holdings, LLC, Kudu Investment US, LLC, Kudu Investment Management, LLC, KFO Holdings, Ltd., KWCP Holdings UK, Ltd., Massachusetts Mutual Life Insurance Company and Alter Domus (US) LLC and Barings Finance LLC. (*)

Execution Version SK 28388 0066 11621240 v4 Third Amendment to Loan and Servicing Agreement This Third Amendment to Loan and Servicing Agreement, dated as of March 18, 2025 (the “Third Amendment”), is entered into by and among KUDU INVESTMENT HOLDINGS, LLC, as a Co-Borrower (“Kudu”), KUDU INVESTMENT US, LLC, as a Co- Borrower (“Kudu US” and, collectively with Kudu, the “Co-Borrowers”), KUDU INVESTMENT MANAGEMENT LLC, as Holdings (“Holdings”), KFO HOLDINGS, LTD.

May 7, 2025 EX-10.2

White Mountains Annual Bonus Program. (*)

EXHIBIT 10.2 WHITE MOUNTAINS ANNUAL BONUS PROGRAM Set forth below is a summary of the White Mountains Annual Bonus Program: OVERVIEW The White Mountains Annual Bonus Program (the “Program”) is an integral part of the total compensation program for employees of White Mountains Insurance Group, Ltd. (“White Mountains”) and certain of its subsidiaries (collectively, the “Company”). The Program is ove

May 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, L

April 10, 2025 EX-99.1

Ethos Capital, BCI, and White Mountains to Partner with BroadStreet and Ontario Teachers' to Drive Next Chapter of Growth

Exhibit 99.1 Ethos Capital, BCI, and White Mountains to Partner with BroadStreet and Ontario Teachers' to Drive Next Chapter of Growth COLUMBUS, Ohio & BOSTON & TORONTO-(BUSINESS WIRE)-BroadStreet Partners (“BroadStreet” or the “Company”), a leading North American insurance brokerage company, announced today that an investor group led by Ethos Capital (“Ethos”), British Columbia Investment Managem

April 10, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 April 10, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 April 10, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

April 2, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

February 28, 2025 EX-21

Subsidiaries of the Registrant (*)

Exhibit 21 SUBSIDIARIES OF THE REGISTRANT AS OF DECEMBER 31, 2024 FULL NAME OF SUBSIDIARY PLACE OF INCORPORATION BAMBOO IDE8 INSURANCE SERVICES, LLC ARIZONA, USA IDE8 RE CELL 1, INC.

February 28, 2025 EX-19

White Mountains Insurance Group, Ltd. Insider Trading Policy (*)

Exhibit 19 White Mountains Insurance Group, Ltd. Insider Trading Policy All directors, officers and employees (each a “Covered Individual”) of White Mountains Insurance Group, Ltd. and its subsidiaries (collectively, the “Company”) are subject to the provisions of this Insider Trading Policy (the “Policy”). The Policy applies not only to transactions by a Covered Individual, but also to transactio

February 28, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GRO

February 28, 2025 EX-24

Powers of Attorney (*)

Exhibit 24 WHITE MOUNTAINS INSURANCE GROUP, LTD. POWER OF ATTORNEY KNOW ALL MEN by these presents, that Reid T. Campbell 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 unde

February 28, 2025 EX-4

Description of White Mountains Common Shares

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.

February 7, 2025 EX-99.1

WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS HAMILTON, Bermuda (February 7, 2025) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,746 and adjusted book value per share of $1,834 as of December 31, 2024. Book value per share and adjusted book value per share both decreased 3% in the fourth quarter of 2024 and

February 7, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 7, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

January 8, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 January 8, 2025 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-89

November 6, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 6, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

November 6, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROU

November 6, 2024 EX-99.1

WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS HAMILTON, Bermuda (November 6, 2024) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,795 and adjusted book value per share of $1,883 as of September 30, 2024. Book value per share and adjusted book value per share increased 4% and 6% in the third quarter of 2024 and

August 7, 2024 EX-99.1

WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON, Bermuda (August 7, 2024) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,722 and adjusted book value per share of $1,777 as of June 30, 2024. Book value per share and adjusted book value per share both decreased 1% in the second quarter of 2024 and increa

August 7, 2024 EX-10.1

Fourth 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 July 1, 2024. (*)

August 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

August 7, 2024 EX-10.2

Second Amendment to Loan and Servicing Agreement dated as of June 28, 2024 among Kudu Investment Holdings, LLC, Kudu Investment US, LLC, Kudu Investment Management, LLC, KFO Holdings, Ltd., KWCP Holdings UK, Ltd., Massachusetts Mutual Life Insurance Company and Alter Domus (US) LLC and Barings Finance LLC

Execution Version USActive 60444630.2 Second Amendment to Loan and Servicing Agreement This Second Amendment to Loan and Servicing Agreement, dated as of June 28, 2024 (the “Second Amendment”), is entered into by and among KUDU INVESTMENT HOLDINGS, LLC, as a Co-Borrower (“Kudu”), KUDU INVESTMENT US, LLC, as a Co- Borrower (“Kudu US” and, collectively with Kudu, the “Co-Borrowers”), KUDU INVESTMENT

August 7, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

June 7, 2024 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 7, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 7, 2024 EX-99.1

White Mountains Insurance Group, Ltd. 2024 Annual Investor Presentation 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933

White Mountains Insurance Group, Ltd. 2024 Annual Investor Presentation 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or referenced in this pre

May 31, 2024 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o TRANSITION REPORT PURSUANT TO SECTION 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-8993 A. Full title of the plan and the address of

May 23, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 23, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 9, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 9, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993 (

May 9, 2024 SC 13D/A

MAX / MediaAlpha, Inc. / WHITE MOUNTAINS INSURANCE GROUP LTD - AMENDMENT NO. 4 Activist Investment

SC 13D/A 1 sc13da.htm AMENDMENT NO. 4 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 4) MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450V104 (CUSIP Number) Robert L. Seelig, Esq. Executive Vice President and General Counsel White Mou

May 9, 2024 EX-99.1

WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS HAMILTON, Bermuda (May 9, 2024) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,742 and adjusted book value per share of $1,797 as of March 31, 2024. Book value per share and adjusted book value per share increased 5% and 6% in the first quarter of 2024, including d

May 9, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, L

May 3, 2024 SC 13D/A

MAX / MediaAlpha, Inc. / WHITE MOUNTAINS INSURANCE GROUP LTD - SC 13D/A Activist Investment

