Pineapple Financial Inc.

For the Special Meeting of Shareholders to be held on October 31, 2025

General Information

Information in this proxy statement is provided as of September 29, 2025, unless otherwise noted.

We are providing these proxy materials, including the attached notice of meeting (the “Notice of Special Meeting”), form of proxy (the “Form of Proxy”) and voting instruction form (“VIF”) to holders (“Shareholders”) of common shares without par value (the “Common Shares”) in the capital of Pineapple Financial Inc., a corporation continued and existing under theCanada Business Corporations Act (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 Shareholders (the “Special Meeting”) to be held on October 31, 2025, beginning at 9:30 a.m. Eastern Time at Pineapple’s 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 (this “Proxy Statement”) is being distributed and made available to our Shareholders starting on or about September 29, 2025. The purpose of the Special Meeting and the matters to be acted on are summarized below.

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.

MEETING LOCATION and FORMAT

The Special Meeting will be held at Pineapple’s offices, located at Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1. Pineapple strongly encourages all Shareholders to vote their Common Shares in advance of the Special Meeting using the Form of Proxy or VIF, as applicable. The Board and management of the Company will address the Special Meeting and Shareholders will be able to ask questions at the Special Meeting. Voting in advance of the Special Meeting using the Form of Proxy for Registered Shareholders (as defined herein) and VIF for Non-Registered Shareholders (as defined herein) in accordance with the instructions set out on your Form of Proxy or VIF, as applicable, will ensure your votes are counted at the Special Meeting.

We encourage you to make sure that your votes are represented at the Special Meeting. Please take the time to vote using the Form of Proxy or VIF, as applicable, sent to you in accordance with the instructions thereon so that your Common Shares are voted according to your instructions and represented at the Special Meeting.

In accordance with the provisions of theCanada Business Corporations Act (the “CBCA”), the Board of Directors has fixed September 15, 2025 (the “Record Date”), as the record date for the purpose of determining Shareholders entitled to vote at the Special Meeting. The Company will prepare a list of holders of its Common Shares as at the close of business on the Record Date. A Shareholder named in the list will be entitled to vote the Common Shares shown opposite their name at the Special Meeting and all adjournments thereof.

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

SOLICITATION OF PROXIES

This Proxy Statement is furnished in connection with the solicitation by and on behalf of the management of the Company of proxies to be used at the Special Meeting for the purposes set forth in the Notice of Special Meeting. It is expected that the solicitation will be primarily by mail or email. Employees of the Company may solicit proxies personally or by telephone at nominal cost. The cost of any such solicitation by management will be borne by the Company.

MANNER OF VOTING AND EXERCISE OF DISCRETION BY PROXIES

The persons named in the Form of Proxy will vote the Common Shares in respect of which they are appointed in accordance with the direction of the Shareholders appointing them. In the absence of such direction, such Common Shares will be votedFOR Proposal 1 (as defined herein) andFOR Proposal 2 (as defined herein).

The Form of Proxy confers discretionary authority upon the persons named therein with respect to any amendments or variations to matters identified in the Notice of Special Meeting and with respect to other matters which may properly come before the Special Meeting or any adjournment thereof. As of the date of this Proxy Statement, management of the Company knows of no such amendments, variations or other matters to come before the Special Meeting other than the matters referred to in the Notice of Special Meeting.

APPOINTMENT OF PROXIES

The persons named in the enclosed Form of Proxy are officers of the Company.A Shareholder desiring to appoint some other person to represent them at the Special Meeting may do so by inserting such person’s name, who need not be a Shareholder, in the blank space provided in the Form of Proxy and striking out the names of the two persons specifiedin the Form of Proxy,or by completing another proper form of proxy.

In all cases, the completed proxy is to be delivered to Endeavor Trust Corporation at 702 –777 Hornby Street, Vancouver, BC V6Z 1S4 on October 29, 2025.

REVOCATION OF PROXIES

A Shareholder of record of the Company (a “Registered Shareholder”) who has given a proxy may revoke the proxy as to any motion on which a vote has not already been cast pursuant to the authority conferred by it by: (a) depositing an instrument in writing, including another completed form of proxy, executed by such Registered Shareholder or by his or her attorney authorized in writing or by electronic signature or, if the Registered Shareholder is a corporation, by an officer or attorney thereof properly authorized, with Endeavor Trust Corporation at 702 –777 Hornby Street, Vancouver, BC V6Z 1S4, on October 29, 2025; or (ii) with the chair of the Special Meeting on the day of the Special Meeting or any adjournment thereof; (b) transmitting, by telephone or electronic means, a revocation that complies with paragraph (i) or (ii) above and that is signed by electronic signature, provided that the means of electronic signature permits a reliable determination that the document was created or communicated by or on behalf of such Shareholder or by or on behalf of his or her attorney, as the case may be; or (c) in any other manner permitted by law including attending the Special Meeting in person.

