Earnings release
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White Mountains INSURANCE GROUP Exhibit 99.1 CONTACT : Rob Seelig ( 603 ) 640-2212 WHITE MOUNTAINS REPORTS SECOND QUARTER RESULTS HAMILTON , Bermuda ( August 6 , 2026 ) - White Mountains Insurance Group , Ltd. ( NYSE : WTM ) reported book value per share of $ 2,258 as of June 30 , 2026 , an increase of 4 % for the second quarter of 2026 and 3 % for the first six months of 2026 , including dividends . Liam Caffrey , CEO , commented , “ Book value per share was up 4 % in the quarter , driven by strong operating company results and solid investment returns . Ark produced an 84 % combined ratio and strong growth in tangible book value . Kudu generated a 15 % return on equity on a trailing 12 months basis , driven by strong growth on a same store basis coupled with sale transactions . HG Global grew its book value by 1 % , including a $ 90 million dividend to White Mountains from its recent debt refinancing . Distinguished had a solid quarter , growing both managed premiums and ScaleCo adjusted EBITDA . MediaAlpha's share price increased 35 % in the quarter , producing $ 58 million of mark - to - market gains . Excluding MediaAlpha , the investment portfolio was up 2.8 % . We repurchased $ 191 million of shares in the quarter and deployed $ 132 million into two WTM Partners acquisitions . Factoring in other recent operating company distributions , undeployed capital now stands at roughly $ 0.8 billion . " Comprehensive income ( loss ) attributable to common shareholders was $ 199 million and $ 173 million in the second quarter and first six months of 2026 compared to $ 124 million and $ 159 million in the second quarter and first six months of 2025 . Results in the second quarter and first six months of 2026 included $ 151 million and $ 161 million of net realized and unrealized investment gains compared to $ 87 million and $ 173 million in the second quarter and first six months of 2025 . Results in the second quarter and first six months of 2026 also included $ 58 million and $ ( 7 ) million of unrealized investment gains ( losses ) from White Mountains's investment in MediaAlpha compared to $ 31 million and $ ( 6 ) million in the second quarter and first six months of 2025 . Ark / WM Outrigger The Ark / WM Outrigger segment's combined ratio was 84 % and 88 % in the second quarter and first six months of 2026 compared to 84 % and 90 % in the second quarter and first six months of 2025. Ark / WM Outrigger reported gross written premiums of $ 778 million and $ 1,868 million , net written premiums of $ 537 million and $ 1,128 million and net earned premiums of $ 376 million and $ 750 million in the second quarter and first six months of 2026 compared to gross written premiums of $ 815 million and $ 1,923 million , net written premiums of $ 579 million and $ 1,306 million and net earned premiums of $ 364 million and $ 722 million in the second quarter and first six months of 2025 . Ark's combined ratio was 84 % and 88 % in the second quarter and first six months of 2026 compared to 85 % and 90 % in the second quarter and first six months of 2025. Ark's combined ratio in the second quarter and first six months of 2026 included three points and five points of catastrophe losses , driven primarily by losses related to the war in Iran . This compares to minimal catastrophe losses in the second quarter of 2025 and thirteen points of catastrophe losses in the first six months of 2025 , driven by losses related to the California wildfires . Ark's combined ratio included eight points and six points of net favorable prior year development in the second quarter and first six months of 2026 , driven by the property and specialty lines of business . This compares to five points and nine points of net favorable prior year development in the second quarter and first six months of 2025 , driven primarily by the property , marine & energy and specialty lines of business . 1
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Ark has ongoing exposure to the war in Iran, primarily through the specialty and marine & energy lines of business. In the second quarter and first six months of 2026, Ark recorded estimated losses of $17 million and $42 million (net of reinsurance and reinstatement premiums) related to the war. Ark reported gross written premiums of $778 million and $1,868 million, net written premiums of $538 million and $1,128 million and net earned premiums of $375 million and $747 million in the second quarter and first six months of 2026 compared to gross written premiums of $815 million and $1,923 million, net written premiums of $536 million and $1,226 million and net earned premiums of $357 million and $703 million in the second quarter and first six months of 2025. The decline in gross written premiums in the second quarter of 2026 was driven primarily by softening market conditions in property lines, which was partially offset by growth in specialty lines. The decline in gross written premiums in the first six months of 2026 was driven primarily by a change in the timing of recognition of certain delegated authority business, which had no impact on the timing of recognition of Ark’s earned premiums. Ark reported pre-tax income of $78 million and $85 million in the second quarter and first six months of 2026 compared to $91 million and $144 million in the second quarter and first six months of 2025. Ark’s results included net realized and unrealized investment gains (losses) of $31 million and $(2) million in the second quarter and first six months of 2026 compared to $51 million and $81 million in the second quarter and first six months of 2025. Ark reported book value of $1,615 million as of June 30, 2026, an increase of 4% in the second quarter of 2026 and 5% in the first six months of 2026, including dividends. Ark reported tangible book value of $1,736 million as of June 30, 2026, an increase of 6% in the second quarter of 2026 and 7% in the first six months of 2026, including dividends. Ark’s book value includes goodwill and other intangible assets, net of tax, and White Mountains’s contingent consideration liability, which are excluded from Ark’s tangible book value. Ian Beaton, CEO of Ark, said, “Our results for the first half of the year have been good. Ark’s combined ratio was 84% for the second quarter and 88% year to date, and we grew tangible book value by 7% year to date. Gross premiums were down 5% in the quarter driven by rate softening in property lines, which offset solid growth in specialty lines. The Iran war losses to date have been manageable but uncertainty remains.” WM Outrigger Re’s combined ratio was 25% and 40% in the second quarter and first six months of 2026 compared to 44% and 120% in the second quarter and first six months of 2025. Catastrophe losses in the first six months of 2025 included $19 million of losses related to the California wildfires (net of reinstatement premiums). Kudu Kudu reported total revenues of $69 million, pre-tax income of $57 million and adjusted EBITDA of $16 million in the second quarter of 2026 compared to total revenues of $20 million, pre-tax income of $11 million and adjusted EBITDA of $16 million in the second quarter of 2025. Total revenues, pre-tax income and adjusted EBITDA included $19 million of net investment income in both the second quarter of 2026 and 2025. Total revenues and pre-tax income also included $50 million of net realized and unrealized investment gains in the second quarter of 2026 compared to $1 million in the second quarter of 2025. The increase in net realized and unrealized investment gains was driven by an increase in the fair value of Kudu’s participation contracts, primarily due to lower discount rates across the portfolio and step-ups in valuation related to certain sale transactions. On a trailing 12 months basis, return on equity was 15% as of June 30, 2026, up from 12% as of March 31, 2026, primarily due to higher net realized and unrealized investment gains. 2