SC 13D/A 1 wtm2024maxschedule13dano3.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 3) MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450V104 (CUSIP Number) Robert L. Seelig, Esq. Executive Vice President and General Couns

April 10, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 April 10, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

April 10, 2024 EX-99.1

GILES HARRISON TO JOIN WHITE MOUNTAINS AS EVP AND CHIEF STRATEGY OFFICER; LIAM CAFFREY NAMED PRESIDENT

Exhibit 99.1 Press Release CONTACT: Rob Seelig (603) 640-2212 GILES HARRISON TO JOIN WHITE MOUNTAINS AS EVP AND CHIEF STRATEGY OFFICER; LIAM CAFFREY NAMED PRESIDENT HAMILTON, Bermuda, April 10, 2024 - White Mountains Insurance Group, Ltd. (NYSE: WTM) announced today that Giles Harrison will become its Executive Vice President and Chief Strategy Officer on June 10, 2024. Since 2015, Mr. Harrison ha

April 10, 2024 EX-10.1

Offer Letter, dated as of February 22, 2024, between the Company and Mr.

Exhibit 10.1

April 4, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

February 26, 2024 EX-4

Description of White Mountains Common Shares

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.

February 26, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GRO

February 26, 2024 EX-21

Subsidiaries of the Registrant (*)

Exhibit 21 SUBSIDIARIES OF THE REGISTRANT AS OF DECEMBER 31, 2023 FULL NAME OF SUBSIDIARY PLACE OF INCORPORATION ARK INSURANCE HOLDINGS LIMITED 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.

February 26, 2024 EX-24

Powers of Attorney (*)

Exhibit 24 WHITE MOUNTAINS INSURANCE GROUP, LTD. POWER OF ATTORNEY KNOW ALL MEN by these presents, that Reid T. Campbell 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 unde

February 26, 2024 EX-97.1

White Mountains Insurance Group, Ltd. Recovery Policy (*)

Exhibit 97.1 WHITE MOUNTAINS INSURANCE GROUP, LTD. RECOVERY POLICY Introduction The Compensation/Nominating & Governance Committee (the “CNG Committee”) of the Board of Directors of White Mountains Insurance Group, Ltd. (the “Company”) has determined that it is in the best interest of the Company to adopt this policy to provide for the recovery of certain executive compensation in the event of an

February 23, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 22, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

February 23, 2024 EX-99.1

Reid T. Campbell Elected to the White Mountains Board

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 Reid T. Campbell Elected to the White Mountains Board HAMILTON, Bermuda, February 23, 2024 /PRNewswire/ - The Board of Directors of White Mountains Insurance Group, Ltd. (NYSE: WTM) has elected Reid T. Campbell as a director of the Company. Mr. Campbell’s election to the Board follows his retirement as President of the Company after a d

February 13, 2024 SC 13G/A

WTM / White Mountains Insurance Group, Ltd. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv02282-whitemountainsinsura.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 10)* Name of issuer: White Mountains Insurance Group Ltd Title of Class of Securities: Common Stock CUSIP Number: G9618E107 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appro

February 9, 2024 SC 13G/A

WTM / White Mountains Insurance Group, Ltd. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* White Mountains Insurance Group Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G9618E107 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the ap

February 7, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 7, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

February 7, 2024 EX-99.1

WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS HAMILTON, Bermuda (February 7, 2024) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,656 and adjusted book value per share of $1,704 as of December 31, 2023. Book value per share and adjusted book value per share both increased 7% in the fourth quarter of 2023 and

January 3, 2024 SC 13D/A

MAX / MediaAlpha, Inc. / WHITE MOUNTAINS INSURANCE GROUP LTD - SC 13D/A Activist Investment

SC 13D/A 1 wtm2024max-schedule13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 2) MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450V104 (CUSIP Number) Robert L. Seelig, Esq. Executive Vice President and General Counsel

January 3, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 January 2, 2024 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-89

December 21, 2023 EX-99.1

White Mountains Renews Lead Commitment in Ark-Sponsored Reinsurance Sidecar

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 White Mountains Renews Lead Commitment in Ark-Sponsored Reinsurance Sidecar HAMILTON, Bermuda, Dec. 21, 2023 - White Mountains Insurance Group, Ltd. (NYSE: WTM) (“White Mountains”) announced today that Ark Insurance Holdings Limited (“Ark”), its specialty property and casualty reinsurance and insurance subsidiary, has renewed Outrigger

December 21, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 21, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

November 6, 2023 EX-99.1

WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS HAMILTON, Bermuda (November 6, 2023) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,542 and adjusted book value per share of $1,588 as of September 30, 2023. Book value per share and adjusted book value per share both increased 1% in the third quarter of 2023 and 6

November 6, 2023 EX-10.1

Agreement and Plan of Merger by and among PM Holdings LLC, WM Pierce Merger Sub LLC, White Mountains Insurance Group, LTD., Bamboo Ide8 Insurance Services LLC and John Chu, as the Unitholders’ Representative, dated as of October 19, 2023 (incorporated by reference herein to Exhibit 10.1 of the Company’s Report on Form 10-Q dated November 6, 2023)

EXECUTION VERSION [[6200550v1]][[6200550v1]] AGREEMENT AND PLAN OF MERGER by and among PM HOLDINGS LLC, WM PIERCE MERGER SUB LLC, WHITE MOUNTAINS INSURANCE GROUP, LTD.

November 6, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 6, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

November 6, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROU

November 2, 2023 SC 13D/A

MAX / MediaAlpha Inc - Class A / WHITE MOUNTAINS INSURANCE GROUP LTD - SC 13D/A Activist Investment

SC 13D/A 1 wtm2023max-schedule13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 1) MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450V104 (CUSIP Number) Robert L. Seelig, Esq. Executive Vice President and General Counsel

October 20, 2023 EX-99.1

White Mountains to Acquire a Majority Stake in Bamboo

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 White Mountains to Acquire a Majority Stake in Bamboo HAMILTON, Bermuda, October 20, 2023 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) (“White Mountains”) announced today that it has entered into an agreement to acquire a majority stake in Bamboo Ide8 Insurance Services, LLC (“Bamboo”), an MGA focused on the Californ

October 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 October 19, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 October 19, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

August 7, 2023 EX-10.1

Third 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 January 15, 2020

wtmq22023ex101 Execution Copy THIRD AMENDED AND RESTATED SURPLUS NOTE PURCHASE AGREEMENT Between BUILD AMERICA MUTUAL ASSURANCE COMPANY, as Issuer and HG HOLDINGS LTD.

