WHITE MOUNTAINS INSURANCE GROUP LTD

OTHER OPERATIONS

White Mountains’s Other Operations consists of the Company and its wholly-owned subsidiary, WM Capital, its other intermediate holding companies, its wholly-owned investment management subsidiary, WM Advisors, investment assets managed by WM Advisors, its interests in the Bamboo SPV, MediaAlpha, PassportCard/DavidShield, BroadStreet, Elementum, WTM Partners, Enterprise Solutions, the Bamboo CRVs, Other Operating Businesses and certain other assets.

WM Advisors

As of December 31, 2025, WM Advisors managed and/or provided oversight and administration for substantially all of White Mountains’s fixed maturity investments, short-term investments, common equity securities and other long-term investments.

Bamboo

On January 2, 2024, White Mountains acquired a controlling financial interest in Bamboo. On December 5, 2025, White Mountains completed the sale of a controlling financial interest in WM Pierce Holdings, Inc. and its subsidiaries, including Bamboo MGA (collectively, the "Bamboo Group"), to affiliates of funds advised by CVC Capital Partners (“CVC”), pursuant to the terms of the securities purchase agreement dated October 2, 2025 (the "Bamboo SPA"). Under the terms of the Bamboo SPA, White Mountains sold approximately 77.3% of its equity interest in Bamboo for net cash proceeds at closing of $848 million and retained an indirect equity interest valued at $250 million (the “Bamboo Sale Transaction”). White Mountains’s indirect equity interest is held through the Bamboo SPV. See Note 2 — “Significant Transactions” on page F-19.

As a result of the Bamboo Sale Transaction, White Mountains deconsolidated the Bamboo Group on December 5, 2025, and Bamboo is no longer a reportable segment. Through December 5, 2025, Bamboo’s results of operations are presented within the Bamboo segment. White Mountains’s noncontrolling equity interest in the Bamboo SPV is accounted for at fair value in other long-term investments within Other Operations. The Bamboo Group’s assets and liabilities have been presented as held for sale as of December 31, 2024. See Note 20 — “Held for Sale” on page F-79.

Bamboo is a capital-light, tech- and data-enabled insurance distribution platform providing homeowners’ insurance and related products to the residential property market in California and, beginning in the third quarter of 2025, in Texas. Bamboo operates primarily through Bamboo MGA, its full-service MGA business, where the company manages all aspects of the placement process on behalf of its fronting and reinsurance carrier partners (“Capacity Providers”), including product development, marketing, underwriting, policy issuance and claims oversight, and it earns commissions based on the volume and profitability of the insurance that it places. Bamboo MGA offers both admitted and non-admitted products. Under its capacity agreements, Bamboo MGA’s commission levels are based on a sliding scale tied primarily to its attritional loss ratio. Bamboo also operates two separate but integrated businesses: (i) a retail agency, within Bamboo MGA, offering ancillary products (e.g., flood, earthquake) on behalf of third parties and (ii) Ide8 Re, Inc. (the “Bamboo Captive”), a U.S.-domiciled captive reinsurer that participates in the underwriting risk of Bamboo’s MGA programs to align interests with Capacity Providers.

As of December 31, 2025, White Mountains had a 27.9% limited partnership interest in the Bamboo SPV. As of December 31, 2025, White Mountains owned 17.2% of the basic units outstanding of Bamboo (14.6% on a fully-diluted/fully-converted basis, taking account of management’s equity incentives) on a look-through basis. As of December 31, 2025, the fair value of White Mountains’s interest in the Bamboo SPV was $250 million.

MediaAlpha

MediaAlpha is a marketing technology company. It operates a transparent and efficient customer acquisition technology platform that facilitates real-time transactions between buyers and sellers of consumer referrals (i.e., clicks, calls and leads), primarily in the property & casualty, health and life insurance verticals. MediaAlpha generates revenue by earning a fee for each consumer referral sold on its platform. A transaction becomes payable only on a qualifying consumer action, and is not contingent on the sale of a product to the consumer.

White Mountains’s investment in MediaAlpha is accounted for at fair value based on the publicly traded share price of MediaAlpha’s common stock and is presented as a separate line item on the balance sheet.