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Kudu reported total revenues of $132 million, pre-tax income of $109 million and adjusted EBITDA of $33 million in the first six months of 2026 compared to total revenues of $84 million, pre-tax income of $64 million and adjusted EBITDA of $32 million in the first six months of 2025. Total revenues, pre-tax income and adjusted EBITDA included $40 million of net investment income in the first six months of 2026 compared to $39 million in the first six months of 2025. Total revenues and pre-tax income also included $92 million of net realized and unrealized investment gains in the first six months of 2026 compared to $45 million in the first six months of 2025. The increase in net realized and unrealized investment gains was driven by an increase in the fair value of Kudu’s participation contracts, primarily due to growth in assets under management at several managers, lower discount rates across the portfolio and step-ups in valuation related to certain sale transactions. Rob Jakacki, CEO of Kudu, said, “We delivered a strong second quarter and start to the year, generating a 4% return in the quarter and a 15% return on a trailing 12 months basis. Second quarter results were buoyed by a $20 million gain from a sale transaction. We also closed on two new investments in Australia during the first half of the year, further diversifying our portfolio. Our pipeline remains robust.” HG Global HG Global reported gross written premiums of $11 million and $19 million and earned premiums of $8 million and $15 million in the second quarter and first six months of 2026 compared to gross written premiums of $19 million and $26 million and earned premiums of $7 million and $15 million in the second quarter and first six months of 2025. HG Global’s total par value of policies assumed was $818 million and $1,335 million in the second quarter and first six months of 2026 compared to $931 million and $1,358 million in the second quarter and first six months of 2025. HG Global’s total gross pricing was 135 and 145 basis points in the second quarter and first six months of 2026 compared to 206 and 191 basis points in the second quarter and first six months of 2025. HG Global reported pre-tax income of $10 million and $21 million in the second quarter and first six months of 2026 compared to $17 million and $42 million in the second quarter and first six months of 2025. HG Global’s results included net realized and unrealized investment gains (losses) of $(2) million and $(7) million in the second quarter and first six months of 2026 compared to $3 million and $13 million in the second quarter and first six months of 2025, driven by movements in interest rates. The fair value of the BAM surplus notes increased to $353 million as of June 30, 2026 compared to $346 million as of March 31, 2026, resulting from $7 million of accrued interest. On July 28, 2026, HG Global received a cash payment of principal and interest on the BAM Surplus Notes of $8 million. On May 14, 2026, HG Global refinanced its senior debt facility, upsizing the facility to $200 million and lowering the interest rate to a fixed rate of 7.4%. In turn, on May 26, 2026, HG Global paid a $93 million cash dividend to shareholders, of which $90 million was paid to White Mountains. Kevin Pearson, President of HG Global, said, “HG Global had a slower second quarter, with a decline in gross written premiums, primarily due to continued tightening of municipal bond spreads and weaker primary market pricing. In the quarter, we refinanced our senior notes at improved terms and returned $93 million of capital to shareholders, enhancing our go-forward return profile.” We encourage you to read BAM’s second quarter statutory financial statements and operating supplement, which will be available on BAM’s website at https://bambonds.com/about-bam/credit-rating-and-financial-information/. 3
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Distinguished Distinguished reported managed premiums of $189 million and $321 million, commission and fee revenues of $57 million and $96 million, pre-tax loss of $11 million and $28 million and ScaleCo adjusted EBITDA of $12 million and $17 million for the second quarter and first six months of 2026. On a trailing 12 months basis, Distinguished reported managed premiums of $598 million and ScaleCo adjusted EBITDA of $28 million. These figures include periods prior to White Mountains’s ownership of Distinguished, which White Mountains believes is useful in understanding Distinguished’s performance. Jason Rotman, President of Distinguished, said “We had a solid second quarter. Trailing 12 months managed premiums and ScaleCo adjusted EBITDA were up 4% and 8% quarter-over-quarter. During the quarter, we enjoyed particularly strong growth in the environmental and urban real estate programs, partially offset by a decline in the umbrella program. Our newer growth programs are performing well, and we continue to add new teams and product lines to our GrowthCo vertical.” MediaAlpha As of June 30, 2026, White Mountains owned 17.9 million shares of MediaAlpha, representing a 29% basic ownership interest based on the total class A and class B common shares outstanding. As of June 30, 2026, MediaAlpha’s share price was $12.57 per share, which increased from $9.30 per share as of March 31, 2026. The carrying value of White Mountains’s investment in MediaAlpha was $225 million as of June 30, 2026 compared to $166 million as of March 31, 2026. At our June 30, 2026 level of ownership, each $1.00 per share increase or decrease in the share price of MediaAlpha will result in an approximate $7.50 per share increase or decrease in White Mountains’s book value per share. We encourage you to read MediaAlpha’s second quarter earnings release and related shareholder letter, which is available on MediaAlpha’s investor relations website at https://investors.mediaalpha.com. WTM Partners Beginning in the second quarter of 2026, in conjunction with the acquisitions of Basesix and Hawkeye Electric, WTM Partners has been presented as a separate reportable segment. Prior period amounts have been reclassified to conform to the current period presentation. WTM Partners reported total revenues of $93 million and $137 million, pre-tax income of $4 million and $2 million and adjusted EBITDA of $9 million and $11 million in the second quarter and first six months of 2026 compared to total revenues of $43 million and $43 million, pre-tax income (loss) of $1 million and $(2) million and adjusted EBITDA of $3 million and $2 million in the second quarter and first six months of 2025. The increases were driven by solid organic growth at Enterprise Solutions and the acquisitions of Basesix and Hawkeye Electric in the second quarter of 2026. John Daly, CEO and Managing Partner of WTM Partners, said “Enterprise Solutions had a solid quarter, generating the bulk of our $9 million of adjusted EBITDA. We closed two new deals in the quarter, including Basesix, a low voltage contracting platform, and Hawkeye Electric, a bolt-on to Enterprise Solutions, further diversifying our portfolio and footprint in the essential services sector. We have deployed roughly $200 million of equity capital and are working an active pipeline of new opportunities.” 4