August 7, 2023 EX-10.2

Third 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 January 15, 2020

wtmq22023ex102 NY01/ 7269182.9 THIRD AMENDED AND RESTATED SUPPLEMENTAL TRUST AGREEMENT This Third Amended and Restated Supplemental Trust Agreement, dated as of January 15, 2020, (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”), HG RE LTD., an exempted Berm

August 7, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

August 7, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

August 7, 2023 EX-10.3

dated as of June 28, 2023 among Kudu Investment Management, LLC, Kudu Investment Holdings, LLC, Kudu Investments US, LLC, KFO Holdings, Ltd., KWCP Holdings UK, Ltd., Massachusetts Mutual Life Insurance Company and Alter Domus.

wtmq22023ex103 Execution Version USActive 58806254.4 SK 28388 0001 10656491 v3 First Amendment to Loan and Servicing Agreement This First Amendment to Loan and Servicing Agreement, dated as of June 28, 2023 (the “First Amendment”), is entered into by and among KUDU INVESTMENT HOLDINGS, LLC, as a Co-Borrower (“Kudu”), KUDU INVESTMENT US, LLC, as a Co-Borrower (“Kudu US” and, collectively with Kudu,

August 7, 2023 EX-99.1

WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON, Bermuda (August 7, 2023) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,532 and adjusted book value per share of $1,576 as of June 30, 2023. Book value per share and adjusted book value per share both increased 1% in the second quarter of 2023 and increa

June 30, 2023 EX-99.1

Joint Filing Agreement, dated as of June 30, 2023, among the Reporting Persons.

EX-99.1 2 ex99-1.htm Exhibit 99.1 EXECUTION VERSION JOINT FILING AGREEMENT This Joint Filing Agreement, dated as of June 30, 2023 (this “Agreement”), is among White Mountains Insurance Group, Ltd. (“White Mountains”), WM Birkdale, Ltd. (“WM Birkdale”), White Mountains Investments (Luxembourg) S.à r.l (“WMI Lux”) and WM Hinson (Bermuda) Ltd. (“WM Hinson” and, collectively with White Mountains, WM B

June 30, 2023 SC 13D

MAX / MediaAlpha Inc - Class A / WHITE MOUNTAINS INSURANCE GROUP LTD Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450V104 (CUSIP Number) Robert L. Seelig, Esq. Executive Vice President and General Counsel White Mountains Insurance Group, Ltd. 23 South Main Street, Suite 3

June 30, 2023 EX-99.(A)(5)(III)

Press Release issued by White Mountains Insurance Group, Ltd., dated June 30, 2023.*

Exhibit (a)(5)(iii) White Mountains Insurance Group, Ltd. Announces the Final Results of White Mountains Insurance Group, Ltd. and WM Hinson (Bermuda) Ltd.’s Tender Offer for up to 5,916,816 Shares of Class A Common Stock of MediaAlpha, Inc. HAMILTON, Bermuda, June 30, 2023 -  White Mountains Insurance Group, Ltd. (NYSE: WTM) (“White Mountains”) today announced the final results of the cash tender

June 30, 2023 EX-FILING FEES

Filing Fee Table*

Exhibit 107 Calculation of Filing Fee Table Table 1: Transaction Valuation Transaction Valuation Fee rate Amount of Filing Fee Fees to Be Paid $ 9,168,160.

June 30, 2023 SC TO-T/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 2 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) W

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 2 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) White Mountains Insurance Group, Ltd. WM Hinson (Bermuda) Ltd. (Names of Filing Persons (Offerors)) Class A Common Stock, par value $0.01 per share

June 27, 2023 SC TO-T/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) W

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) White Mountains Insurance Group, Ltd. WM Hinson (Bermuda) Ltd. (Names of Filing Persons (Offerors)) Class A Common Stock, par value $0.01 per share

June 27, 2023 EX-99.(A)(5)(II)

Press Release issued by White Mountains Insurance Group, Ltd., dated June 27, 2023.*

Exhibit (a)(5)(ii) White Mountains Insurance Group, Ltd. Announces the Preliminary Results of White Mountains Insurance Group, Ltd. and WM Hinson (Bermuda) Ltd.’s Tender Offer for up to 5,000,000 Shares of Class A Common Stock of MediaAlpha, Inc. HAMILTON, Bermuda, June 27, 2023 - White Mountains Insurance Group, Ltd. (NYSE: WTM) (“White Mountains”) today announced the preliminary results of the c

June 15, 2023 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o TRANSITION REPORT PURSUANT TO SECTION 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-8993 A. Full title of the plan and the address of

June 6, 2023 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 6, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 6, 2023 EX-99.1

White Mountains Insurance Group, Ltd. 2023 Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securitie

White Mountains Insurance Group, Ltd. 2023 Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or reference

May 26, 2023 EX-99.(A)(1)(VI)

Text of Summary Advertisement, as published in the New York Times on May 26, 2023.*

Exhibit (a)(1)(vi) This announcement is neither an offer to purchase nor a solicitation of an offer to sell shares of the common stock of MediaAlpha, Inc.

May 26, 2023 EX-FILING FEES

Filing Fee Table*

EX-FILING FEES 9 tm2316178d2ex-filingfees.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Table Table 1: Transaction Valuation Transaction Valuation Fee rate Amount of Filing Fee Fees to Be Paid $ 50,000,000.00 * 0.00011020 $ 5,510.00 ** Fees Previously Paid $ — $ — Total Transaction Valuation $ 50,000,000.00 Total Fees Due for Filing $ 5,510.00 Total Fees Previously Paid $ — Total Fee Of

May 26, 2023 EX-99.(A)5

Press Release issued by White Mountains Insurance Group, Ltd., dated May 26, 2023.*

Exhibit (a)(5) White Mountains Insurance Group, Ltd. Announces that White Mountains Insurance Group, Ltd. and WM Hinson (Bermuda) Ltd. Commence Tender Offer for up to 5,000,000 Shares of Class A Common Stock of MediaAlpha, Inc. HAMILTON, Bermuda, May 26, 2023 -  White Mountains Insurance Group, Ltd. (NYSE: WTM) (“White Mountains”) today announced that it and its wholly owned subsidiary, WM Hinson

May 26, 2023 EX-99.(A)(1)(II)

Form of Letter of Transmittal.*

 Exhibit (a)(1)(ii) Letter of Transmittal For Tender of Shares of Class A Common Stock of MediaAlpha, Inc.

