Pineapple Financial Inc.

DEF 14A 1 formdef14a.htm DEF 14A

**UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, DC 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(c) of the Securities Exchange Act of 1934

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

PINEAPPLE FINANCIAL INC.

(Name of Registrant as Specified in its Charter)

Payment of Filing Fee (Check the appropriate box):

☒ No fee required.

☐ Fee paid previously with preliminary materials.

☐ Fee computed on table in exhibit required by Item 25(b) of Schedule (17 CFR 240.14a-101) per Item 1 of this Schedule and Exchange Act Rules 14c-5(g) and 0-11

**PINEAPPLE FINANCIAL INC.

Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1

NOTICE OF SPECIAL MEETING OF SHAREHOLDERS

To Be Held at 9:30 a.m. Eastern Time on October 31, 2025

To the Shareholders of Pineapple Financial Inc.

We hereby notify you that a special meeting (the “Special Meeting”) of the holders of common shares without par value (“Shareholders”) of Pineapple Financial Inc., a corporation continued and existing under theCanada Business Corporations Act (the “Company”), will be held on October 31, 2025, at 9:30 a.m. Eastern Time, at the Company’s offices at Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1 for the following purposes:

(1) to consider and, if deemed advisable, to approve, with or without variation, pursuant to Rules 712 and 713 of the NYSE American LLC ( “NYSE American”) Company Guide, as applicable an ordinary resolution approving the issuance of 24,642,700 common shares without par value in the capital of the Company (the “SR Common Shares”) issuable in exchange for 24,642,700 subscription receipts (the “Subscription Receipts”) issued and sold pursuant to that certain securities purchase agreement, dated September 2, 2025 (the “Securities Purchase Agreement”) between the Company and the purchasers identified on the signature pages thereto (the “Share Issuance Proposal” or “Proposal 1”), as more particularly described in the accompanying proxy statement (the “Proxy Statement”); and

(2) to consider and, if deemed advisable, to approve, with or without variation, a special resolution approving an amendment to the Company’s Articles of Continuance (the “Articles of Continuance”) to remove the restriction on transfers of common shares without par value in the capital of the Company (“Common Shares”) contained therein (the “Restriction Removal Proposal” or “Proposal 2”), as more particularly described in the Proxy Statement;

(3) to transact such other business as may properly be brought before the Special Meeting or any adjournment thereof.

The matters listed in this notice of meeting (this “Notice of Special Meeting”) are described in detail in the Proxy Statement. The Board of Directors of the Company (the “Board”) has fixed the close of business on September 15, 2025 (the “Record Date”), as the record date for determining those Shareholders who are entitled to notice of and to vote at the Special Meeting or any adjournment or postponement of the Special Meeting. The list of the Registered Shareholders (as defined in the Proxy Statement) as of the close of business on the Record Date will be made available for inspection at the Special Meeting and will be available for the ten days preceding the Special Meeting at the Company’s offices located at Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3RI, during ordinary business hours for any purpose germane to the Special Meeting.

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE Special MEETING OF SHAREHOLDERS TO BE HELD ON OCTOBER 31, 2025

On or about September 30, 2025, we will commence mailing the Proxy Statement and related meeting materials. This Notice of Special Meeting and the Proxy Statement are available atgopineapple.com.

YOUR VOTE IS IMPORTANT. WHETHER OR NOT YOU PLAN TO ATTEND THE Special MEETING IN PERSON, PLEASE SUBMIT A PROXY TO HAVE YOUR COMMON SHARES VOTED AS PROMPTLY AS POSSIBLE BY USING THE INTERNET OR BY SIGNING, DATING AND RETURNING BY MAIL THE PROXY CARD ENCLOSED WITH THE PROXY MATERIALS. IF YOU DO NOT RECEIVE THE PROXY MATERIALS IN PRINTED FORM AND WOULD LIKE TO SUBMIT A PROXY BY MAIL, YOU MAY REQUEST A PRINTED COPY OF THE PROXY MATERIALS AND SUCH MATERIALS WILL BE SENT TO YOU.

If you are a Shareholder and wish to dissent in respect of the Restriction Removal Proposal, you must strictly comply with the dissent procedures set out in Section 190 of theCanada Business Corporations Act(the “CBCA”). As a result of delivering a valid notice of dissent in connection with the Restriction Removal Proposal, if the Restriction Removal Proposal becomes effective, you will be entitled to be paid the fair value of your Common Shares, subject to strict compliance with Section 190 of the CBCA in respect of the Restriction Removal Proposal. The rights to dissent are described in the section of the Proxy Statement entitled “Proposal 2 – Restriction Removal Proposal – Dissent Rights” and the text of the section 190 of the CBCA is set forth in Appendix “A” to the Proxy Statement. Failure to strictly comply with such requirements may result in the loss or unavailability of any right of dissent.

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Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1