Mr. John Varnell reports

INTENTION TO MAKE A NORMAL COURSE ISSUER BID FOR SUBORDINATE VOTING SHARES AND PREFERRED SHARES

The Toronto Stock Exchange has accepted a notice filed by Fairfax Financial Holdings Ltd. of its intention to commence a normal course issuer bid (NCIB) through the facilities of the TSX (or other alternative Canadian trading systems) for its subordinate voting shares and the following series of its preferred shares: cumulative five-year rate reset preferred shares, Series C, cumulative floating rate preferred shares, Series D, cumulative five-year rate reset preferred shares, Series E, cumulative floating rate preferred shares, Series F, cumulative five-year rate reset preferred shares, Series G, cumulative floating rate preferred shares, Series H, cumulative five-year rate reset preferred shares, Series I, cumulative floating rate preferred shares, Series J, cumulative five-year rate reset preferred shares, Series K, and cumulative five-year rate reset preferred shares, Series M. Purchases will be made in accordance with the rules and policies of the TSX. Subordinate voting shares purchased will be either cancelled or reserved for share-based payment awards and preferred shares purchased will be cancelled.

As stated in the notice, Fairfax's board of directors has approved the purchase on the TSX, during the period commencing Sept. 30, 2023, and ending Sept. 29, 2024, of subordinate voting shares and preferred shares up to the limits noted herein.

Fairfax is making this NCIB because it believes that in appropriate circumstances its subordinate voting shares and preferred shares represent an attractive investment opportunity and that, with respect to the subordinate voting shares, purchases under the bid will enhance the value of the subordinate voting shares held by the remaining shareholders.

Pursuant to its existing normal course issuer bid, Fairfax sought and received approval from the TSX to purchase up to 2,381,484 subordinate voting shares, 751,034 Series C shares, 178,415 Series D shares, 543,613 Series E shares, 179,629 Series F shares, 771,984 Series G shares, 228,015 series H shares, 1,042,010 Series I shares, 157,989 Series J shares, 950,000 Series K shares and 919,600 Series M shares. Under its existing normal course issuer bid, Fairfax has purchased 436,414 of its subordinate voting shares, which included subordinate voting shares reserved for share-based payment awards, through open market purchases on the TSX during the last 12 months at a volume-weighted average price per share of $891.97. Fairfax has not purchased any preferred shares under its existing normal course issuer bid.

Fairfax also announces that it has entered into an automatic share purchase plan (ASPP) with a designated broker to allow for the purchase of its subordinate voting shares and each series of its preferred shares under the NCIB at times when Fairfax normally would not be active in the market due to applicable regulatory restrictions or internal trading blackout periods. Before the commencement of any particular internal trading blackout period, Fairfax may, but is not required to, instruct its designated broker to make purchases of subordinate voting shares and/or preferred shares under the NCIB during the ensuing blackout period in accordance with the terms of the ASPP. Such purchases will be determined by the broker in its sole discretion based on parameters established by Fairfax prior to commencement of the applicable blackout period in accordance with the terms of the ASPP and applicable TSX rules. Outside of these blackout periods, subordinate voting shares and preferred shares will be purchasable by Fairfax at its discretion under its NCIB.

The ASPP is effective as of Sept. 30, 2023, and will terminate on the earliest of the date on which: (a) the maximum annual purchase limit in respect of the subordinate voting shares and each series of preferred shares under the NCIB has been reached; (b) the NCIB expires; or (c) Fairfax terminates the ASPP in accordance with its terms. The ASPP constitutes an automatic securities purchase plan under applicable Canadian securities laws.

About Fairfax Financial Holdings Ltd.

Fairfax is a holding company which, through its subsidiaries, is primarily engaged in property and casualty insurance and reinsurance and the associated investment management.