May 26, 2023 EX-99.(A)(1)(IV)

Form of Letter to Brokers, Dealers, Banks, Trust Companies and Other Nominees.*

 Exhibit (a)(1)(iv) Offer to Purchase for Cash Up to 5,000,000 Shares of Class A Common Stock of MediaAlpha, Inc.

May 26, 2023 EX-99.(A)(1)(V)

Form of Letter to Clients for Use by Brokers, Dealers, Banks, Trust Companies and Other Nominees.*

 Exhibit (a)(1)(v) Offer to Purchase for Cash Up to 5,000,000 Shares of Class A Common Stock of MediaAlpha, Inc.

May 26, 2023 SC TO-T

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) White Mountains I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 MediaAlpha, Inc. (Name of Subject Company (Issuer)) White Mountains Insurance Group, Ltd. WM Hinson (Bermuda) Ltd. (Names of Filing Persons (Offerors)) Class A Common Stock, par value $0.01 per share (Title of Class of

May 26, 2023 EX-99.(A)(1)(III)

Form of Notice of Guaranteed Delivery.*

 Exhibit (a)(1)(iii) Notice of Guaranteed Delivery For Tender of Shares of Class A Common Stock of MediaAlpha, Inc.

May 26, 2023 EX-99.(A)(1)(I)

Offer to Purchase, dated May 26, 2023.*

TABLE OF CONTENTS   Exhibit (a)(1)(i) Offer to Purchase for Cash Up to 5,000,000 Shares of Class A Common Stock of MediaAlpha, Inc.

May 25, 2023 EX-99.1

Morgan Davis Retires from White Mountains Board of Directors; Weston M. Hicks Elected Chairman

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 Morgan Davis Retires from White Mountains Board of Directors; Weston M. Hicks Elected Chairman HAMILTON, Bermuda, May 25, 2023 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) today announced that Weston M. Hicks has been elected Chairman of the Board. Mr. Hicks replaces Morgan Davis, who has retired from the Board effec

May 25, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 25, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 25, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 25, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 25, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 25, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 10, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

DEFA14A 1 defa14a2023.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Pre

May 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, L

May 9, 2023 EX-99.1

WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS HAMILTON, Bermuda (May 9, 2023) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,522 and adjusted book value per share of $1,567 as of March 31, 2023. Book value per share and adjusted book value per share both increased 5% in the first quarter of 2023. Manning Rount

May 9, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 9, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 9, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993 (

April 6, 2023 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

April 5, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

March 10, 2023 SC 13G/A

WTM / White Mountains Insurance Group, Ltd. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 9)* Name of issuer: White Mountains Insurance Group Ltd. Title of Class of Securities: Common Stock CUSIP Number: G9618E107 Date of Event Which Requires Filing of this Statement: February 28, 2023 Check the appropriate box to designate the rule pursuant to which this Sch

February 27, 2023 EX-4

Description of White Mountains Common Shares

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.

February 27, 2023 EX-24

Powers of Attorney (*)

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,

February 27, 2023 EX-21

Subsidiaries of the Registrant (*)

Exhibit 21 SUBSIDIARIES OF THE REGISTRANT AS OF DECEMBER 31, 2022 FULL NAME OF SUBSIDIARY PLACE OF INCORPORATION ARK INSURANCE HOLDINGS LIMITED 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.

February 27, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GRO

February 23, 2023 EX-99.1

Weston M. Hicks Elected to the White Mountains Board

Exhibit 99.1 PP PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 Weston M. Hicks Elected to the White Mountains Board HAMILTON, Bermuda, February 23, 2023 /PRNewswire/ - The Board of Directors of White Mountains Insurance Group, Ltd. (NYSE: WTM) has elected Weston M. Hicks as a director of the Company. Mr. Hicks was formerly the President and CEO of Alleghany Corporation. He previously has served

February 23, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 22, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 22, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

February 10, 2023 SC 13G

MAX / MediaAlpha Inc / WHITE MOUNTAINS INSURANCE GROUP LTD - SC 13G Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G* (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (AMENDMENT NO. 1)* MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, $0.01 par value per share (Title of Class of Securities) 58450V104 (CUSIP Number) December 31, 202

February 10, 2023 SC 13G

WTM / White Mountains Insurance Group Ltd / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

SC 13G 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* White Mountains Insurance Group Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G9618E107 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the approp

February 9, 2023 SC 13G/A

WTM / White Mountains Insurance Group Ltd / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv02251-whitemountainsinsura.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 8)* Name of issuer: White Mountains Insurance Group Ltd. Title of Class of Securities: Common Stock CUSIP Number: G9618E107 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appro

February 7, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 7, 2023 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

February 7, 2023 EX-99.1

WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS HAMILTON, Bermuda (February 7, 2023) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,457 and adjusted book value per share of $1,495 as of December 31, 2022. Book value per share and adjusted book value per share increased 1% and 2% in the fourth quarter of 2022. B

February 6, 2023 SC 13G/A

WTM / White Mountains Insurance Group Ltd / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4 )* White Mountains Insurance Group, Ltd. (Name of Issuer) Common Stock (Title of Class of Securities) G9618E107 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuan

December 21, 2022 EX-99.1

White Mountains Leads Investor Group in Ark-Sponsored Reinsurance Sidecar

Exhibit 99.1 - PRESS RELEASE - White Mountains Leads Investor Group in Ark-Sponsored Reinsurance Sidecar HAMILTON, Bermuda, December 21, 2022 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) (?White Mountains?) announced today that Ark Insurance Holdings Limited (?Ark?), its specialty property and casualty reinsurance and insurance subsidiary, has sponsored the formation of a reins

December 21, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 21, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

November 7, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROU

November 7, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 7, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

November 7, 2022 EX-99.1

WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS HAMILTON, Bermuda (November 7, 2022) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,439 and adjusted book value per share of $1,471 as of September 30, 2022. Book value per share and adjusted book value per share both increased 28% in the third quarter of 2022. Boo

September 26, 2022 EX-99.(A)(5)(K)

Press Release, dated September 26, 2022

? Exhibit (a)(5)(K)? PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212? WHITE MOUNTAINS ANNOUNCES FINAL RESULTS OF ITS TENDER OFFER HAMILTON, Bermuda, September 26, 2022???White Mountains Insurance Group, Ltd.

