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Pineapple Financial Inc.

For the period ended May 27, 2025. Filed May 27, 2025.

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What shareholders are asked to vote on at a company's meeting. It is where to find what directors and top executives are paid, and who owns the most shares.

May 27, 2025 · Filed May 27, 2025

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PAPL$0.98+3.1%Stored close · as of Oct 23, 2026
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DEF 14A 1 formdef14a.htm DEF 14A

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A

PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE

SECURITIES EXCHANGE ACT OF 1934

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

☐Preliminary Proxy Statement
☐Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
☒Definitive Proxy Statement
☐Definitive Additional Materials
☐Soliciting Material Pursuant to Section 240.14a-12

PINEAPPLE FINANCIAL INC.

(Name of Registrant as Specified in Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

☒No fee required.
☐Fee paid previously with preliminary materials.
☐Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1

May 27, 2025

Notice of SPECIAl Meeting of Stockholders

To the Stockholders of Pineapple Financial Inc.:

We hereby notify you that a special meeting of stockholders (the “Special Meeting”) of Pineapple Financial Inc., a Canadian corporation (the “Company”), will be held on June 26, 2025 beginning at 9:30a.m. Eastern Time, at the Company’s offices, Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1 for the following purposes:

(1)to approve by special resolution, at the discretion of our Board of Directors (the “Board of Directors”), to effect a reverse stock split (i.e. consolidation) with respect to the Company’s issued and outstanding common shares, no par value (“Common Shares”), at a ratio of between 1-for-10 to 1-for-20 (the “Range” ), with the ratio within such Range to be determined at the discretion of the Board and included in a public announcement, subject to the authority of the Board of Directors to abandon the reverse stock split (the “Reverse Stock Split Proposal”);
(2)to approve by ordinary resolution, for purposes of complying with the NYSE American LLC (the “NYSE American”) listing rules, of the issuance of 20% or more of the Company’s issued and outstanding Common Shares as of November 13, 2024, pursuant to a securities purchase agreement (the “Purchase Agreement”) with the purchasers named therein (the “Investors”), dated November 13, 2024, upon the exercise of warrants issuable pursuant to the Purchase Agreement (the “Share Issuance Proposal”); and
(3)to approve by ordinary resolution an adjournment of the Special Meeting to a later date or dates, if necessary, to permit further solicitation and vote of proxies in the event there are not sufficient votes in favor of the Reverse Stock Split Proposal or the Share Issuance Proposal.

The matters listed in this notice of meeting are described in detail in the accompanying proxy statement. Our Board of Directors has fixed the close of business on May 23, 2025 (the “Record Date”) as the record date for determining those stockholders 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 stockholders of record as of the close of business on the Record Date will be made available for inspection at the meeting and will be available for the ten days preceding the 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 STOCKHOLDERS TO BE HELD ON JUNE 26, 2025

On or about May 27, 2025, we will begin mailing the proxy statement. This Notice of Special Meeting of Stockholders 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 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.

By order of the Board of Directors,

/s/ Shubha Dasgupta

Shubha Dasgupta

Chief Executive Officer

Table of Contents

Page
PROXY STATEMENT1
QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING2
PROPOSAL 1: REVERSE STOCK SPLIT PROPOSAL8
PROPOSAL 2: SHARE ISSUANCE PROPOSAL19
PROPOSAL 3: ADJOURNMENT PROPOSAL22
SECURITY OWNERSHIP OF MANAGEMENT AND CERTAIN BENEFICIAL OWNERS23
NOTICE REGARDING DELIVERY OF STOCKHOLDER DOCUMENTS (“HOUSEHOLDING” INFORMATION)24
STOCKHOLDER PROPOSALS FOR THE 2025 ANNUAL MEETING25

i

Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1

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The text of this filing, as the company filed it with the SEC, without its images or exhibits. This is not investment advice.