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Other Operations White Mountains’s Other Operations reported pre-tax income (loss) of $115 million and $38 million in the second quarter and first six months of 2026 compared to $35 million and $(21) million in the second quarter and first six months of 2025. Net realized and unrealized investment gains were $72 million and $79 million in the second quarter and first six months of 2026 compared to $32 million and $35 million in the second quarter and first six months of 2025. Unrealized investment gains (losses) from White Mountains’s investment in MediaAlpha were $58 million and $(7) million in the second quarter and first six months of 2026 compared to $31 million and $(6) million in the second quarter and first six months of 2025. Net investment income was $16 million and $29 million in the second quarter and first six months of 2026 compared to $9 million and $18 million in the second quarter and first six months of 2025. White Mountains’s Other Operations reported general and administrative expenses of $43 million and $90 million in the second quarter and first six months of 2026 compared to $49 million and $104 million in the second quarter and first six months of 2025. The decrease in general and administrative expenses in the first six months of 2026 was driven primarily by lower loss and loss adjustment expenses in 2026 compared to 2025, which included losses related to the California wildfires, partially offset by higher incentive compensation costs due to an increase in White Mountains’s share price. Share Repurchases In the second quarter of 2026, White Mountains repurchased and retired 91,194 of its common shares for $191 million at an average share price of $2,092.72, or 93% of White Mountains’s June 30, 2026 book value per share. In the first six months of 2026, White Mountains repurchased and retired 103,816 of its common shares for $217 million at an average share price of $2,088.40, or 93% of White Mountains’s June 30, 2026 book value per share. Investments The total consolidated portfolio return was 3.5% in the second quarter of 2026. Excluding MediaAlpha, the total consolidated portfolio return was 2.8% in the second quarter of 2026. The total consolidated portfolio return was 2.7% in the second quarter of 2025. Excluding MediaAlpha, the total consolidated portfolio return was 2.3% in the second quarter of 2025. The total consolidated portfolio return was 3.7% in the first six months of 2026. Excluding MediaAlpha, the total consolidated portfolio return was 3.8% in the first six months of 2026. The total consolidated portfolio return was 4.5% in the first six months of 2025. Excluding MediaAlpha, the total consolidated portfolio return was 4.7% in the first six months of 2025. Mark Plourde, President of White Mountains Advisors, said, "Excluding MediaAlpha, the total portfolio returned 2.8% in the quarter. Our short duration fixed income portfolio returned 0.9%, ahead of the Bloomberg Intermediate Aggregate Index return of 0.5%. Excluding MediaAlpha, the equity portfolio returned 4.9%, behind the S&P 500 Index return of 15.2% in a strong up market for common stocks. Our equity results were impacted by lower relative returns from our market neutral positions and other long-term investments." Additional Information White Mountains is a Bermuda-domiciled financial services holding company traded on the New York Stock Exchange under the symbol WTM and the Bermuda Stock Exchange under the symbol WTM.BH. Additional financial information and other items of interest are available at the Company’s website located at www.whitemountains.com. White Mountains expects to file its Form 10-Q today with the Securities and Exchange Commission and urges shareholders to refer to that document for more complete information concerning its financial results. 5
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WHITE MOUNTAINS INSURANCE GROUP, LTD. CONDENSED CONSOLIDATED BALANCE SHEETS (millions)
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(Unaudited)
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June 30, 2026 December 31, 2025 June 30, 2025 Assets P&C Insurance and Reinsurance (Ark/WM Outrigger) Fixed maturity investments $ 2,011.9 $ 1,917.9 $ 1,755.8 Common equity securities 407.7 452.3 435.0 Short-term investments 536.9 866.6 611.4 Other long-term investments 769.0 689.7 609.1 Total investments 3,725.5 3,926.5 3,411.3 Cash (restricted $25.2, $1.1, $4.6) 91.5 104.8 162.7 Reinsurance recoverables 1,394.0 836.1 1,044.1 Insurance premiums receivable 1,473.2 848.4 1,451.4 Deferred acquisition costs 327.9 211.1 344.8 Goodwill and other intangible assets 292.5 292.5 292.5 Other assets 265.6 134.7 198.7 Total P&C Insurance and Reinsurance assets 7,570.2 6,354.1 6,905.5 Asset Management (Kudu) Short-term investments 114.4 21.9 42.3 Other long-term investments 1,344.6 1,291.4 1,127.2 Total investments 1,459.0 1,313.3 1,169.5 Cash 1.4 34.5 5.7 Accrued investment income 21.6 25.3 24.1 Goodwill and other intangible assets 7.6 7.7 7.8 Other assets 7.3 21.5 23.6 Total Asset Management assets 1,496.9 1,402.3 1,230.7 Financial Guarantee (HG Global) Fixed maturity investments 715.1 693.4 670.8 Short-term investments 34.2 90.8 42.9 Total investments 749.3 784.2 713.7 Cash .2 .1 9.2 BAM surplus notes, at fair value 352.8 339.0 396.7 Insurance premiums receivable 9.8 11.4 8.0 Deferred acquisition costs 98.5 96.9 90.4 Other assets 6.0 5.2 26.5 Total Financial Guarantee assets 1,216.6 1,236.8 1,244.5 Specialty Insurance Distribution (Distinguished) Short-term investments 79.4 94.0 — Total investments 79.4 94.0 — Cash (restricted $3.6, $0.1, $0.0) 4.1 2.7 — Premiums, commissions and fees receivable 69.8 45.7 — Goodwill and other intangible assets 565.1 577.7 — Other assets 26.4 15.3 — Total Specialty Insurance Distribution assets 744.8 735.4 — Services, Industrial and Consumer (WTM Partners) Short-term investments, at fair value .6 .5 .5 Total investments .6 .5 .5 Cash 6.1 4.4 5.3 Accounts receivable 78.8 39.5 37.7 Contract assets 36.3 17.8 15.1 Goodwill and other intangible assets 269.6 91.5 95.4 Other assets 43.5 28.7 29.6 Total Services, Industrial and Consumer assets 434.9 182.4 183.6 Other Operations Fixed maturity investments 312.9 159.2 170.0 Common equity securities 169.1 30.7 — Investment in MediaAlpha 224.5 231.2 195.5 Short-term investments 211.5 806.9 498.5 Other long-term investments 1,202.6 977.4 570.8 Total investments 2,120.6 2,205.4 1,434.8 Cash 24.2 38.4 36.2 Goodwill and other intangible assets 48.9 50.8 62.7 Other assets 104.3 95.9 97.0 Assets held for sale - Bamboo Group — — 620.7 Assets held for sale - Other 5.3 5.0 7.2 Total Other Operations assets 2,303.3 2,395.5 2,258.6 Total assets $ 13,766.7 $ 12,306.5 $ 11,822.9
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WHITE MOUNTAINS INSURANCE GROUP, LTD. CONDENSED CONSOLIDATED BALANCE SHEETS (CONTINUED) (millions) (Unaudited) June 30, 2026 December 31, 2025 June 30, 2025 Liabilities P&C Insurance and Reinsurance (Ark/WM Outrigger) Loss and loss adjustment expense reserves $ 2,623.8 $ 2,481.0 $ 2,288.5 Unearned insurance premiums 1,860.4 1,026.1 1,847.3 Debt 159.0 159.7 158.9 Reinsurance payable 642.8 286.2 463.8 Contingent consideration 370.0 328.3 193.4 Other liabilities 208.0 247.2 221.6 Total P&C Insurance and Reinsurance liabilities 5,864.0 4,528.5 5,173.5 Asset Management (Kudu) Debt 350.7 350.4 246.8 Other liabilities 116.7 96.5 82.4 Total Asset Management liabilities 467.4 446.9 329.2 Financial Guarantee (HG Global) Unearned insurance premiums 331.8 327.9 307.9 Debt 197.4 147.8 147.6 Other liabilities 20.1 23.8 32.8 Total Financial Guarantee liabilities 549.3 499.5 488.3 Specialty Insurance Distribution (Distinguished) Debt 140.9 140.8 — Premiums and commissions payable 114.0 81.3 — Other liabilities 77.3 85.0 — Total Specialty Insurance Distribution liabilities 332.2 307.1 — Services, Industrial and Consumer (WTM Partners) Debt 66.5 19.4 16.3 Contract liabilities 35.6 24.8 27.6 Other liabilities 81.2 47.2 46.5 Total Services, Industrial and Consumer liabilities 183.3 91.4 90.4 Other Operations Debt 18.0 18.9 20.4 Accrued incentive compensation 56.2 100.1 38.7 Other liabilities 40.3 55.4 54.6 Liabilities held for sale - Bamboo Group — — 281.2 Liabilities held for sale - Other 4.0 3.6 6.4 Total Other Operations liabilities 118.5 178.0 401.3 Total liabilities 7,514.7 6,051.4 6,482.7 Redeemable noncontrolling interests 131.5 131.5 — Equity White Mountains’s common shareholders’ equity White Mountains’s common shares and paid-in surplus 566.0 579.0 576.6 Retained earnings 4,821.0 4,845.6 4,067.6 Accumulated other comprehensive income (loss), after tax: Net unrealized gains (losses) from foreign currency translation 1.3 .8 .3 Total White Mountains’s common shareholders’ equity 5,388.3 5,425.4 4,644.5 Nonredeemable noncontrolling interests 732.2 698.2 695.7 Total equity 6,120.5 6,123.6 5,340.2 Total liabilities, redeemable noncontrolling interests and equity $ 13,766.7 $ 12,306.5 $ 11,822.9 7