September 26, 2022 SC TO-I/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 3 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subjec

? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? AMENDMENT NO. 3 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 ? WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subject Company (Issuer) and Filing Person (Issuer and Offeror)) ? Common Shares, par value $1.00 per share (Title of Class of Securities) ? G9

September 21, 2022 SC TO-I/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 2 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subjec

? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? AMENDMENT NO. 2 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 ? WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subject Company (Issuer) and Filing Person (Issuer and Offeror)) ? Common Shares, par value $1.00 per share (Title of Class of Securities) ? G9

September 21, 2022 EX-99.(A)(5)(J)

Press Release, dated September 21, 2022

? Exhibit (a)(5)(J)? PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212? WHITE MOUNTAINS ANNOUNCES PRELIMINARY RESULTS OF ITS TENDER OFFER HAMILTON, Bermuda, September 21, 2022???White Mountains Insurance Group, Ltd.

August 30, 2022 EX-99.(A)(1)(J)

Amended and Restated Letter of Transmittal

? ?Exhibit (a)(1)(J)? AMENDED AND RESTATED LETTER OF TRANSMITTAL To Tender Common Shares (CUSIP Number G9618E107) of WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 30, 2022 SC TO-I/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Sub

? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? AMENDMENT NO. 1 TO SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 ? WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subject Company (Issuer) and Filing Person (Issuer and Offeror)) ? Common Shares, par value $1.00 per share (Title of Class of Securities) ? G9

August 22, 2022 EX-99.A5A

Press Release, dated August 22, 2022

Exhibit (a)(5)(A) PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS TO COMMENCE SELF-TENDER OFFER TO PURCHASE UP TO $500 MILLION IN VALUE OF ITS COMMON SHARES HAMILTON, Bermuda, August 22, 2022 - White Mountains Insurance Group, Ltd.

August 22, 2022 EX-99.A1A

Offer to Purchase dated August 22, 2022

TABLE OF CONTENTS ?Exhibit (a)(1)(A)? OFFER TO PURCHASE FOR CASH BY WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 22, 2022 EX-99.A1H

Letter to Participants in the White Mountains Retirement Plan, dated August 22, 2022

? ?Exhibit (a)(1)(H)? LETTER TO PARTICIPANTS IN THE WHITE MOUNTAINS RETIREMENT PLAN August 22, 2022 Dear Plan Participant: White Mountains Insurance Group, Ltd.

August 22, 2022 EX-99.A1F

Form of Summary Advertisement as published on August 22, 2022

Exhibit (a)(1)(F) This announcement is neither an offer to purchase nor a solicitation of an offer to sell shares of White Mountains Insurance Group, Ltd.

August 22, 2022 EX-99.A1D

Letter to Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees

? ?Exhibit (a)(1)(D)? OFFER TO PURCHASE FOR CASH by WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 22, 2022 EX-FILING FEES

Filing Fees

Exhibit 107 Table 1: Transaction Valuation Transaction Valuation Fee rate Amount of Filing Fee Fees to Be Paid $500,000,000 0.0000927 $46,350 Fees Previously Paid ? ? Total Transaction Valuation $500,000,000 Total Fees Due for Filing $46,350 Total Fees Previously Paid ? Total Fee Offsets ? Net Fee Due $46,350

August 22, 2022 SC TO-I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subject Company (Issue

SC TO-I 1 tm2223096-1sctoi.htm SC TO-I UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 1934 WHITE MOUNTAINS INSURANCE GROUP, LTD. (Name of Subject Company (Issuer) and Filing Person (Issuer and Offeror)) Common Shares, par value $1.00 per share (Title of Class of Securiti

August 22, 2022 EX-99.A1G

Letter from the Company’s Chief Executive Officer to Shareholders dated August 22, 2022

? ?Exhibit (a)(1)(G)? August 22, 2022? Dear Fellow Shareholder: White Mountains Insurance Group, Ltd.

August 22, 2022 EX-99.A1L

Email to Participants in the White Mountains Retirement Plan, dated August 22, 2022

Exhibit (a)(1)(I) On August 22, 2022 White Mountains Insurance Group, Ltd. announced that it has commenced a ?modified Dutch auction? self-tender offer to purchase up to $500 million in value of its common shares, at a purchase price of not greater than $1,400 nor less than $1,250 per share. As a holder of White Mountains common shares within the White Mountains Retirement Plan, you are eligible t

August 22, 2022 EX-99.A1B

Letter of Transmittal dated August 22, 2022

? ?Exhibit (a)(1)(b)? LETTER OF TRANSMITTAL To Tender Common Shares (CUSIP Number G9618E107) of WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 22, 2022 EX-99.A1C

Notice of Guaranteed Delivery

? ?Exhibit (a)(1)(C)? NOTICE OF GUARANTEED DELIVERY? (Not to be used for Signature Guarantee) WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 22, 2022 EX-99.A1E

Letter to Clients for use by Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees

? ?Exhibit (a)(1)(E)? OFFER TO PURCHASE FOR CASH by WHITE MOUNTAINS INSURANCE GROUP, LTD.

August 8, 2022 EX-99.1

WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS

EX-99.1 2 wtmq22022earningsrelease.htm EX-99.1 Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON, Bermuda (August 8, 2022) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,129 and adjusted book value per share of $1,152 as of June 30, 2022. Book value per share and adjusted book value per share decreased 5

August 8, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 8, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

August 8, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

August 5, 2022 EX-99.1

White Mountains Completes Sale of NSM

Exhibit 99.1 - PRESS RELEASE - White Mountains Completes Sale of NSM HAMILTON, Bermuda, August 1, 2022 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) (?White Mountains?) announced today that it has completed the sale of NSM Insurance Group to investment funds affiliated with global investment firm Carlyle (NASDAQ: CG). White Mountains is in a quiet period until second quarter ear

August 5, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 1, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

August 5, 2022 EX-99.2

WHITE MOUNTAINS INSURANCE GROUP, LTD. UNAUDITED PRO FORMA CONDENSED CONSOLIDATED INFORMATION

Exhibit 99.2 WHITE MOUNTAINS INSURANCE GROUP, LTD. UNAUDITED PRO FORMA CONDENSED CONSOLIDATED INFORMATION Transaction Overview On August 1, 2022, White Mountains Holdings (Luxembourg) S.? r.l. (?WTM Holdings Seller?), an indirect wholly owned subsidiary of White Mountains Insurance Group, Ltd. (?White Mountains?), completed the previously announced sale of White Mountains Catskill Holdings, Inc. (

June 14, 2022 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR o TRANSITION REPORT PURSUANT TO SECTION 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-8993 A. Full title of the plan and the address of

