Pineapple Financial Inc.

For the Special Meeting of Stockholders to be held on june 26, 2025

General Information

We are providing these proxy materials to holders of common shares, no par value per share (“Common Shares”), of Pineapple Financial Inc., a Canadian corporation (referred to as “Pineapple,” the “Company,” “we,” or “us”), in connection with the solicitation by the Board of Directors of Pineapple (the “Board of Directors” or the “Board”) of proxies to be voted at our special meeting of stockholders (the “Special Meeting”) to be held on June 26, 2025, beginning at 9:30 a.m. Eastern Time at Pineapples’ offices located at Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1, and at any adjournment or postponement of the Special Meeting. This proxy statement is being distributed and made available to our stockholders starting on or about May 27, 2025. The purpose of the Special Meeting and the matters to be acted on are summarized below. No other business will come before the Special Meeting.

Even if you plan to attend the Special Meeting, please vote in advance so that your vote will be counted if you later decide not to attend the Special Meeting.

Special Meeting Admission

Only stockholders as of May 23, 2025 (the “Record Date”) may attend the Special Meeting. If you attend, please note that you will be asked to present government-issued identification (such as a driver’s license or passport) and evidence of your share ownership of our Common Shares on the Record Date. Such evidence of ownership can be your proxy card if you are a stockholder of record. If your shares are held beneficially in the name of a bank, broker or other holder of record and you plan to attend the Special Meeting, you will be required to present proof of your ownership of our Common Shares on the Record Date, such as a bank or brokerage account statement or voting instruction card, to be admitted to the Special Meeting.

No cameras, recording equipment or electronic devices will be permitted in the Special Meeting.