Exhibit 10.10

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. The Program is
overseen by the Compensation Committee of the Board of Directors of White
Mountains (the “Compensation Committee”). At the end of each year, separate
bonus pools are established for the non-investment personnel and the investment
personnel based on performance. In general, the bonus pool may range from 0% to
200% of the target.

ANNUAL BONUS POOL DETERMINATION

For non-investment personnel, the size of the annual bonus pool at target is the
sum of the individual target bonuses for participants in the program. For senior
executives, the individual target typically is 75% of salary; more junior
personnel receive progressively lower targets. The annual bonus pool can range
from 0% to 200% of target. The bonus pool payout percentage is determined by the
Compensation Committee using its judgment.

For investment personnel, the size of the annual bonus pool at target is
established in the same manner as for non-investment personnel. The most senior
investment executives typically have an individual target of 125% of salary;
more junior investment personnel receive progressively lower targets. The annual
bonus pool can range from 0% to 200% of target. The bonus pool payout percentage
is determined by the Compensation Committee using its judgment. In determining
the bonus pool payout percentage for investment personnel, the Compensation
Committee considers the following factors, among others: absolute level of
investment results, investment performance as compared to a range of relevant
benchmarks, peer company investment results, and corporate circumstances and
their effect on pure investment performance.

INDIVIDUAL AWARDS

Individual bonuses can vary widely around the pool average based on individual
performance and no cap (other than the size of the pool) applies to any single
individual.

A limited number of special bonuses may be awarded in any year to recognize
successful individual results without regard to the aggregate size of an annual
bonus pool.

PROGRAM PARTICIPATION FOR NEW HIRES

Annual bonuses of those eligible employees hired during the year are typically
pro-rated based on date of hire.

CLAWBACK POLICY
In 2010, White Mountains adopted a clawback policy applicable to bonuses. If
White Mountains is required to restate any financial statement included in an
SEC filing as a result of an employee’s misconduct, the Board may, without
prejudice to any other remedies available, seek reimbursement of any bonus
received by such person that relates in whole or in part to any period for which
such financial statements were restated. If the misconduct was fraud, then in
addition to other actions, the Board mandatorily will seek such reimbursement.