SEC Form PRE 14A filed by Pineapple Financial Inc.

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:

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):

Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1

May 15, 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:

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 [*], 2025, we will begin mailing the proxy statement. This Notice of Special Meeting of Stockholders and the proxy statement are available at gopineapple.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.

Table of Contents

Unit 200, 111 Gordon Baker Road

Toronto, Ontario M2H 3R1

PROXY STATEMENT

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 [*], 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.

QUESTIONS AND ANSWERS ABOUT THE SPEcial meeting

Other than these proposals, no other proposals will be presented for a vote at the Special Meeting.

Attendance at the meeting will not, by itself, revoke a proxy unless you specifically so request. The last vote received chronologically will supersede any prior votes.

Beneficial Owner: Shares Registered in the Name of Broker or Bank

For shares you hold beneficially, you may change your vote by following the instructions provided by your broker, bank or nominee.

PROPOSAL 1

APPROVAL OF THE REVERSE STOCK SPLIT

The Board of Directors has adopted a resolution proposing to effect a reverse stock split (i.e. consolidation) of the issued and outstanding Common Shares, declared such reverse stock split advisable, and is recommending that our stockholders approve such Reverse Stock Split. Such reverse stock split will be effected after stockholder approval thereof only in the event the Board of Directors still deems it advisable. Holders of the Common Shares are being asked to approve the proposal that the Common Shares be consolidated at a ratio in the range of between one (1) post-consolidation Common Share for every ten (10) pre-consolidation Common Shares and one (1) post-consolidation Common Share for every twenty (20) pre-consolidation Common Shares. If the Reverse Stock Split is approved by our stockholders and if the Board of Directors determines to effect such Reverse Stock Split, the Company will effect the Reverse Stock Split by reducing the outstanding number of Common Shares. If the Board of Directors does not implement an approved Reverse Stock Split prior to the one-year anniversary of the Special Meeting, this vote will be of no further force and effect, and the Board will again seek stockholder approval before implementing any reverse stock split after that time. The Board of Directors may abandon the proposed the Reverse Stock Split at any time prior to its effectiveness, whether before or after stockholder approval thereof.

As of the Record Date, the Company had [*] Common Shares outstanding. For purposes of illustration, if the Reverse Stock Split is effected at a ratio of 1-for-10 the number of issued and outstanding Common Shares after the Reverse Stock Split would be approximately [*] shares. The Board of Directors’ decision as to whether and when to effect the Reverse Stock Split will be based on a number of factors, including market conditions, existing and expected trading prices for the Common Shares, and the continued listing requirements and policies of the NYSE American and the other national securities exchanges. Some of the factors the Board considered in determining the Reverse Stock Split Ratio range, included, but was not limited to, the following: the historical trading price and trading volume of the Common Shares; the expected impact of the Reverse Stock Split on the trading market for the Common Shares in the short-term and long-term, and general market, economic conditions, and other related conditions prevailing in our industry.

The Reverse Stock Split, if effected, will not change the number of authorized shares of Common Shares. As of the date of this proxy statement, our current unlimited authorized Common Shares are sufficient to satisfy all of our share issuance obligations and current financing plans and issuances under our share incentive plans, and we do not have any current plans, arrangements or understandings relating to the issuance of the additional Common Shares that will become available for issuance following the Reverse Stock Split.

Purpose and Background of the Reverse Stock Split

The Board’s primary objective in asking for authority to effect a reverse split is to increase the per-share trading price of our Common Shares and in order to maintain compliance with the requirements and policies of the NYSE American.

The Board further believes that the current low per share market price of our Common Shares has a negative effect on the marketability of our existing shares. The Board believes there are several reasons for this effect. First, certain institutional investors have internal policies preventing the purchase of low-priced stocks. Second, a variety of policies and practices of broker-dealers discourage individual brokers within those firms from dealing in low-priced stocks. Third, because the brokers’ commissions on low-priced stocks generally represent a higher percentage of the stock price than commissions on higher priced stocks, the current price of the Common Shares can result in individual stockholders paying transaction costs (commissions, markups or markdowns) that are a higher percentage of their total share value than would be the case if the price of the Common Shares were substantially higher. This factor is also believed to limit the willingness of some institutions to purchase the Common Shares. The Board anticipates that a Reverse Stock Split will result in a higher bid price for the Common Shares, which may help to alleviate some of these problems.