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WHITE MOUNTAINS INSURANCE GROUP, LTD. BOOK VALUE PER SHARE (Unaudited) June 30, 2026 March 31, 2026 December 31, 2025 June 30, 2025 Book value per share numerator (in millions): White Mountains’s common shareholders’ equity $ 5,388.3 $ 5,373.5 $ 5,425.4 $ 4,644.5 Book value per share denominator (in thousands): Common shares outstanding 2,386.7 2,476.7 2,479.7 2,575.1 Book value per share $ 2,257.60 $ 2,169.66 $ 2,187.97 $ 1,803.57 Quarter-to-date change in book value per share,including dividends: 4.1 % (0.8)% 18.2 % 2.9 % Year-to-date change in book value per share,including dividends: 3.2 % (0.8)% 25.4 % 3.4 % Year-to-date dividends per share $ 1.00 $ 1.00 $ 1.00 $ 1.00 8
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WHITE MOUNTAINS INSURANCE GROUP, LTD. CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS (millions) (Unaudited) Three Months Ended June 30,Six Months Ended June 30, 2026 2025 2026 2025 Revenues: P&C Insurance and Reinsurance (Ark/WM Outrigger) Earned insurance premiums $ 376.2 $ 364.2 $ 750.0 $ 722.2 Net investment income 28.0 26.3 56.7 49.8 Net realized and unrealized investment gains (losses) 30.5 51.1 (2.4) 80.6 Other revenues 4.9 6.3 11.6 8.5 Total P&C Insurance and Reinsurance revenues 439.6 447.9 815.9 861.1 Asset Management (Kudu) Net investment income 19.0 19.3 39.8 38.7 Net realized and unrealized investment gains (losses) 49.7 .8 91.7 44.8 Other revenues .2 .3 .4 .7 Total Asset Management revenues 68.9 20.4 131.9 84.2 Financial Guarantee (HG Global) Earned insurance premiums 7.7 7.1 15.4 15.3 Net investment income 7.8 6.5 15.5 12.8 Net realized and unrealized investment gains (losses) (2.0) 3.1 (7.2) 13.1 Interest income from BAM surplus notes 6.9 7.5 13.8 15.0 Other revenues — — .1 .1 Total Financial Guarantee revenues 20.4 24.2 37.6 56.3 Specialty Insurance Distribution (Distinguished) Commission and fee revenues 56.6 — 96.2 — Other revenues .8 — 1.5 — Total Specialty Insurance Distribution revenues 57.4 — 97.7 — Services, Industrial and Consumer (WTM Partners) Product and service revenues 92.8 42.8 136.5 42.8 Total Services, Industrial and Consumer revenues 92.8 42.8 136.5 42.8 P&C Insurance Distribution (Bamboo) Commission and fee revenues — 59.1 — 103.3 Earned insurance premiums — 1.6 — 16.5 Other revenues — 1.8 — 4.1 Total P&C Insurance Distribution revenues — 62.5 — 123.9 Other Operations Net investment income 15.5 8.6 29.0 18.3 Net realized and unrealized investment gains (losses) 72.4 31.8 79.3 34.6 Net realized and unrealized investment gains (losses) from investment in MediaAlpha 58.4 30.5 (6.8) (6.1) Product and service revenues 14.7 13.5 27.5 27.1 Net gain on sale of the Bamboo Group — — 2.4 — Other revenues 4.5 7.0 11.4 24.8 Total Other Operations revenues 165.5 91.4 142.8 98.7 Total revenues $ 844.6 $ 689.2 $ 1,362.4 $ 1,267.0 9
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WHITE MOUNTAINS INSURANCE GROUP, LTD. CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS (CONTINUED) (millions) (Unaudited) Three Months Ended June 30,Six Months Ended June 30, 2026 2025 2026 2025 Expenses: P&C Insurance and Reinsurance (Ark/WM Outrigger) Loss and loss adjustment expenses $ 175.6 $ 164.0 $ 382.3 $ 397.5 Insurance acquisition expenses 103.7 97.2 202.5 180.7 General and administrative expenses 44.4 56.5 91.9 92.4 Change in fair value of contingent consideration 31.7 28.4 41.7 38.1 Interest expense 4.1 4.3 8.2 8.5 Total P&C Insurance and Reinsurance expenses 359.5 350.4 726.6 717.2 Asset Management (Kudu) General and administrative expenses 4.7 3.6 8.9 7.6 Interest expense 7.2 6.1 14.3 12.5 Total Asset Management expenses 11.9 9.7 23.2 20.1 Financial Guarantee (HG Global) Insurance acquisition expenses 2.1 2.0 4.2 3.9 General and administrative expenses 4.2 1.0 4.9 1.6 Interest expense 3.7 4.5 7.3 9.1 Total Financial Guarantee expenses 10.0 7.5 16.4 14.6 Specialty Insurance Distribution (Distinguished) Broker commission expenses 23.3 — 40.5 — General and administrative expenses 41.0 — 78.2 — Interest expense 3.6 — 7.1 — Total Specialty Insurance Distribution expenses 67.9 — 125.8 — Services, Industrial and Consumer (WTM Partners) Cost of sales 72.6 35.2 108.7 35.2 General and administrative expenses 15.5 6.4 25.3 9.4 Interest expense .6 .3 .9 .3 Total Service, Industrial and Consumer revenues 88.7 41.9 134.9 44.9 P&C Insurance Distribution (Bamboo) Broker commission expenses — 19.8 — 35.3 Loss and loss adjustment expenses — 1.7 — 12.6 Insurance acquisition expenses — (.6) — 6.0 General and administrative expenses — 22.6 — 42.6 Interest expense — 2.9 — 5.0 Total P&C Insurance Distribution expenses — 46.4 — 101.5 Other Operations Cost of sales 7.5 7.2 14.1 14.7 General and administrative expenses 42.5 49.1 89.6 104.1 Interest expense .6 .5 1.3 1.0 Total Other Operations expenses 50.6 56.8 105.0 119.8 Total expenses 588.6 512.7 1,131.9 1,018.1 Pre-tax income (loss) 256.0 176.5 230.5 248.9 Income tax (expense) benefit (24.8) (12.9) (25.6) (22.5) Net income (loss) 231.2 163.6 204.9 226.4 Net (income) loss attributable to noncontrollinginterests (31.7) (40.7) (32.6) (69.6) Net income (loss) attributable to White Mountains’scommon shareholders $ 199.5 $ 122.9 $ 172.3 $ 156.8
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WHITE MOUNTAINS INSURANCE GROUP, LTD. CONDENSED CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (LOSS) (millions) (Unaudited) Three Months Ended June 30,Six Months Ended June 30, 2026 2025 2026 2025 Net income (loss) attributable to White Mountains’scommon shareholders $ 199.5 $ 122.9 $ 172.3 $ 156.8 Other comprehensive income (loss), net of tax (.5) 1.1 .5 3.1 Comprehensive income (loss) 199.0 124.0 172.8 159.9 Other comprehensive (income) loss attributable tononcontrolling interests .4 (.3) — (1.1) Comprehensive income (loss) attributable to WhiteMountains’s common shareholders $ 199.4 $ 123.7 $ 172.8 $ 158.8 WHITE MOUNTAINS INSURANCE GROUP, LTD. EARNINGS PER SHARE (Unaudited) Earnings (loss) per share attributable to WhiteMountains’s common shareholders Three Months Ended June 30,Six Months Ended June 30, 2026 2025 2026 2025 Basic earnings (loss) per share $ 80.58 $ 47.75 $ 67.36 $ 60.99 Diluted earnings (loss) per share $ 80.58 $ 47.75 $ 67.36 $ 60.99 Dividends declared and paid per White Mountains’scommon share $ — $ — $ 1.00 $ 1.00 11