During the second quarter of 2024, MediaAlpha completed a secondary offering of 7.6 million shares at $19.00 per share ($18.24 per share net of underwriting fees). In the secondary offering, White Mountains sold 5.0 million shares for net proceeds of $91.2 million. During the second quarter of 2023, White Mountains completed a tender offer to purchase 5.9 million additional shares of MediaAlpha at a purchase price of $10.00 per share.

As of December 31, 2025, White Mountains owned 17.9 million shares of MediaAlpha, representing a 27.4% basic ownership interest based on the total class A and class B common shares outstanding in MediaAlpha’s Report on Form 10-Q dated October 29, 2025. At the December 31, 2025 share price of $12.95, the fair value of White Mountains’s investment in MediaAlpha was $231 million. As of December 31, 2024, White Mountains owned 17.9 million shares of MediaAlpha, representing a 26.6% basic ownership interest. At the December 31, 2024 share price of $11.29, the fair value of White Mountains’s investment in MediaAlpha was $202 million.

PassportCard/DavidShield is an international MGA specializing in leisure travel insurance and global expatriate medical insurance. PassportCard/DavidShield delivers digitally-enabled insurance solutions that provide real time funding for covered medical expenses at the point of care.

PassportCard/DavidShield writes two principal product lines: (i) leisure travel insurance (“PassportCard”) and (ii) comprehensive expatriate medical services (“DavidShield”). PassportCard/DavidShield offers these products to both individuals and organizations. Its principal markets include Israel (its home market) as well as the European Union and Australia – servicing over two million insured members in over 180 countries. In Israel, PassportCard/DavidShield operates through a wholly-owned insurance carrier that underwrites policies and cedes substantially all underwriting risk to its highly-rated reinsurance partners. Outside Israel, PassportCard/DavidShield places policies with licensed third-party insurance carriers. PassportCard/DavidShield earns commissions for the placement of policies with its insurance and reinsurance carrier partners and licensing fees for the use of its card-based technology. PassportCard/DavidShield distributes its products through brokers, strategic partnerships and direct-to-consumer digital channels.

There are a number of distinct advantages to the PassportCard/DavidShield insurance solutions that differentiate its business in the marketplace. PassportCard/DavidShield offers its members a proprietary, card-based platform that enables paperless claims processing and immediate payment authorization, reducing reliance on traditional reimbursement models. This technology-driven approach supports enhanced claims control, fraud mitigation and data-informed loss management, thereby contributing to competitive loss ratios for its reinsurance partners and a differentiated customer experience.

By leveraging the regulated payment capabilities and propriety infrastructure of a debit card model, PassportCard/DavidShield has been able to integrate its insurance services with personal travel-related payment functionality. In July 2025, PassportCard/DavidShield launched an integrated Travel Money Payment Card, a solution combining the insurance claims card with a personal travel-focused payment card that enables customers to manage both medical expenses and personal travel spending through the same card.

As a business based in Israel, PassportCard/DavidShield has been affected by the geopolitical environment in the Middle East. Following the events of October 7, 2023 and the resulting war in Gaza, PassportCard/DavidShield experienced a significant decline in revenues relating to its Israeli leisure travel segment. However, Israeli leisure travel revenues placed by PassportCard have gradually recovered and have now surpassed pre-war levels despite intermittent periods of increased geopolitical unrest in the region and reduced capacity from international airline carriers offering service to and from Israel. Meanwhile, the comprehensive expatriate medical insurance placed by DavidShield has remained largely unaffected by the geopolitical environment.

White Mountains’s noncontrolling equity interest in PassportCard/DavidShield is accounted for at fair value within other long-term investments. As of December 31, 2025 and 2024, White Mountains owned 53.8% basic ownership interest of PassportCard/DavidShield (51.5% on a fully-diluted/fully-converted basis). As of December 31, 2025 and 2024, the fair value of White Mountains’s interest in PassportCard/DavidShield was $170 million and $150 million.