The Board of Directors believes that the failure of stockholders to approve the Reverse Stock Split Proposal could prevent the market price of our Common Shares from remaining at a level that will be sufficient to meet any requirements and policies of the NYSE American and could inhibit our ability to conduct capital raising activities, among other things. If the NYSE American delists the Common Shares, then the Common Shares would likely become traded on an over-the-counter market such as those maintained by OTC Markets Group Inc., which do not have the substantial corporate governance or quantitative listing requirements for continued trading that the NYSE American has. In that event, interest in Common Shares may decline and certain institutions may not have the ability to trade in the Common Shares, all of which could have a material adverse effect on the liquidity or trading volume of the Common Shares. If the Common Shares become significantly less liquid due to delisting from the NYSE American, our stockholders may not have the ability to liquidate their investments in the Common Shares as and when desired and we believe our ability to maintain analyst coverage, attractive investor interest, and have access to capital may become significantly diminished as a result.

We expect that a Reverse Stock Split of the Common Shares will increase the market price of our Common Shares. However, the effect of a Reverse Stock Split on the market price of the Common Shares cannot be predicted with any certainty, and the history of similar stock split combinations for companies in like circumstances is varied. It is possible that the per share price of the Common Shares after the Reverse Stock Split will not rise in proportion to the reduction in the number of Common Shares outstanding resulting from the Reverse Stock Split, effectively reducing our market capitalization. The market price of our Common Shares may vary based on other factors that are unrelated to the number of shares outstanding, including our future performance.

The Reverse Stock Split will be effected simultaneously for all issued and outstanding Common Shares and the Reverse Stock Split Ratio will be the same for all issued and outstanding Common Shares. The Reverse Stock Split will affect all of our stockholders uniformly and will not affect any stockholder’s percentage ownership interests in our company, except those stockholders who would have otherwise received fractional shares will receive cash in lieu of such fractional shares determined in the manner set forth below under the heading “Fractional Shares.” After the Reverse Stock Split, each of the Common Shares will have the same voting rights and rights to dividends and distributions and will be identical in all other respects to the Common Shares now authorized. The Reverse Stock Split will not affect us continuing to be subject to the periodic reporting requirements of the Exchange Act. The Reverse Stock Split is not intended to be, and will not have the effect of, a “going private transaction” covered by Rule 13e-3 under the Exchange Act.

The Reverse Stock Split may result in some stockholders owning “odd-lots” of less than 100 Common Shares. Brokerage commissions and other costs of transactions in odd-lots are generally higher than the costs of transactions in “round-lots” of even multiples of 100 shares. In addition, we will not issue fractional shares in connection with the Reverse Stock Split, and stockholders who would have otherwise been entitled to receive such fractional shares will receive an amount in cash determined in the manner set forth below under the heading “Fractional Shares.”

Following the effectiveness of the Reverse Stock Split, if approved by the stockholders and implemented by the Company, current stockholders will hold fewer Common Shares.

If the Board decides to implement the Reverse Stock Split, the Company would communicate to the public, prior to the effective time of the Reverse Stock Split, additional details regarding the Reverse Stock Split (including the final Reverse Stock Split Ratio, as determined by the Board). By voting in favor of the Reverse Stock Split, you are also expressly authorizing the Board to determine not to proceed with, and to defer or to abandon, the Reverse Stock Split, in the Board’s sole discretion. In determining whether to implement the Reverse Stock Split following receipt of stockholder approval of the Reverse Stock Split, and which Reverse Stock Split Ratio to implement, if any, the Board may consider, among other things, various factors, such as:

Reasons for the Reverse Stock Split

To increase the per share price of our Common shares

As discussed above, the main objective for effecting the Reverse Stock Split, should our Board choose to effect one, would be to increase the per share price of the Common Shares primarily to maintain compliance with the listing standards and policies of the NYSE American. However, there can be no assurance that the market price of our Common Shares will remain at a level that will be sufficient to meet any requirements and policies of the NYSE American or that our Common Shares will remain listed on the NYSE American. The NYSE American has discretion in determining whether or not to allow a company to stay listed with a low stock price. In the event that we are not successful in maintaining the listing of our Common Shares on the NYSE American, we intend to seek a listing on another national securities exchange, which will also require that the per share trading price of our Common Shares be higher than our current per share trading price. In addition, our Board believes that, should the appropriate circumstances arise, effecting the Reverse Stock Split, could, among other things, help us to appeal to a broader range of investors, generate greater investor interest in the Company, and improve the perception of our Common Shares as an investment security.

To potentially improve the liquidity of the Common Shares

A Reverse Stock Split could allow a broader range of institutions to invest in the Common Shares (namely, funds that are prohibited from buying stocks whose price is below certain thresholds), potentially increasing trading volume and liquidity of the Common Shares and potentially decreasing the volatility of the Common Shares if institutions become long-term holders of the Common Shares. A Reverse Stock Split could help increase analyst and broker interest in the Common Shares as their policies can discourage them from following or recommending companies with low stock prices. Because of the trading volatility often associated with low-priced stocks, many brokerage houses and institutional investors have internal policies and practices that either prohibit them from investing in low-priced stocks or tend to discourage individual brokers from recommending low-priced stocks to their customers. Some of those policies and practices may make the processing of trades in low-priced stocks economically unattractive to brokers. Additionally, because brokers’ commissions on low-priced stocks generally represent a higher percentage of the stock price than commissions on higher-priced stocks, a low average price per Common Shares can result in individual stockholders paying transaction costs representing a higher percentage of their total share value than would be the case if the share price were higher. Some investors, however, may view a Reverse Stock Split negatively since it reduces the number of Common Shares available in the public market.

Potential Anti-takeover Effects of the Reverse Stock Split

Release No. 34-15230 of the staff of the SEC requires disclosure and discussion of the effects of any action, including the proposals discussed herein, that may be used as an anti-takeover mechanism. The relative increase in the number of Common Shares available for issuance vis-à-vis the outstanding Common Shares, could, under certain circumstances, have an anti-takeover effect, although this is not the purpose or intent of the Board. It could potentially deter takeovers, including takeovers that the Board has determined are not in the best interest of our stockholders, in that additional shares could be issued (within the limits imposed by applicable law) in one or more transactions that could make a change in control or takeover more difficult. For example, we could issue additional shares so as to dilute the stock ownership or voting rights of persons seeking to obtain control without our agreement. Similarly, the issuance of additional shares to certain persons allied with our management could have the effect of making it more difficult to remove our current management by diluting the stock ownership or voting rights of persons seeking to cause such removal. By potentially discouraging initiation of any such unsolicited takeover attempts, the Reverse Stock Split may limit the opportunity for our stockholders to dispose of their shares at the higher price generally available in takeover attempts or that may be available under a merger proposal.

Certain Risks Associated with a Reverse Stock Split

Reducing the number of outstanding Common Shares through the Reverse Stock Split Proposal is intended, absent other factors, to increase the per share market price of the Common Shares. Other factors, however, such as our financial results, market conditions, the market perception of our business and other risks, including those set forth in our SEC filings and reports, may adversely affect the market price of the Common Shares. As a result, there can be no assurance that the Reverse Stock Split, if completed, will result in the intended benefits described above, that the market price of the Common Shares will increase following the Reverse Stock Split or that the market price of the Common Shares will not decrease in the future.

The Reverse Stock Split May Not Result in a Sustained Increase in the Price of the Common Shares.

As noted above, the principal purpose of the Reverse Stock Split Proposal is to maintain a higher average per share market closing price of the Common Shares. However, the effect of the Reverse Stock Split upon the market price of the Common Shares cannot be predicted with any certainty and we cannot assure you that the Reverse Stock Split will accomplish this objective for any meaningful period of time, or at all.