VOTING BY NON-REGISTERED SHAREHOLDERS

The information set forth in this section is of significant importance to many Shareholders of the Company as a substantial number of Shareholders do not hold their Common Shares in their own name and thus are considered beneficial shareholders (“Non-Registered Shareholders”). If Common Shares are listed in an account statement provided to a Shareholder by a broker then, in almost all cases, those Common Shares will not be registered in the Shareholder’s name on the records of the Company. Such Common Shares will more likely be registered under the name of the Shareholder’s broker or an agent of that broker or another similar intermediary holding on the Shareholder’s behalf.

If you have received the Company’s Form of Proxy directly, you may vote your shares on the Internet in accordance with the instructions on the Form of Proxy, or you may also return it to Endeavor Trust Corporation by regular mail in the return envelope provided.

Only Registered Shareholders, or the persons they appoint as their proxies, are entitled to attend and vote at the Special Meeting. Non-Registered Shareholders will receive a VIF from an intermediary by way of instruction of their financial institution. Detailed instructions of how to submit your vote (including voting on the Internet) will be on the VIF. Non-Registered Shareholders should return their voting instructions as specified in the request for voting instructions.

In either case, the purpose of this procedure is to permit Non-Registered Shareholders to direct the voting of the Common Shares they beneficially own. Should a Non-Registered Shareholder who receives either a Form of Proxy or VIF wish to vote at the Special Meeting in person, the Non-Registered Shareholder should strike out the persons named in the Form of Proxy or VIF and insert the Non-Registered Shareholder’s name in the blank space provided or, in the case of a VIF, follow the directions indicated on the VIF. Non-Registered Shareholders who receive a VIF from an intermediary should carefully follow the instructions of their intermediary, including those regarding when and where the VIF is to be delivered.

A Non-Registered Shareholder who has submitted a VIF may revoke it by contacting the intermediary through which the Non-Registered Shareholder’s Common Shares are held and following the intermediary’s instructions. A Non-Registered Shareholder who has submitted the Company’s Form of Proxy may revoke it in the manner described in the Form of Proxy. Please refer to the sections entitled “Appointment of Proxies” and “Revocation of Proxies”.

These proxy materials are being sent directly to Registered Shareholders and indirectly to Non-Registered Shareholders.

VOTING SHARES AND RECORD DATE

The Company is authorized to issue an unlimited number of Common Shares with each share carrying the right to one vote per share at all meetings of the Shareholders.

As of September 15, 2025, the Company had 1,345,941 Common Shares issued and outstanding.

In accordance with the provisions of the CBCA, the Board of Directors has fixed September 15, 2025, as the Record Date for the purpose of determining Shareholders entitled to vote at the Special Meeting. The Company will prepare a list of holders of its Common Shares as at the close of business on the Record Date. A Shareholder named in the list will be entitled to vote the Common Shares shown opposite their name at the Special Meeting and any adjournment thereof.

QUORUM

The presence, either in person, by proxy or by authorized representative, of two holders of our Common Shares outstanding and entitled to vote on the Record Date are necessary to constitute a quorum. Abstentions are treated as present for purposes of determining whether a quorum exists. Your shares will be counted towards the quorum only if you submit a valid proxy (or, in the case of a beneficial owner, one is submitted on your behalf by your broker, bank or other nominee) or if you attend the Special Meeting in person. Broker non-votes (which result when your shares are held in “street name”, and you do not tell the nominee how to vote your shares and the nominee does not have discretion to vote such shares) are treated as present for purposes of determining whether a quorum is present at the meeting.

PARTICULARS OF MATTERS TO BE ACTED UPON AT THE MEETING

Unless otherwise noted, approval of matters to be placed before the Special Meeting will be by way of an “ordinary resolution”, which is a resolution passed by a simple majority (50% plus 1) of the votes cast by Shareholders entitled to vote and present in person or represented by proxy.

A “special resolution” placed before the Special Meeting is a resolution passedby at least two-thirds (66⅔%) of the votes cast by Shareholdersentitled to vote and present in person or by proxy.