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WHITE MOUNTAINS INSURANCE GROUP, LTD. QTD SEGMENT STATEMENTS OF PRE-TAX INCOME (LOSS) (millions) (Unaudited) For the Three Months Ended June 30,2026 Ark/WM Outrigger Ark WMOutriggerRe Kudu HGGlobal DistinguishedWTMPartners OtherOperationsTotal Revenues: Earned insurance premiums $ 375.4 $ .8 $ — $ 7.7 $ — $ — $ .7 $ 384.6 Net investment income 26.9 1.1 19.0 7.8 .6 — 15.5 70.9 Net realized and unrealized investment gains (losses) 30.5 — 49.7 (2.0) — — 72.4 150.6 Net realized and unrealized investment gains (losses) from investment inMediaAlpha — — — — — — 58.4 58.4 Interest income from BAM surplus notes — — — 6.9 — — — 6.9 Commission and feerevenues — — — — 56.6 — 3.8 60.4 Product and servicesrevenues — — — — — 92.8 14.7 107.5 Other revenues 4.9 — .2 — .2 — — 5.3 Total revenues 437.7 1.9 68.9 20.4 57.4 92.8 165.5 844.6 Expenses: Loss and loss adjustmentexpenses 175.7 (.1) — — — — .1 175.7 Insurance acquisitionexpenses 103.4 .3 — 2.1 — — .3 106.1 Cost of sales — — — — — 72.6 7.5 80.1 Broker commission expenses — — — — 23.3 — — 23.3 Amortization of otherintangible assets — — — — 6.4 1.3 .9 8.6 General and administrativeexpenses 44.4 — 4.7 4.2 34.6 14.2 41.2 143.3 Change in fair value ofcontingent consideration 31.7 — — — — — — 31.7 Interest expense 4.1 — 7.2 3.7 3.6 .6 .6 19.8 Total expenses 359.3 .2 11.9 10.0 67.9 88.7 50.6 588.6 Pre-tax income (loss) $ 78.4 $ 1.7 $ 57.0 $ 10.4 $ (10.5) $ 4.1 $ 114.9 $ 256.0 Other Operations’s earned insurance premiums and commission and fee revenues are included in other revenues in the consolidated statement of operations. Distinguished’s net investment income is included in other revenues in the consolidated statement of operations. Other Operations’s loss and loss adjustment expenses and insurance acquisition expenses are included in general and administrative expenses in the consolidated statement of operations. Amortization of other intangible assets is included in general and administrative expenses in the consolidated statement of operations. Ark’s general and administrative expenses include $36.3 of other underwriting expenses. (1) (2) (1) (1) (2) (3) (3) (4) (3) (4) (5) (1) (2) (3) (4) (5) 12
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WHITE MOUNTAINS INSURANCE GROUP, LTD. QTD SEGMENT STATEMENTS OF PRE-TAX INCOME (LOSS) (CONTINUED) (millions) (Unaudited) For the Three Months Ended June 30,2025 Ark/WM Outrigger Ark WMOutriggerRe Kudu HGGlobal WTMPartners Bamboo OtherOperations Total Revenues: Earned insurance premiums $ 357.1 $ 7.1 $ — $ 7.1 $ — $ 1.6 $ 2.3 $ 375.2 Net investment income 24.1 2.2 19.3 6.5 — .7 8.6 61.4 Net realized and unrealized investment gains (losses) 51.1 — .8 3.1 — — 31.8 86.8 Net realized and unrealizedinvestment gains (losses) from investment inMediaAlpha — — — — — — 30.5 30.5 Interest income from BAM surplus notes — — — 7.5 — — — 7.5 Commission and fee revenues — — — — — 59.1 4.2 63.3 Product and servicesrevenues — — — — 42.8 — 13.5 56.3 Other revenues 6.3 — .3 — — 1.1 .5 8.2 Total revenues 438.6 9.3 20.4 24.2 42.8 62.5 91.4 689.2 Expenses: Loss and loss adjustmentexpenses 162.3 1.7 — — — 1.7 .8 166.5 Insurance acquisitionexpenses 95.8 1.4 — 2.0 — (.6) .9 99.5 Cost of sales — — — — 35.2 — 7.2 42.4 Broker commission expenses — — — — — 19.8 — 19.8 Amortization of otherintangible assets — — .1 — — 4.0 1.0 5.1 General and administrativeexpenses 56.5 — 3.5 1.0 6.4 18.6 46.4 132.4 Change in fair value ofcontingent consideration 28.4 — — — — — — 28.4 Interest expense 4.3 — 6.1 4.5 .3 2.9 .5 18.6 Total expenses 347.3 3.1 9.7 7.5 41.9 46.4 56.8 512.7 Pre-tax income (loss) $ 91.3 $ 6.2 $ 10.7 $ 16.7 $ .9 $ 16.1 $ 34.6 $ 176.5 Other Operations’s earned insurance premiums and commission and fee revenues are included in other revenues in the consolidated statement of operations. Bamboo’s net investment income is included in other revenues in the consolidated statement of operations. Other Operations’s loss and loss adjustment expenses and insurance acquisition expenses are included in general and administrative expenses in the consolidated statement of operations. Amortization of other intangible assets is included in general and administrative expenses in the consolidated statement of operations. Ark’s general and administrative expenses include $46.3 of other underwriting expenses. (1) (2) (1) (1) (2) (3) (3) (4) (3) (4) (5) (1) (2) (3) (4) (5) 13
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WHITE MOUNTAINS INSURANCE GROUP, LTD. YTD SEGMENT STATEMENTS OF PRE-TAX INCOME (LOSS) (millions) (Unaudited) For the Six Months Ended June 30,2026 Ark/WM Outrigger Ark WMOutriggerRe Kudu HGGlobal DistinguishedWTMPartners OtherOperationsTotal Revenues: Earned insurance premiums $ 746.5 $ 3.5 $ — $ 15.4 $ — $ — $ 4.1 $ 769.5 Net investment income 54.3 2.4 39.8 15.5 1.3 — 29.0 142.3 Net realized and unrealized investment gains (losses) (2.3) (.1) 91.7 (7.2) — — 79.3 161.4 Net realized and unrealized investment gains (losses) from investment inMediaAlpha — — — — — — (6.8) (6.8) Interest income from BAM surplus notes — — — 13.8 — — — 13.8 Commission and feerevenues — — — — 96.2 — 7.4 103.6 Product and servicesrevenues — — — — — 136.5 27.5 164.0 Net gain on sale of theBamboo Group — — — — — — 2.4 2.4 Other revenues 11.6 — .4 .1 .2 — (.1) 12.2 Total revenues 810.1 5.8 131.9 37.6 97.7 136.5 142.8 1,362.4 Expenses: Loss and loss adjustmentexpenses 382.1 .2 — — — — .4 382.7 Insurance acquisitionexpenses 201.3 1.2 — 4.2 — — 1.6 208.3 Cost of sales — — — — — 108.7 14.1 122.8 Broker commission expenses — — — — 40.5 — — 40.5 Amortization of otherintangible assets — — .1 — 13.8 2.5 1.9 18.3 General and administrativeexpenses 91.9 — 8.8 4.9 64.4 22.8 85.7 278.5 Change in fair value ofcontingent consideration 41.7 — — — — — — 41.7 Interest expense 8.2 — 14.3 7.3 7.1 .9 1.3 39.1 Total expenses 725.2 1.4 23.2 16.4 125.8 134.9 105.0 1,131.9 Pre-tax income (loss) $ 84.9 $ 4.4 $ 108.7 $ 21.2 $ (28.1) $ 1.6 $ 37.8 $ 230.5 Other Operations’s earned insurance premiums and commission and fee revenues are included in other revenues in the consolidated statement of operations. Distinguished’s net investment income is included in other revenues in the consolidated statement of operations. Other Operations’s loss and loss adjustment expenses and insurance acquisition expenses are included in general and administrative expenses in the consolidated statement of operations. Amortization of other intangible assets is included in general and administrative expenses in the consolidated statement of operations. Ark’s general and administrative expenses include $71.2 of other underwriting expenses. (1) (2) (1) (1) (2) (3) (3) (4) (3) (4) (5) (1) (2) (3) (4) (5)
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WHITE MOUNTAINS INSURANCE GROUP, LTD. YTD SEGMENT STATEMENTS OF PRE-TAX INCOME (LOSS) (CONTINUED) (millions) (Unaudited) For the Six Months Ended June 30,2025 Ark/WM Outrigger Ark WMOutriggerRe Kudu HGGlobal WTMPartnersBamboo OtherOperations Total Revenues: Earned insurance premiums $ 703.1 $ 19.1 $ — $ 15.3 $ — $ 16.5 $ 16.2 $ 770.2 Net investment income 45.4 4.4 38.7 12.8 — 1.4 18.3 121.0 Net realized and unrealized investment gains (losses) 80.7 (.1) 44.8 13.1 — .3 34.6 173.4 Net realized and unrealized investment gains (losses) from investment inMediaAlpha — — — — — — (6.1) (6.1) Interest income from BAM surplus notes — — — 15.0 — — — 15.0 Commission and fee revenues — — — — — 103.3 8.1 111.4 Product and services revenues — — — — 42.8 — 27.1 69.9 Other revenues 8.5 — .7 .1 — 2.4 .5 12.2 Total revenues 837.7 23.4 84.2 56.3 42.8 123.9 98.7 1,267.0 Expenses: Loss and loss adjustmentexpenses 375.6 21.9 — — — 12.6 18.2 428.3 Insurance acquisition expenses 179.6 1.1 — 3.9 — 6.0 6.0 196.6 Cost of sales — — — — 35.2 — 14.7 49.9 Broker commission expenses — — — — — 35.3 — 35.3 Amortization of other intangibleassets — — .2 — — 8.0 2.1 10.3 General and administrativeexpenses 92.3 .1 7.4 1.6 9.4 34.6 77.8 223.2 Change in fair value ofcontingent consideration 38.1 — — — — — — 38.1 Interest expense 8.5 — 12.5 9.1 .3 5.0 1.0 36.4 Total expenses 694.1 23.1 20.1 14.6 44.9 101.5 119.8 1,018.1 Pre-tax income (loss) $ 143.6 $ .3 $ 64.1 $ 41.7 $ (2.1) $ 22.4 $ (21.1) $ 248.9 Other Operations’s earned insurance premiums and commission and fee revenues are included in other revenues in the consolidated statement of operations. Bamboo’s net investment income and net realized and unrealized investment gains (losses) are included in other revenues in the consolidated statement of operations. Other Operations’s loss and loss adjustment expenses and insurance acquisition expenses are included in general and administrative expenses in the consolidated statement of operations. Amortization of other intangible assets is included in general and administrative expenses in the consolidated statement of operations. Ark’s general and administrative expenses include $74.8 of other underwriting expenses. (1) (2) (2) (1) (1) (2) (3) (3) (4) (3) (4) (5) (1) (2) (3) (4) (5) 15