The Reverse Stock Split May Decrease the Liquidity of the Common Shares.

The Board believes that the Reverse Stock Split may result in an increase in the market price of the Common Shares, which could lead to increased interest in the Common Shares and possibly promote greater liquidity for our stockholders. However, the Reverse Stock Split will also reduce the total number of outstanding Common Shares, which may lead to reduced trading and a smaller number of market makers for the Common Shares.

The Reverse Stock Split May Result in Some Stockholders Owning “Odd Lots” That May Be More Difficult to Sell or Require Greater Transaction Costs per Share to Sell.

If the Reverse Stock Split is implemented, it will increase the number of stockholders who own “odd lots” of less than 100 Common Shares. A purchase or sale of less than 100 Common Shares (an “odd lot” transaction) may result in incrementally higher trading costs through certain brokers, particularly “full service” brokers. Therefore, those stockholders who own less than 100 Common Shares following the Reverse Stock Split may be required to pay higher transaction costs if they sell their Common Shares.

The Reverse Stock Split May Lead to a Decrease in the Overall Market Capitalization of the Company.

The Reverse Stock Split may be viewed negatively by the market and, consequently, could lead to a decrease in our overall market capitalization. If the per share market price of the Common Shares do not increase in proportion to the Reverse Stock Split Ratio, then our value, as measured by our market capitalization, will be reduced.

Impact of a Reverse Stock Split If Implemented

A Reverse Stock Split would affect all holders of Common Shares uniformly and would not affect any stockholder’s percentage ownership interests or proportionate voting power. The other principal effects of the Reverse Stock Split will be that:

The following table sets forth the approximate number of Common Shares that would be outstanding immediately after the Reverse Stock Split based on the current authorized number of Common Shares at various exchange ratios, based on [*] Common Shares actually outstanding as of the Record Date. The table does not account for fractional shares that will be paid in cash.

Effects of the Reverse Stock Split

Management does not anticipate that our financial condition, the percentage ownership of Common Shares by management, the number of our stockholders or any aspect of our business will materially change as a result of the Reverse Stock Split. Because the Reverse Stock Split will apply to all issued and outstanding Common Shares and outstanding rights to purchase Common Shares or to convert other securities into Common Shares the proposed Reverse Stock Split will not alter the relative rights and preferences of existing stockholders, except to the extent the Reverse Stock Split will result in fractional shares, as discussed in more detail below.

The Common Shares are currently registered under Section 12(b) of the Exchange Act, and we are subject to the periodic reporting and other requirements of the Exchange Act. The Reverse Stock Split will not affect the registration of the Common Shares under the Exchange Act or the listing of the Common Shares on the NYSE American (other than to the extent it facilitates compliance with the NYSE American requirements and policies). Following the Reverse Stock Split, the Common Shares will continue to be listed on the NYSE American, although we will receive a new Committee on Uniform Securities Identification Procedures, or CUSIP, number.

The rights of the holders of the Common Shares will not be affected by the Reverse Stock Split, other than as a result of the treatment of fractional shares as described below. For example, a holder of 2% of the voting power of the outstanding shares of the Common Shares immediately prior to the effectiveness of the Reverse Stock Split will generally continue to hold 2% of the voting power of the outstanding Common Shares immediately after effecting the Reverse Stock Split. The number of stockholders of record will not be affected by the Reverse Stock Split (except to the extent any are cashed out as a result of holding fractional shares). If approved and implemented, the Reverse Stock Split may result in some stockholders owning “odd lots” of less than 100 Common Shares. Odd lot shares may be more difficult to sell, and brokerage commissions and other costs of transactions in odd lots are generally higher than the costs of transactions in “round lots” of even multiples of 100 shares. The Board believes, however, that these potential effects are outweighed by the benefits of the Reverse Stock Split.