June 10, 2022 EX-99.1

White Mountains Insurance Group, Ltd. Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act

White Mountains Insurance Group, Ltd. Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or referenced in

June 10, 2022 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 10, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 26, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 26, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 26, 2022 EX-99.1

MassMutual Becomes Equity Investor in Kudu Investment Management

EX-99.1 2 wtmexhibit991kudu.htm EX-99.1 Exhibit 99.1 MassMutual Becomes Equity Investor in Kudu Investment Management NEW YORK, May 26, 2022 – Kudu Investment Management, LLC (Kudu), an independent provider of permanent capital solutions to asset and wealth managers worldwide, today announced that Massachusetts Mutual Life Insurance Company (MassMutual), a leading U.S. mutual life insurance compan

May 26, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 26, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 16, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

May 10, 2022 EX-2.1

Securities Purchase Agreement dated May 9, 2022 by and among Riser Merger Sub, Inc., White Mountains Catskill Holdings (Luxembourg) S.à r. l., NSM Insurance HoldCo, LLC and the other parties thereto

EXECUTION VERSION [[5828813]] SECURITIES PURCHASE AGREEMENT by and among RISER MERGER SUB, INC.

May 10, 2022 EX-99.1

White Mountains to Sell NSM to Carlyle

Exhibit 99.1 - PRESS RELEASE - White Mountains to Sell NSM to Carlyle HAMILTON, Bermuda and New York, NY, May 9, 2022 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) (?White Mountains?) announced today that it has signed a definitive agreement to sell NSM Insurance Group (?NSM?) to investment funds affiliated with global investment firm Carlyle (NASDAQ: CG). The transaction values

May 10, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 9, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993 (

May 6, 2022 EX-99.1

WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS

Exhibit 99.1 CONTACT: Rob Seelig (603) 640-2212 WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS HAMILTON, Bermuda (May 6, 2022) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,183 and adjusted book value per share of $1,204 as of March 31, 2022. Book value per share and adjusted book value per share both increased 1% in the first quarter of 2022. Manning Rount

May 6, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 6, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993 (

May 6, 2022 EX-10.2

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 (incorporated by reference herein to Exhibit 10.2 of the Company’s Report on Form 10-Q dated May 6, 2022) (**)

EXECUTION VERSION [[5791959]] LOAN AND SECURITY AGREEMENT dated as of March 31, 2022, among HG GLOBAL LTD.

May 6, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, L

May 6, 2022 EX-10.1

White Mountains Bonus Plan (incorporated by reference herein and filed as Exhibit 10.1 of the Company’s Quarterly Report on Form 10-Q for the period ended March 31, 2022)

EXHIBIT 10.1 WHITE MOUNTAINS ANNUAL BONUS PROGRAM Set forth below is a summary of the White Mountains Annual Bonus Program: OVERVIEW The White Mountains Annual Bonus Program (the ?Program?) is an integral part of the total compensation program for employees of White Mountains Insurance Group, Ltd. (?White Mountains?) and certain of its subsidiaries (collectively, the ?Company?). The Program is ove

April 6, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

April 1, 2022 EX-99.1

HG Global Closes New $150 Million Credit Facility

Exhibit 99.1 PRESS RELEASE CONTACT: Rob Seelig (603) 640-2212 HG Global Closes New $150 Million Credit Facility HAMILTON, Bermuda, March 31, 2022 /PRNewswire/ - White Mountains Insurance Group, Ltd. (NYSE: WTM) announced today that HG Global Ltd. (?HG?) closed a new $150 million, 10-year term loan credit facility with Hudson Structured Capital Management Ltd, (conducting its re/insurance business

April 1, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 March 31, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

February 28, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GRO

February 28, 2022 EX-24

Powers of Attorney (*)

EX-24 7 wtm10-k2021exhibit24.htm EX-24 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 nam

February 28, 2022 EX-4

Description of White Mountains Common Shares

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.

February 28, 2022 EX-21

Subsidiaries of the Registrant (*)

EX-21 3 wtm10-k2021exhibit21.htm EX-21 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 PS

February 14, 2022 SC 13G/A

MAX / MediaAlpha Inc / WHITE MOUNTAINS INSURANCE GROUP LTD - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G* (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (AMENDMENT NO. 1)* MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, $0.01 par value per share (Title of Class of Securities) 58450V104 (CUSIP Number) December 31, 202

February 10, 2022 SC 13G/A

WTM / White Mountains Insurance Group Ltd / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 7)* Name of issuer: White Mountains Insurance Group Ltd. Title of Class of Securities: Common Stock CUSIP Number: G9618E107 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to which this Sch

February 8, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 8, 2022 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

February 8, 2022 EX-99.1

WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS

Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS HAMILTON, Bermuda (February 8, 2022) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,176 and adjusted book value per share of $1,190 as of December 31, 2021. Book value per share and adjusted book value per share both increased 1% in the fourth quarter of 2021.

February 4, 2022 SC 13G/A

WTM / White Mountains Insurance Group Ltd / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3 )* White Mountains Insurance Group, Ltd. (Name of Issuer) Common Stock (Title of Class of Securities) G9618E107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuan

December 2, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 29, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

December 2, 2021 EX-99.1

LIAM CAFFREY TO BECOME CFO OF WHITE MOUNTAINS

Exhibit 99.1 PRESS RELEASE CONTACT: Todd Pozefsky (203) 458-5807 LIAM CAFFREY TO BECOME CFO OF WHITE MOUNTAINS HAMILTON, Bermuda, December 2, 2021 - White Mountains Insurance Group, Ltd. (NYSE: WTM) announced today that Liam P. Caffrey will become its Chief Financial Officer on March 1, 2022. Mr. Caffrey currently serves as a consultant to a subsidiary of the Company. Previously, Mr. Caffrey spent

December 2, 2021 EX-10.2

Consulting Agreement, dated as of November 1, 2021, between White Mountains Capital LLC and Liam Caffrey (incorporated by reference herein and filed as Exhibit 10.2 of the Company’s Current Report on Form 8-K dated November 29, 2021)

EXECUTION COPY CONSULTING AGREEMENT This agreement, made and effective as of November 1, 2021, by and between White Mountains Capital LLC (hereinafter referred to as ?Company?), and Liam Caffrey, an independent contractor, of (hereinafter referred to as ?Consultant?).

