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Esurance Celebrates 10 Years of Innovation

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San Francisco, CA — December 16, 2009

Esurance, the direct-to-consumer personal auto insurance company, celebrates its tenth anniversary today — an important milestone for the innovative company. Since Esurance launched on December 16, 1999, it has been dedicated to improving the way people shop for, buy, and manage their auto insurance. Over the past 10 years, Esurance has sold more than 1.5 million auto insurance policies, and insured more than 2.2 million drivers.

Over the past decade, Esurance has become the third-most recognized personal auto insurance provider on the Internet. By combining best-in-class Web-enabled technology, underwriting expertise, and a culture of continuous improvement, Esurance has become a leader in a competitive industry.

President and Chief Executive Officer Gary Tolman reflected on the last 10 years by saying, "Our parent company, White Mountains Insurance Group, Ltd. (NYSE: WTM), helped nurture Esurance as we became a significant competitor in the personal auto insurance space. We are grateful for their tremendous support over the years. Now, after a decade in business, Esurance has matured into an established, well-known insurance carrier."

Esurance began offering Web-enabled insurance services years before most of its more established competitors. With real-time underwriting verification, electronic signatures, and actionable comparison quotes, Esurance was one of the leaders in making the purchase of auto insurance simpler and faster for customers. In the past 10 years, Esurance has built reliable, proprietary, Web-based systems throughout its entire technology infrastructure, including quoting and purchasing, policy management, billing, customer service, and claims handling.

In 2004, Esurance launched television advertising featuring the company's animated icon, Erin Esurance. The colorful animated television spots helped Esurance stand out in a competitive category and supported the Esurance brand as innovative and fun — adjectives not often used to describe personal auto insurance. Today, the Esurance brand is recognized by 2 out of 3 people in the United States.

More recently, White Mountains' purchase of Answer Financial, one of the largest U.S. personal insurance agencies, brought it and its capabilities into the Esurance family. Esurance has partnered with Answer Financial since 2003, but the enhanced relationship now allows consumers shopping on the Esurance website to purchase insurance coverage from multiple leading insurance companies.

Esurance has earned an "A-" (Excellent) rating from A.M. Best Company, an independent firm that rates the financial strength and performance of insurance companies.

Tolman concluded, "We will use our experience from the last 10 years to guide our success in the next decade. I am proud of what we have accomplished, and I would like to thank all of our associates for their continuing hard work and dedication to the company. We very much look forward to the next 10 years."

About Esurance®

Esurance, a subsidiary of White Mountains Insurance Group, Ltd. (NYSE: WTM), provides personal auto insurance direct to consumers online and through select online agents. Through hassle-free coverage, 24/7 customer service, and competitive prices, Esurance is dedicated to constantly improving the way people shop for, buy, and manage their auto insurance. By combining the best of technology with industry know-how, Esurance is able to offer hassle-free coverage with 24/7 customer service and claims handling at competitive prices.

Through Esurance's website, www.esurance.com, customers can get instant quotes, view comparison quotes, buy an Esurance policy, and print their insurance cards in just minutes. Esurance also offers policyholders the ability to make policy changes and file claims instantly online, demonstrating its commitment to improving the entire insurance process from quote to claim.