Effectiveness of the Reverse Stock Split

The Reverse Stock Split, if approved by our stockholders, would become effective upon the time so determined by the Board of Directors to effect such Reverse Stock Split (the “Effective Time”). The exact timing of the Reverse Stock Split would be determined by the Board based on its evaluation as to when such action would be the most advantageous to us and our stockholders. In addition, the Board reserves the right, notwithstanding stockholder approval and without further action by the stockholders, to elect not to proceed with the Reverse Stock Split at any time prior to effect of the Reverse Stock Split if the Board of Directors, in its sole discretion, determines that it is no longer in our best interests or the best interests of our stockholders to proceed with the Reverse Stock Split. If our Board of Directors does not implement the Reverse Stock Split prior to the one-year anniversary of the date on which the Reverse Stock Split is approved by our stockholders at the Special Meeting, the authority granted in this proposal to implement the Reverse Stock Split will terminate and the Reverse Stock Split will be abandoned.

Effect on Par Value; Reduction in Stated Capital

The proposed Reverse Stock Split will not affect the par value of our stock, which will remain at no par value.

Book-Entry Shares

If the Reverse Stock Split is effected, stockholders, either as direct or beneficial owners, will have their holdings electronically adjusted by our transfer agent (and, for beneficial owners, by their brokers or banks that hold in “street name” for their benefit, as the case may be) to give effect to the Reverse Stock Split. Banks, brokers, custodians or other nominees will be instructed to effect the Reverse Stock Split for their beneficial holders holding Common Shares in street name. However, these banks, brokers, custodians or other nominees may have different procedures than registered stockholders for processing the Reverse Stock Split and making payment for fractional shares. If a stockholder holds Common Shares with a bank, broker, custodian or other nominee and has any questions in this regard, stockholders are encouraged to contact their bank, broker, custodian or other nominee. We do not issue physical certificates to stockholders.

No Appraisal Rights

Under Canadian Law, our stockholders are not entitled to dissenters’ rights or appraisal rights with respect to the Reverse Stock Split described in the Reverse Stock Split Proposal, and we will not independently provide our stockholders with any such rights.

Fractional Shares

We do not intend to issue fractional shares in connection with the Reverse Stock Split. and, in lieu thereof, any person who would otherwise be entitled to a fractional Common Share as a result of the reclassification and combination following the Effective Time (after taking into account all fractional Common Shares otherwise issuable to such holder) shall be entitled to receive a cash payment equal to the number of Common Shares held by such stockholder before the Reverse Stock Split that would otherwise have been exchanged for such fractional share interest multiplied by the average closing sales price of the Common Shares as reported on the NYSE American for the ten days preceding the Effective Time. After the Reverse Stock Split is effected, a stockholder will have no further interest in our Company with respect to its fractional share interest and persons otherwise entitled to a fractional share will not have any voting, dividend or other rights with respect thereto, except to receive the above-described cash payment. Stockholders should be aware that under the escheat laws of various jurisdictions, sums due for fractional interests that are not timely claimed after the Effective Time may be required to be paid to the designated agent for each such jurisdiction. Stockholders otherwise entitled to receive such funds, who have not received them, will have to seek to obtain such funds directly from the jurisdiction to which they were paid.

Material U.S. Federal Income Tax Considerations Related to the Reverse Stock Split

The following is a general summary of the material U.S. federal income tax considerations to U.S. holders (as defined below) of the Reverse Stock Split. This discussion is based upon current provisions of the Internal Revenue Code of 1986, as amended (the “Code”), existing and proposed Treasury regulations promulgated under the Code (the “Treasury Regulations”) and judicial authority and administrative interpretations, all as of the date of this document, and all of which are subject to change, possibly with retroactive effect, and are subject to differing interpretations. Changes in these authorities may cause the tax consequences to vary substantially from the consequences described below. We have not sought and will not seek an opinion of counsel or any rulings from the Internal Revenue Service (the “IRS”) with respect to any of the tax considerations discussed below. As a result, there can be no assurance that the IRS will not assert, or that a court would not sustain, a position contrary to any of the conclusions set forth below.