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA ($ in millions) (Unaudited) Ark/WM Outrigger Three Months Ended June 30, 2026 Ark WMOutrigger ReElimination Total Insurance premiums: Gross written premiums $ 777.5 $ (.4) $ .4 $ 777.5 Net written premiums $ 537.8 $ (.4) $ — $ 537.4 Net earned premiums $ 375.4 $ .8 $ — $ 376.2 Insurance expenses: Loss and loss adjustment expenses $ 175.7 $ (.1) $ — $ 175.6 Insurance acquisition expenses 103.4 .3 — 103.7 Other underwriting expenses 36.3 — — 36.3 Total insurance expenses $ 315.4 $ .2 $ — $ 315.6 Insurance ratios: Loss and loss adjustment expenses 46.8 % (12.5)% — % 46.7 % Insurance acquisition expenses 27.5 37.5 — 27.6 Other underwriting expenses 9.7 — — 9.6 Combined Ratio 84.0 % 25.0 % — % 83.9 % Included within general and administrative expenses in the consolidated statement of operations. Ark/WM Outrigger Three Months Ended June 30, 2025 Ark WMOutrigger ReElimination Total Insurance premiums: Gross written premiums $ 815.2 $ 42.6 $ (42.6) $ 815.2 Net written premiums $ 536.0 $ 42.6 $ — $ 578.6 Net earned premiums $ 357.1 $ 7.1 $ — $ 364.2 Insurance expenses: Loss and loss adjustment expenses $ 162.3 $ 1.7 $ — $ 164.0 Insurance acquisition expenses 95.8 1.4 — 97.2 Other underwriting expenses 46.3 — — 46.3 Total insurance expenses $ 304.4 $ 3.1 $ — $ 307.5 Insurance ratios: Loss and loss adjustment expense 45.4 % 23.9 % — % 45.0 % Insurance acquisition expenses 26.8 19.8 — 26.7 Other underwriting expense 13.0 — — 12.7 Combined Ratio 85.2 % 43.7 % — % 84.4 % Included within general and administrative expenses in the consolidated statement of operations. (1) (1) (1) (1) 16
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) ($ in millions) (Unaudited) Ark/WM Outrigger Six Months Ended June 30, 2026 Ark WMOutrigger ReElimination Total Insurance premiums: Gross written premiums $ 1,868.4 $ (.4) $ .4 $ 1,868.4 Net written premiums $ 1,127.9 $ (.4) $ — $ 1,127.5 Net earned premiums $ 746.5 $ 3.5 $ — $ 750.0 Insurance expenses: Loss and loss adjustmentexpenses $ 382.1 $ .2 $ — $ 382.3 Insurance acquisition expenses 201.3 1.2 — 202.5 Other underwriting expenses 71.2 — — 71.2 Total insurance expenses $ 654.6 $ 1.4 $ — $ 656.0 Insurance ratios: Loss and loss adjustment expense 51.2 % 5.7 % — % 51.0 % Insurance acquisition expenses 27.0 34.3 — 27.0 Other underwriting expense 9.5 — — 9.5 Combined Ratio 87.7 % 40.0 % — % 87.5 % Included within general and administrative expenses in the consolidated statement of operations. Ark/WM Outrigger Six Months Ended June 30, 2025 Ark WMOutrigger ReElimination Total Insurance premiums: Gross written premiums $ 1,922.8 $ 80.1 $ (80.1) $ 1,922.8 Net written premiums $ 1,226.2 $ 80.1 $ — $ 1,306.3 Net earned premiums $ 703.1 $ 19.1 $ — $ 722.2 Insurance expenses: Loss and loss adjustmentexpenses $ 375.6 $ 21.9 $ — $ 397.5 Insurance acquisition expenses 179.6 1.1 — 180.7 Other underwriting expenses 74.8 — — 74.8 Total insurance expenses $ 630.0 $ 23.0 $ — $ 653.0 Insurance ratios: Loss and loss adjustment expense 53.4 % 114.7 % — % 55.0 % Insurance acquisition expenses 25.5 5.7 — 25.0 Other underwriting expense 10.6 — — 10.4 Combined Ratio 89.5 % 120.4 % — % 90.4 % Included within general and administrative expenses in the consolidated statement of operations. (1) (1) (1) (1) 17
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) ($ in millions) (Unaudited) Kudu Three MonthsEnded June 30,2025 Three MonthsEnded June 30,2026 Six MonthsEnded June 30,2025 Six MonthsEnded June 30,2026 Twelve MonthsEnded June 30,2026 Net investment income $ 19.3 $ 19.0 $ 38.7 $ 39.8 $ 79.8 Net realized and unrealized investment gains(losses) .8 49.7 44.8 91.7 150.4 Other revenues .3 .2 .7 .4 .9 Total revenues 20.4 68.9 84.2 131.9 231.1 General and administrative expenses 3.6 4.7 7.6 8.9 19.2 Interest expense 6.1 7.2 12.5 14.3 27.7 Total expenses 9.7 11.9 20.1 23.2 46.9 GAAP pre-tax income (loss) 10.7 57.0 64.1 108.7 184.2 Income tax (expense) benefit 1.0 (15.0) (10.6) (28.8) (42.4) GAAP net income (loss) 11.7 42.0 53.5 79.9 141.8 Add back: Interest expense 6.1 7.2 12.5 14.3 27.7 Income tax expense (benefit) (1.0) 15.0 10.6 28.8 42.4 Depreciation — .1 — .1 .3 Amortization of other intangible assets .1 — .2 .1 .2 EBITDA 16.9 64.3 76.8 123.2 212.4 Exclude: Net realized and unrealized investment (gains)losses (.8) (49.7) (44.8) (91.7) (150.4) Non-cash equity-based compensationexpense — — — — .5 Transaction expenses .1 1.1 — 1.1 3.0 Adjusted EBITDA $ 16.2 $ 15.7 $ 32.0 $ 32.6 $ 65.5 Adjustment to annualize partial year revenues from participation contracts acquired 5.3 Adjustment to remove partial year revenues from participation contracts sold (2.3) Annualized adjusted EBITDA $ 68.5 GAAP net investment income $ 79.8 Adjustment to annualize partial year revenues from participation contracts acquired 5.3 Adjustment to remove partial year revenues from participation contracts sold (2.3) Annualized revenue $ 82.8 Net equity capital drawn $ 484.4 Debt capital drawn 358.3 Total net capital drawn and invested $ 842.7 GAAP net investment income revenue yield 9.5% Cash revenue yield 9.8% Return on equity 14.7% Net investment income includes revenues from participation contracts and income from short-term and other long-term investments. Total net capital drawn represents equity and debt capital drawn and invested less cumulative distributions. Return on equity is calculated based on the GAAP net income (loss) divided by the average of Kudu’s beginning and ending GAAP equity. (1) (1) (2) (3) (1) (2) (3) 18
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) (millions) (Unaudited) Three Months Ended June 30,Six Months Ended June 30, Kudu 2026 2025 2026 2025 Beginning balance of Kudu’s participation contracts $ 1,352.2 $ 1,120.4 $ 1,285.0 $ 1,008.4 Contributions to participation contracts 17.9 .2 43.3 68.2 Proceeds from participation contracts sold (75.1) — (75.1) — Net realized and unrealized investment gains (losses)on participation contracts sold and pending sale 26.2 9.1 26.5 9.1 Net unrealized investment gains (losses) onparticipation contracts - all other 23.4 (8.6) 64.9 35.4 Ending balance of Kudu’s participation contracts $ 1,344.6 $ 1,121.1 $ 1,344.6 $ 1,121.1 As of March 31, 2026, March 31, 2025, December 31, 2025 and 2024, Kudu’s other long-term investments also include $6.6, $5.8, $6.4 and $5.6 related to a private debt instrument. Includes contributions to new and existing participation contracts. Includes $3.5 of non-cash contributions to (proceeds from) participation contracts for the three and six months ended June 30, 2026. Includes net realized and unrealized investment gains (losses) recognized from participation contracts beginning in the quarter a contract is classified as pending sale. Includes net unrealized investment gains (losses) recognized from (i) ongoing participation contracts and (ii) participation contracts prior to classification as pending sale. As of June 30, 2025, Kudu’s other long-term investments also include $6.1 related to a private debt instrument. (1) (2)(3) (3) (4) (5) (6) (1) (2) (3) (4) (5) (6) 19
