FORM10-Q☒QUARTERLY REPORT PURSUANT TO SECTION13 OR 15(d)OF THESECURITIES EXCHANGEACT OF 1934 For the period endedMarch 31, 2025 OR ☐TRANSITION REPORT PURSUANT TO SECTION13 OR 15(d)OF THESECURITIES EXCHANGEACT OF 1934 For the transition period fromtoCommission file number1-8993 WHITE MOUNTAINS INSURANCE GROUP,LTD. (Exact name of Registrant as specified in its charter) Securities registered pursuant to Section12(b)of the Act: Indicate by check mark whether the Registrant (1)has filed all reports required to be filed by Section13 or 15(d)of the SecuritiesExchange Act of 1934 during the preceding 12 months (or for such shorter period that the Registrant was required to file such reports), and(2)has been subject to such filing requirements for the past 90 days.YesýNo☐ Indicate by check mark whether the Registrant has submitted electronically every Interactive Data File required to be submitted pursuant toRule405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the Registrant wasrequired to submit such files).YesýNo☐ Indicate by check mark whether the Registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reportingcompany, or an emerging growth company.See the definitions of “large accelerated filer,” “accelerated filer”, “smaller reporting company”and “emerging growth company” in Rule12b-2 of the Exchange Act. Non-accelerated filer☐ If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complyingwith any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.o Indicate by check mark whether the Registrant is a shell company (as defined in Rule12b-2 of the Exchange Act). Yes☐Noý As of May 2, 2025,2,573,726common shares with a par value of $1.00 per share were outstanding (which includes 32,885 restrictedcommon shares that were not vested at such date). Table of Contents PARTI.FINANCIAL INFORMATIONItem 1.Financial Statements (Unaudited)Consolidated Balance Sheets,March 31, 2025andDecember 31, 20241Consolidated Statements of Operations and Comprehensive Income,Three Months Ended March 31, 2025 and 20243Consolidated Statements of Changes in Equity,Three Months Ended March 31, 2025 and 20246Consolidated Statements of Cash Flows,Three Months Ended March 31, 2025and20247Notes to Consolidated Financial Statements8Item 2.Management’s Discussion and Analysis of Financial Condition and Results of Operations47Results of Operations for theThree Months Ended March 31, 2025and202447Liquidity and Capital Resources67Non-GAAP Financial Measures70Critical Accounting Estimates72Forward-Looking Statements72Item 3.Quantitative and Qualitative Disclosures About Market Risk73Item 4.Controls and Procedures73PARTII.OTHER INFORMATION73Items 1 through 6.73 SIGNATURES WHITE MOUNTAINS INSURANCE GROUP,LTD.CONSOLIDATED STATEMENTS OF OPERATIONS(Unaudited) WHITE MOUNTAINS INSURANCE GROUP,LTD.CONSOLIDATED STATEMENTS OF OPERATIONS (CONTINUED)(Unaudited) WHITE MOUNTAINS INSURANCE GROUP,LTD.CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (LOSS)(Unaudited) Note 1.Basis of Presentation and Significant Accounting Policies Basis of Presentation White Mountains Insurance Group, Ltd. (the “Company” or the “Registrant”) is an exempted Bermuda limited liability company whoseprincipal businesses are conducted through its subsidiaries and other affiliates. The Company’s headquarters is located at 26 Reid Street,Hamilton, Bermuda HM11, its principal executive office is located at 23 South Main Street, Suite 3B, Hanover, New Hampshire 03755-2053and its registered office is located at Clarendon House, 2 Church Street, Hamilton, Bermuda HM 11. The Company’s website iswww.whitemountains.com. The information contained on White Mountains’s website is not incorporated by reference into, and is not a part of,this report.The accompanying consolidated financial statements have been prepared in accordance with generally accepted accounting principles in the United States (“GAAP”) and include the accounts of the Company, its subsidiaries (collectively with the Company, “White Mountains”)and other entities required to be consolidated under GAAP. Intercompany transactions have been eliminated in consolidation. Certain amountsin the prior period financial statements have been reclassified to conform to the current presentation.The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities as of the date of the financial statements and thereported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates.These interim financial statements include all adjustments considered necessary by management to fairly state the