This discussion is limited to U.S. holders (except to the extent such discussion explicitly addresses non-U.S. holders) that hold Common Shares as “capital assets” within the meaning of Section 1221 of the Code (generally, property held for investment). This discussion does not address any tax consequences arising under the tax on net investment income or the alternative minimum tax, nor does it address any tax consequences arising under the laws of any state, local or non-U.S. jurisdiction, U.S. federal estate or gift tax laws, or any tax treaties. Furthermore, this discussion does not address all aspects of U.S. federal income taxation that may be applicable to U.S. holders in light of their particular circumstances or to U.S. holders that may be subject to special rules under U.S. federal income tax laws, including, without limitation:

If a partnership, or any entity (or arrangement) treated as a partnership for U.S. federal income tax purposes, holds Common Shares, the tax treatment of a partner in such partnership generally will depend on the status of the partner and the activities of the partnership and upon certain determinations made at the partner level. Partnerships holding Common Shares and partners in such partnerships should consult their own tax advisors about the U.S. federal income tax consequences of the Reverse Stock Split.

For purposes of this discussion, a “U.S. holder” is a beneficial owner of shares of Common Shares that is for U.S. federal income tax purposes:

A “non-U.S. holder” is, for U.S. federal income tax purposes, a beneficial owner of shares of Common Shares that is a not a U.S. holder or a partnership for U.S. federal income tax purposes.

Tax Consequences of the Reverse Stock Split Generally

The Reverse Stock Split should constitute a “recapitalization” for U.S. federal income tax purposes. As a result, a U.S. holder of Common Shares generally should not recognize gain or loss upon the Reverse Stock Split, except with respect to cash received in lieu of a fractional Common Share, as discussed below. A U.S. holder’s aggregate tax basis in the Common Shares received pursuant to the Reverse Stock Split should equal the aggregate tax basis of the Common Shares surrendered (excluding any portion of such basis that is allocated to any fractional share of Common Shares), and such U.S. holder’s holding period in the Common Shares received should include the holding period in the Common Shares surrendered. Treasury Regulations provide detailed rules for allocating the tax basis and holding period of the Common Shares surrendered to the Common Shares received in a recapitalization pursuant to the Reverse Stock Split. U.S. holders of Common Shares acquired on different dates and at different prices should consult their tax advisors regarding the allocation of the tax basis and holding period of such shares.

Cash in Lieu of Fractional Shares

A U.S. holder of Common Stock that receives cash in lieu of a fractional share of Common Stock pursuant to the Reverse Stock Split and whose proportionate interest in us is reduced (after taking into account certain constructive ownership rules) should generally recognize capital gain or loss in an amount equal to the difference between the amount of cash received and the U.S. holder’s tax basis in the Common Shares surrendered that is allocated to such fractional Common Share. Such capital gain or loss should be long-term capital gain or loss if the U.S. holder’s holding period for Common Shares surrendered exceeds one year at the effective time of the Reverse Stock Split. The deductibility of capital losses is subject to limitations. A U.S. holder that receives cash in lieu of a fractional Common Share pursuant to the Reverse Stock Split and whose proportionate interest in us is not reduced (after taking into account certain constructive ownership rules) should generally be treated as having received a distribution that will be treated first as dividend income to the extent paid out of our current or accumulated earnings and profits, and then as a tax-free return of capital to the extent of the U.S. holder’s tax basis in our Common Shares, with any remaining amount being treated as capital gain. U.S. holders should consult their tax advisors regarding the tax effects to them of receiving cash in lieu of fractional shares based on their particular circumstances.