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) ($ in millions) (Unaudited) Three Months Ended June 30, Six Months Ended June 30, HG Global 2026 2025 2026 2025 Par value assumed: Par value of primary market policies assumed $ 741.0 $ 840.1 $ 1,159.4 $ 1,167.1 Par value of secondary market policies assumed 76.6 90.4 175.8 190.7 Total par value of policies assumed $ 817.6 $ 930.5 $ 1,335.2 $ 1,357.8 Reinsurance premiums: Gross written premiums from primary market $ 8.9 $ 16.7 $ 13.0 $ 20.5 Gross written premiums from secondary market 2.1 2.5 6.3 5.4 Total gross written premiums 11.0 19.2 19.3 25.9 Ceding commission paid 3.2 5.8 5.7 7.8 Total gross written premiums net of cedingcommission paid $ 7.8 $ 13.4 $ 13.6 $ 18.1 Earned premiums $ 7.7 $ 7.1 $ 15.4 $ 15.3 Pricing: Gross pricing from primary market 120 bps 199 bps 112 bps 176 bps Gross pricing from secondary market 274 bps 277 bps 358 bps 283 bps Total gross pricing 135 bps 206 bps 145 bps 191 bps Total pricing net of ceding commission paid 95 bps 144 bps 102 bps 133 bps For capital appreciation bonds, par is adjusted to the estimated equivalent par value for current interest paying bonds. HG Global As ofJune 30, 2026 As ofDecember 31, 2025 As ofJune 30, 2025 Unearned premiums $ 331.8 $ 327.9 $ 307.9 Deferred acquisition costs 98.5 96.9 90.4 Unearned premiums, net of deferred acquisition costs $ 233.3 $ 231.0 $ 217.5 (1) (1) (1) 20
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) (millions) (Unaudited) Distinguished Three Months EndedJune 30, 2026 Six Months Ended June 30, 2026 Commission and fee revenues $ 56.6 $ 96.2 Other revenues .8 1.5 Total revenues 57.4 97.7 Broker commission expenses 23.3 40.5 General and administrative expenses 41.0 78.2 Interest expense 3.6 7.1 Total expenses 67.9 125.8 GAAP pre-tax income (loss) (10.5) (28.1) Income tax (expense) benefit .7 3.9 GAAP net income (loss) (9.8) (24.2) Exclude: Net (income) loss, GrowthCo 10.4 18.2 ScaleCo net income (loss) .6 (6.0) Add back: Interest expense 3.6 7.1 Income tax expense (benefit) (.7) (3.9) Depreciation .1 .2 Amortization of other intangible assets 6.4 13.8 ScaleCo EBITDA 10.0 11.2 Exclude: Non-cash equity-based compensation expense 2.3 4.7 Restructuring expenses — .8 Legal settlement expenses .1 .1 ScaleCo adjusted EBITDA $ 12.4 $ 16.8 21
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WHITE MOUNTAINS INSURANCE GROUP, LTD. SELECTED FINANCIAL DATA (CONTINUED) (millions) (Unaudited) WTM Partners Three MonthsEnded June 30,2025 Three MonthsEnded June 30,2026 Six MonthsEnded June 30,2025 Six MonthsEnded June 30,2026 Twelve MonthsEnded June 30,2026 Product and service revenues $ 42.8 $ 92.8 $ 42.8 $ 136.5 $ 237.8 Total revenues 42.8 92.8 42.8 136.5 237.8 Cost of sales 35.2 72.6 35.2 108.7 194.6 General and administrative expenses 6.4 15.5 9.4 25.3 40.8 Interest expense .3 .6 .3 .9 1.5 Total expenses 41.9 88.7 44.9 134.9 236.9 GAAP pre-tax income (loss) .9 4.1 (2.1) 1.6 .9 Income tax (expense) benefit .2 (.6) .2 (.7) (1.0) GAAP net income (loss) 1.1 3.5 (1.9) .9 (.1) Add back: Interest expense .3 .6 .3 .9 1.5 Income tax expense (benefit) (.2) .6 (.2) .7 1.0 Depreciation .3 .5 .3 .8 1.4 Amortization of other intangible assets — 1.3 — 2.5 6.2 EBITDA 1.5 6.5 (1.5) 5.8 10.0 Exclude: Transaction expenses 1.2 2.6 3.0 4.6 5.0 Restructuring and integration expenses — .1 — .1 .1 Adjusted EBITDA $ 2.7 $ 9.2 $ 1.5 $ 10.5 $ 15.1 Includes results for periods subsequent to the acquisitions of Enterprise Solutions on April 1, 2025, Basesix on April 1, 2026 and Hawkeye Electric on May 1, 2026. (1) (1) 22
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Regulation G This earnings release includes non-GAAP financial measures that have been reconciled from their most comparable GAAP financial measures. • Ark’s tangible book value and growth in tangible book value are non-GAAP financial measures. Tangible book value is a non-GAAP financial measure derived by adjusting GAAP book value to exclude (i) goodwill and other intangible assets, (ii) the deferred tax liability on other intangible assets and (iii) the contingent consideration liability. The contingent consideration liability represents the estimated fair value of the additional shares that could be earned by management rollover shareholders if and to the extent that White Mountains achieves certain multiple of invested capital return thresholds. If earned, these additional shares would result in a reallocation of economics among Ark’s shareholders, which is reflected in the fair value of the contingent consideration liability recorded by White Mountains, but would have no impact on Ark’s stand-alone book value or tangible book value. Growth in tangible book value equals the change in tangible book value plus dividends for the period divided by beginning tangible book value. White Mountains believes that these non-GAAP financial measures are useful to management and investors in evaluating Ark’s enterprise value. The following table presents the reconciliation of Ark’s GAAP equity to tangible book value. $ in millions June 30,2026 March 31,2026 December 31,2025 Ark’s GAAP book value $ 1,615.0 $ 1,547.1 $ 1,593.9 Less: goodwill and other intangible assets, net (248.6) (248.6) (248.6) Plus: contingent consideration 370.0 338.3 328.3 Ark’s tangible book value $ 1,736.4 $ 1,636.8 $ 1,673.6 Year-to-date dividends declared $ 50.5 $ 50.5 $ 41.5 Quarter-to-date growth in GAAP book value, including dividends: 4.4 % 0.2 % (2.1)% Quarter-to-date growth in tangible book value, including dividends: 6.1 % 0.8 % 4.0 % Year-to-date growth in GAAP book value, including dividends: 4.5 % 0.2 % 13.7 % Year-to-date growth in tangible book value, including dividends: 6.8 % 0.8 % 27.6 % Amounts are net of deferred tax liabilities related to other intangible assets of $43.9. • Kudu’s EBITDA, adjusted EBITDA, annualized adjusted EBITDA, annualized revenue and cash revenue yield are non-GAAP financial measures. EBITDA is a non-GAAP financial measure that adds back interest expense on debt, income tax (expense) benefit, depreciation and amortization of other intangible assets to GAAP net income (loss). (1) (1) 23
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Adjusted EBITDA is a non-GAAP financial measure that excludes certain other items in GAAP net income (loss) in addition to those added back to calculate EBITDA. The items relate to (i) net realized and unrealized investment gains (losses) on Kudu’s revenue and earnings participation contracts, (ii) non-cash equity-based compensation expense and (iii) transaction expenses. A description of each item follows: • Net realized and unrealized investment gains (losses) - Represents net unrealized investment gains and losses recorded on Kudu’s revenue and earnings participation contracts, which are recorded at fair value under GAAP, and realized investment gains and losses from participation contracts sold during the period. • Non-cash equity-based compensation expense - Represents non-cash expenses related to Kudu’s management compensation that are settled with equity units in Kudu. • Transaction expenses - Represents costs directly related to Kudu’s mergers and acquisitions activity, such as external lawyer, banker, consulting and placement agent fees, which are not capitalized and are expensed under GAAP. Annualized adjusted EBITDA is a non-GAAP financial measure that (i) annualizes partial year revenues related to Kudu’s revenue and earnings participation contracts acquired during the previous 12-month period and (ii) removes partial year revenues related to revenue and earnings participation contracts sold during the previous 12-month period. Annualized revenue is a non-GAAP financial measure that adds the adjustments for annualized adjusted EBITDA to GAAP net investment income. Cash revenue yield is a non-GAAP financial measure that is derived using annualized revenue as a percentage of total net capital drawn and invested. The most directly comparable GAAP financial measure is net investment income revenue yield, which is derived using GAAP net investment income as a percentage of total net capital drawn and invested. White Mountains believes that these non-GAAP financial measures are useful to management and investors in evaluating Kudu’s underlying performance. White Mountains also believes that annualized adjusted EBITDA is useful to management and investors in understanding the full earnings profile of Kudu’s business as of the end of any 12-month period. See page 18 for the reconciliation of Kudu’s GAAP