December 2, 2021 EX-10.1

Offer Letter, dated as of November 29, 2021, between the Company and Liam Caffrey (incorporated by reference herein and filed as Exhibit 10.1 of the Company’s Current Report on Form 8-K dated November 29, 2021)

G. Manning Rountree Chief Executive Officer November 29, 2021 Liam P. Caffrey Dear Liam: I am pleased to confirm your offer of employment for the position of Executive Vice President and Chief Financial Officer at White Mountains Insurance Group. You will be located in our Hanover office, and your first day of employment will be March 1, 2022. As we have discussed, the Chief Financial Officer role

November 8, 2021 EX-99.1

WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS

Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS HAMILTON, Bermuda (November 8, 2021) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,162 and adjusted book value per share of $1,176 as of September 30, 2021. Book value per share and adjusted book value per share both decreased 9% in the third quarter of 2021. F

November 8, 2021 EX-10.3

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

Exhibit 10.3 DocuSign Envelope ID: 135491C1-3E2D-4FAD-98E8-40EE4292B8F4 Duties of the Agent Bank DocuSign Envelope ID: 135491C1-3E2D-4FAD-98E8-40EE4292B8F4 Terms and Conditions Changes in Agents egulations concerning transfers and registration of Subordinated Notes Specified Offices of the Agents Redemption, Purchase and Cancellation Redemption, Purchase and Cancellation provided however that Docu

November 8, 2021 EX-10.4

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

Exhibit 10.4 CONTENTS PAGE 1 CONTENTS CLAUSE 1 DEFINITIONS AND INTERPRETATION ........................................................................... 1 2 APPOINTMENT OF AGENTS.............................................................................................. 4 3 THE SUBORDINATED NOTES ........................................................................................... 4 4 EXC

November 8, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 8, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

November 8, 2021 EX-10.1

Loan and Servicing Agreement dated as of March 23, 2021 among Kudu Investment Management, LLC, Kudu Investment Holdings, LLC, Kudu Investments US, LLC, KFO Holdings, Ltd., KWCP Holdings UK, Ltd.,

Execution Version NAI?1515108520v22 LOAN AND SERVICING AGREEMENT among KUDU INVESTMENT MANAGEMENT, LLC, as Holdings, KUDU INVESTMENT HOLDINGS, LLC, and KUDU INVESTMENT US, LLC, as the Co?Borrowers, KFO HOLDINGS, LTD.

November 8, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROU

November 8, 2021 EX-10.2

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

Reed Smith LLP 112 avenue Kl?ber 75116 Paris Phone: +33 (0)1 76 70 40 00 Fax: +33 (0)1 76 70 41 19 r e e d s m i t h .

October 12, 2021 EX-99.1

Suzanne Shank Elected to the White Mountains Board

Exhibit 99.1 PRESS RELEASE CONTACT: Todd Pozefsky (203) 458-5807 Suzanne Shank Elected to the White Mountains Board HAMILTON, Bermuda, October 12, 2021 - The Board of Directors of White Mountains Insurance Group, Ltd. (NYSE: WTM) has elected Suzanne F. Shank as a director of the Company. Ms. Shank is the President, CEO and co-founder of Siebert Williams Shank & Co., LLC, a full-service investment

October 12, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 October 10, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

September 13, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 September 8, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

August 13, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 11, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-89

August 6, 2021 EX-10

FIFTH AMENDMENT dated as of June 2, 2021, among NSM INSURANCE GROUP, LLC, a Delaware limited liability company, NSM INSURANCE HOLDCO, LLC, a Delaware limited liability company, NSM UK HOLDINGS LTD, a company incorporated in England and Wales, the other LOAN PARTIES party hereto, ARES CAPITAL CORPORATION, a Maryland corporation, as administrative agent, the LENDERS party hereto and the L/C ISSUERS party hereto.

EXECUTION VERSION [[5629532]] FIFTH AMENDMENT dated as of June 2, 2021 (this ?Amendment?), among NSM INSURANCE GROUP, LLC, a Delaware limited liability company (the ?U.

August 6, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

August 6, 2021 EX-99.1

WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS

EX-99.1 2 wtmq22021earningsrelease.htm EX-99.1 Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON, Bermuda (August 6, 2021) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,279 and adjusted book value per share of $1,292 as of June 30, 2021. Book value per share and adjusted book value per share both inc

August 6, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 6, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

July 19, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 July 13, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 29, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 29, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 15, 2021 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR o TRANSITION REPORT PURSUANT TO SECTION 15(D) OF THE Securities EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-8993 A. Full title of the plan and the address of

June 4, 2021 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 June 4, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

June 4, 2021 EX-99.1

White Mountains Insurance Group, Ltd. Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act

White Mountains Insurance Group, Ltd. Annual Investor Presentation Exhibit 99.1 1 Forward-Looking Statements Forward-Looking Statements This presentation may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or referenced in

May 28, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 27, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 10, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 May 10, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8993

May 10, 2021 EX-99.1

WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS

Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS FIRST QUARTER RESULTS HAMILTON, Bermuda (May 10, 2021) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,231 and adjusted book value per share of $1,242 as of March 31, 2021. Book value per share and adjusted book value per share both decreased 2% in the first quarter of 2021, including

May 10, 2021 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, L

April 7, 2021 DEF 14A

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

March 30, 2021 10-K/A

Annual Report - 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNT

March 16, 2021 EX-99.3

$ in millions Year ended December 31, 2020 Earned premium, net of reinsurance $ 419.6 Net claims and expenses (411.3) Syndicate investment return 3.8 Total return from syndicate operations $ 12.1 Combined ratio 98 %

Exhibit 99.3 EXHIBIT OF SYNDICATE RESULTS The following table presents a summary of the combined results of Syndicates 4020 and 3902 as reported to Lloyd?s under U.K. GAAP for the year ended December 31, 2020. $ in millions Year ended December 31, 2020 Earned premium, net of reinsurance $ 419.6 Net claims and expenses (411.3) Syndicate investment return 3.8 Total return from syndicate operations $

March 16, 2021 8-K/A

Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 January 1, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

March 16, 2021 EX-99.2

Exhibit 99.2 Contents Independent auditors’ report 2 Consolidated income statement and Consolidated statement of comprehensive income 3 Consolidated balance sheet 4 Consolidated statement of changes in equity Consolidated statement of cash flows 5 6

EX-99.2 2 wtm8-karkexhibit992.htm EX-99.2 Exhibit 99.2 Contents Independent auditors’ report 2 Consolidated income statement and Consolidated statement of comprehensive income 3 Consolidated balance sheet 4 Consolidated statement of changes in equity Consolidated statement of cash flows 5 6 Notes to the financial statements 7 Ark Insurance Holdings Limited 1 Independent auditors’ report to the Boa

February 26, 2021 EX-21

Subsidiaries of the Registrant (*)

Exhibit 21 SUBSIDIARIES OF THE REGISTRANT AS OF DECEMBER 31, 2020 FULL NAME OF SUBSIDIARY PLACE OF INCORPORATION BRIDGE HOLDINGS (BERMUDA) LTD BERMUDA HG GLOBAL LTD BERMUDA HG HOLDINGS LTD BERMUDA HG RE LTD BERMUDA HG SERVICES LTD BERMUDA PSC HOLDINGS LTD.