BroadStreet is an insurance brokerage company with a presence in all 50 U.S. states and ten Canadian provinces. BroadStreet focuses on commercial and personal property & casualty insurance and employee benefits. BroadStreet partners with leading insurance agencies, known as core agency partners. Complementing its M&A capabilities and capital solutions, BroadStreet provides a vast network of market resources, tools and expertise to its core agency partners, working alongside them to drive organic growth and improve agency performance.

On July 18, 2025, White Mountains invested $150 million into BroadStreet through the BroadStreet SPV, alongside co-lead investors Ethos Capital LP and British Columbia Investment Management Corporation. See Note 2 — “Significant Transactions” on page F-19. White Mountains’s noncontrolling equity interest in the BroadStreet SPV is accounted for at fair value using NAV as a practical expedient and is included within other long-term investments. As of December 31, 2025, the fair value of White Mountains’s interest in the BroadStreet SPV was $160 million. As of December 31, 2025, White Mountains had a 10.9% limited partnership interest in the BroadStreet SPV and a less than 5% ownership of BroadStreet on a look-through basis.

Elementum

Elementum is a third-party registered investment adviser specializing in natural catastrophe insurance-linked securities (“ILS”). Elementum manages separate accounts and pooled investment vehicles across various ILS sectors, including catastrophe bonds, collateralized reinsurance investments and industry loss warranties on behalf of third-party clients.

White Mountains has a noncontrolling equity interest in Elementum, which is accounted for at fair value within other long-term investments. As of December 31, 2025 and 2024, the fair value of White Mountains’s interest in Elementum totaled $35 million. As of December 31, 2025 and 2024, White Mountains had a 26.6% limited partnership interest in Elementum (25.4% on a fully-diluted/fully-converted basis).

White Mountains also has investments in ILS funds managed by Elementum. As of December 31, 2025 and 2024, White Mountains had $50 million and $74 million invested in ILS funds managed by Elementum.

WTM Partners

In October 2023, White Mountains announced the launch of WTM Partners, which will acquire businesses in non-insurance, non-financial services sectors including essential services, light industrial and specialty consumer. White Mountains expects to deploy up to $500 million of equity capital through WTM Partners over time. WTM Partners deployed $58 million in Enterprise Solutions in 2025, which was the first acquisition by WTM Partners. WTM Partners did not deploy any equity capital in 2024.

Enterprise Solutions

On April 1, 2025, White Mountains acquired a controlling financial interest in Enterprise Solutions (the “Enterprise Solutions Transaction”). See Note 2 — “Significant Transactions” on page F-19. Enterprise Solutions provides specialty electrical contracting services to commercial and institutional customers. As of December 31, 2025, White Mountains reported $178 million of total assets and $90 million of total equity related to Enterprise Solutions. As of December 31, 2025, White Mountains owned 65.5% of Enterprise Solutions on a basic units outstanding basis (59.0% on a fully-diluted/fully-converted basis, taking account of management’s equity incentives) and reported $31 million of noncontrolling interests.

Bamboo CRVs

The Bamboo CRVs are special purpose collateralized reinsurance vehicles that provide reinsurance capacity to Bamboo. White Mountains capitalized the Bamboo CRVs by purchasing preference shares that were deposited into collateral trust accounts. The Bamboo CRVs entered into collateralized quota share agreements with certain of Bamboo’s fronting partners to provide reinsurance protection on Bamboo’s admitted and non-admitted business written in the 2025 and 2024 treaty years. As of December 31, 2025, White Mountains’s total commitment to the Bamboo CRVs was $10 million.

Other Operating Businesses

White Mountains has controlling equity interests in various other operating businesses which are consolidated. As of December 31, 2025, White Mountains reported $87 million of total assets, $54 million of total equity (net of intercompany eliminations) and $6 million of noncontrolling interests related to these businesses. As of December 31, 2024, White Mountains reported $100 million of total assets, $65 million of total equity (net of intercompany eliminations) and $9 million of noncontrolling interests related to these businesses.

White Mountains also has noncontrolling equity interests in various other operating businesses, which are generally accounted for at fair value within other long-term investments. As of December 31, 2025 and 2024, the fair value of these interests totaled $58 million and $49 million.