net income (loss) to EBITDA, adjusted EBITDA and annualized adjusted EBITDA, and the reconciliation of Kudu’s GAAP net investment income to annualized revenue. • Distinguished’s ScaleCo net income (loss), ScaleCo EBITDA and ScaleCo adjusted EBITDA are non-GAAP financial measures. ScaleCo net income (loss) is a non-GAAP financial measure that excludes the results of the GrowthCo vertical, which is consolidated under GAAP, from Distinguished’s consolidated GAAP net income (loss). ScaleCo EBITDA is a non-GAAP financial measure that adds back interest expense on debt, income tax (expense) benefit, depreciation and amortization of other intangible assets to ScaleCo net income (loss). ScaleCo adjusted EBITDA is a non-GAAP financial measure that excludes certain other items in GAAP net income (loss) in addition to those items added back to calculate ScaleCo EBITDA. The items relate to (i) non-cash equity- based compensation expense, (ii) restructuring expenses and (iii) legal settlement expenses. A description of each item follows: • Non-cash equity-based compensation expense - Represents non-cash expenses related to Distinguished’s management compensation that are settled with equity units in Distinguished. 24
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• Restructuring expenses - Represents costs related to Distinguished’s corporate restructuring and capital planning activities. • Legal settlement expenses - Represents amounts incurred related to legal settlements. White Mountains believes that these non-GAAP financial measures are useful to management and investors in evaluating Distinguished’s underlying performance. White Mountains also believes that excluding the results of the GrowthCo vertical, which Distinguished views as an investment in start-up programs, is useful to understanding the underlying performance of Distinguished’s established programs. See page 21 for the reconciliation of Distinguished’s consolidated GAAP net income (loss) to ScaleCo net income (loss), ScaleCo EBITDA and ScaleCo adjusted EBITDA. • WTM Partners’s EBITDA and adjusted EBITDA are non-GAAP financial measures. EBITDA is a non-GAAP financial measure that adds back interest expense on debt, income tax (expense) benefit, depreciation and amortization of other intangible assets to GAAP net income (loss). Adjusted EBITDA is a non-GAAP financial measure that excludes certain other items in GAAP net income (loss) in addition to those added back to calculate EBITDA. The items relate to (i) transaction expenses and (ii) restructuring and integration expenses. A description of each item follows: • Transaction expenses - Represents costs directly related to WTM Partners’s mergers and acquisitions activity, such as external lawyer, banker, consulting and placement agent fees, which are not capitalized and are expensed under GAAP. • Restructuring and integration expenses - Represents costs related to WTM Partners’s corporate restructuring and mergers and acquisitions integration activities. White Mountains believes that these non-GAAP financial measures are useful to management and investors in evaluating WTM Partners’s underlying performance. See page 22 for the reconciliation of WTM Partners’s GAAP net income (loss) to EBITDA and adjusted EBITDA. • Total consolidated portfolio return excluding MediaAlpha and total equity portfolio return excluding MediaAlpha are non-GAAP financial measures that remove the net investment income and net realized and unrealized investment gains (losses) from White Mountains’s investment in MediaAlpha. White Mountains believes these measures to be useful to management and investors by showing the underlying performance of White Mountains’s investment portfolio and equity portfolio without regard to White Mountains’s investment in MediaAlpha. The following tables present reconciliations from GAAP to the reported percentages: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 Total consolidated portfolio return 3.5 % 2.7 % 3.7 % 4.5 % Remove MediaAlpha (0.7) (0.4) 0.1 0.2 Total consolidated portfolio return excluding MediaAlpha 2.8 % 2.3 % 3.8 % 4.7 % Three Months Ended June30, 2026 Total equity portfolio return 6.1 % Remove MediaAlpha (1.2) Total equity portfolio return excluding MediaAlpha 4.9 % 25
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Safe Harbor Statement under the Private Securities Litigation Reform Act of 1995 This earnings release 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 release which address activities, events or developments which White Mountains expects or anticipates will or may occur in the future are forward-looking statements. The words “may,” “could,” “will,” “believe,” “intend,” “expect,” “anticipate,” “project,” “estimate,” “predict” and similar expressions are also intended to identify forward- looking statements. These forward-looking statements include, among others, statements with respect to White Mountains’s: • change in book value per share or return on equity; • business strategy; • financial and operating targets or plans; • incurred loss and loss adjustment expenses and the adequacy of its loss and loss adjustment expense reserves and related reinsurance; • projections of revenues, income (or loss), earnings (or loss) per share, EBITDA, adjusted EBITDA, dividends, market share or other financial forecasts of White Mountains or its businesses; • expansion and growth of its business and operations; and • future capital expenditures. These statements are based on certain assumptions and analyses made by White Mountains in light of its experience and perception of historical trends, current conditions and expected future developments, as well as other factors believed to be appropriate in the circumstances. However, whether actual results and developments will conform to its expectations and predictions is subject to risks and uncertainties that could cause actual results to differ materially from expectations, including: • the risks that are described from time to time in White Mountains’s filings with the Securities and Exchange Commission, including but not limited to White Mountains’s 2025 Annual Report on Form 10-K; • claims arising from catastrophic events, such as hurricanes, windstorms, earthquakes, floods, wildfires, tornadoes, tsunamis, severe weather, public health crises, terrorist attacks, war and war-like actions, explosions, infrastructure failures or cyber attacks; • recorded loss reserves subsequently proving to have been inadequate; • the market value of White Mountains’s investment in MediaAlpha; • business opportunities (or lack thereof) that may be presented to it and pursued; • actions taken by rating agencies, such as financial strength or credit ratings downgrades or placing ratings on negative watch; • the continued availability of capital and financing; • the continued availability of fronting and reinsurance capacity; • deterioration of general economic, market or business conditions, including due to war and war-like actions and outbreaks of contagious disease and corresponding mitigation efforts; • competitive forces, including the conduct of other insurers; • changes in domestic or foreign laws or regulations, or their interpretation, applicable to White Mountains, its competitors or its customers; and • other factors, most of which are beyond White Mountains’s control. Consequently, all of the forward-looking statements made in this earnings release are qualified by these cautionary statements, and there can be no assurance that the actual results or developments anticipated by White Mountains will be realized or, even if substantially realized, that they will have the expected consequences to, or effects on, White Mountains or its business or operations. White Mountains assumes no obligation to publicly update any such forward-looking statements, whether as a result of new information, future events or otherwise. 26