February 26, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GRO

February 26, 2021 EX-24

Powers of Attorney (*)

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,

February 26, 2021 EX-10.13

Employment Agreement and Release between White Mountains Capital LLC and J. Brian Palmer dated February 25, 2021 (incorporated by reference herein and filed as Exhibit 10.13 of the Company’s 2020 Annual Report on Form 10-K)

Exhibit 10.13 EMPLOYMENT AGREEMENT AND RELEASE THIS EMPLOYMENT AGREEMENT AND RELEASE (this “Agreement”) is between WHITE MOUNTAINS CAPITAL LLC (the “Company”), and J. BRIAN PALMER (the “Executive”) and shall become effective on the eighth day following its execution by Executive (the “Effective Date”), provided Executive has not revoked this Agreement during the Revocation Period (as defined in Se

February 26, 2021 EX-10.14

Employment Agreement between White Mountains Capital LLC and Frank R. Bazos dated December 16, 2020 (incorporated by reference herein and filed as Exhibit 10.14 of the Company’s 2020 Annual Report on Form 10-K)

EX-10.14 4 wtm10-k2020exhibit1014.htm EX-10.14 Exhibit 10.14 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (this “Agreement”) between WHITE MOUNTAINS CAPITAL LLC (the “Company”), and FRANK R. BAZOS (the “Executive”) is made and entered into as of December 16, 2020. WHEREAS, effective as of March 1, 2021 (the “Effective Date”), Executive will resign as Executive Vice President and Head of Mergers

February 26, 2021 EX-4

Description of White Mountains Common Shares

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.

February 12, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G* (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (AMENDMENT NO. N/A)*

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G* (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (AMENDMENT NO. N/A)* MEDIAALPHA, INC. (Name of Issuer) Class A Common Stock, $0.01 par value per share (Title of Class of Securities) 58450V104 (CUSIP Number) December 31, 2

February 10, 2021 SC 13G/A

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 6)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 6)* Name of issuer: White Mountains Insurance Group Ltd. Title of Class of Securities: Common Stock CUSIP Number: G9618E107 Date of Event Which Requires Filing of this Statement: December 31, 2020 Check the appropriate box to designate the rule pursuant to which this Sch

February 5, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 February 5, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

February 5, 2021 EX-99.1

WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS

Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS FOURTH QUARTER RESULTS HAMILTON, Bermuda (February 5, 2021) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,259 and adjusted book value per share of $1,264 as of December 31, 2020. Book value per share and adjusted book value per share both increased 15% in the fourth quarter of 2020.

February 3, 2021 SC 13G/A

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2 )* White Mountains Insurance Group, Ltd. (Name of Issuer) Common Stock (Title of Class of Securities) G9618E107 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuan

January 4, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 January 1, 2021 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-89

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 30, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 29, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 29, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 29, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 29, 2020 S-8 POS

- S-8 POS

As filed with the Securities and Exchange Commission on December 29, 2020 SECURITIES AND EXCHANGE COMMISSION Washington, D.

December 21, 2020 8-K

Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 16, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

December 21, 2020 8-K/A

- 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 9, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1

December 15, 2020 8-K

Entry into a Material Definitive Agreement - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 14, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

December 15, 2020 EX-2.1

Subscription and Purchase Agreement amended and restated on December 14, 2020 by and among Ark Insurance Holdings Limited, Bridge Holdings (Bermuda) Ltd., White Mountains Insurance Group, Ltd. and the selling shareholders party thereto

wtmex21-amendedagreement Exhibit 2.1 EXECUTION VERSION Certain identified confidential information contained in this document, marked by brackets, has been excluded from this exhibit because it is both (i) not material and (ii) would be competitively harmful if publicly disclosed. Ark Insurance Holdings Limited Subscription and Purchase Agreement CityPoint, 1 Ropemaker Street London, EC2Y 9AW TABL

December 10, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 December 9, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

December 1, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 30, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-

November 6, 2020 8-K

- 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 November 6, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-8

November 6, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended September 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROU

November 6, 2020 EX-99.1

WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS

Exhibit 99.1 CONTACT: Todd Pozefsky (203) 458-5807 WHITE MOUNTAINS REPORTS THIRD QUARTER RESULTS HAMILTON, Bermuda (November 6, 2020) - White Mountains Insurance Group, Ltd. (NYSE: WTM) reported book value per share of $1,099 and adjusted book value per share of $1,101 as of September 30, 2020. Book value per share and adjusted book value per share both increased 8% in the third quarter of 2020. F

October 1, 2020 EX-2.2

by and among Ian Beaton, Nicholas Bonnar, Neil Smith and Bridge Holdings (Bermuda) Ltd.

wtm22exhibit Execution Version Certain identified confidential information contained in this document, marked by brackets, has been excluded from this exhibit because it is both (i) not material and (ii) would be competitively harmful if publicly disclosed.

October 1, 2020 8-K

Entry into a Material Definitive Agreement - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 October 1, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-89

October 1, 2020 EX-2.1

Subscription and Purchase Agreement dated October 1, 2020 by and among Ark Insurance Holdings Limited, Bridge Holdings

wtm21exhibit Exhibit 2.1 Execution Version Certain identified confidential information contained in this document, marked by brackets, has been excluded from this exhibit because it is both (i) not material and (ii) would be competitively harmful if publicly disclosed. Ark Insurance Holdings Limited Subscription and Purchase Agreement CityPoint, 1 Ropemaker Street London, EC2Y 9AW TABLE OF CONTENT

August 7, 2020 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 August 7, 2020 Date of Report (Date of earliest event reported) WHITE MOUNTAINS INSURANCE GROUP, LTD. (Exact name of registrant as specified in its charter) Bermuda (State or other jurisdiction of incorporation or organization) 1-899

August 7, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the period ended June 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 1-8993 WHITE MOUNTAINS INSURANCE GROUP, LT

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