Non-U.S. Holders

Generally, non-U.S. holders will not recognize any gain or loss as a result of the Reverse Stock Split. In particular, gain or loss will not be recognized with respect to a non-U.S. holder that receives cash in lieu of a fractional Common Share and whose proportionate interest in us is reduced (after taking into account certain constructive ownership rules) provided that (a) such gain or loss is not effectively connected with the conduct of a trade or business by such non-U.S. holder in the United States (or, if certain income tax treaties apply, is not attributable to a non-U.S. holder’s permanent establishment in the United States), (b) with respect to a non-U.S. holder who is an individual, such non-U.S. holder is present in the United States for less than 183 days in the taxable year of the Reverse Stock Split and other conditions are met, and (c) such non-U.S. holder complies with certain certification requirements. If such gain is effectively connected with the non-U.S. holder’s conduct of a trade or business in the U.S., and if an applicable income tax treaty so provides, the gain is attributable to a permanent establishment or fixed base maintained by the non-U.S. holder in the United States, the non-U.S. holder will be taxed on a net income basis at the regular tax rates and in the manner applicable to U.S. holders, and if the non-U.S. holder is a corporation, an additional branch profits tax at a rate of 30%, or a lower rate as may be specified by an applicable income tax treaty, may also apply. If the non-U.S. holder is an individual present in the United States for 183 days or more in the taxable year of the Reverse Stock Split and certain other requirements are met, the non-U.S. holder will be subject to a 30% tax (or such lower rate as may be specified by an applicable income tax treaty between the United States and such holder’s country of residence) on the net gain from the exchange of the Common Shares, which may be offset by certain U.S.-source capital losses of the non-U.S. holder, if any.

Notwithstanding the foregoing, with respect to a non-U.S. holder that receives cash in lieu of a fractional Common Share pursuant to the Reverse Stock Split and whose proportionate interest in us is not reduced (after taking into account certain constructive ownership rules), the gain will be treated as a dividend rather than capital gain to the extent of the non-U.S. holder’s ratable share of our current or accumulated earnings and profits as calculated for U.S. federal income tax purposes, then as a tax-free return of capital to the extent of (and in reduction of) the non-U.S. holder’s aggregate adjusted tax basis in the shares, and any remaining amount will be treated as capital gain.

We will withhold U.S. federal income taxes equal to 30% of any cash payments made to a non-U.S. holder as a result of the Reverse Stock Split that may be treated as a dividend, unless such holder properly demonstrates that a reduced rate of U.S. federal income tax withholding or an exemption from such withholding is applicable. For example, an applicable income tax treaty may reduce or eliminate U.S. federal income tax withholding, in which case a non-U.S. holder claiming a reduction in (or exemption from) such tax must provide us with a properly completed IRS Form W-8BEN (or other appropriate IRS Form W-8) claiming the applicable treaty benefit. Alternatively, an exemption generally should apply if the non-U.S. holder’s gain is effectively connected with a U.S. trade or business of such holder, and such holder provides us with an appropriate statement to that effect on a properly completed IRS Form W-8ECI.

Non-U.S. holders should consult their own tax advisors regarding possible dividend treatment and should consult their own tax advisor regarding the U.S. federal, state, local, and foreign income and other tax consequences of the Reverse Stock Split.

Information Reporting and Backup Withholding

Cash payments received by a U.S. holder of Common Shares pursuant to the Reverse Stock Split may be subject to information reporting and may be subject to U.S. backup withholding (currently at 24%) unless such holder provides proof of an applicable exemption or a correct taxpayer identification number and otherwise complies with the applicable requirements of the backup withholding rules. In general, backup withholding and information reporting will not apply to payment of cash in lieu of a fractional Common Share to a non-U.S. holder pursuant to the Reverse Stock Split if the non-U.S. holder certifies under penalties of perjury that it is a non-U.S. holder, and the applicable withholding agent does not have actual knowledge to the contrary. In certain circumstances the amount of cash paid to a non-U.S. holder in lieu of a fractional Common Share, the name and address of the beneficial owner and the amount, if any, of tax withheld may be reported to the IRS. Any amount withheld under the U.S. backup withholding rules is not an additional tax and will generally be allowed as a refund or credit against the U.S. holder’s U.S. federal income tax liability provided that the required.

FATCA

Under the Foreign Account Tax Compliance Act (“FATCA”), withholding taxes may apply to certain types of payments made to “foreign financial institutions” (as specially defined in the Code) and certain other non-United States entities. Specifically, a 30% withholding tax may be imposed on dividends on stock paid to a foreign financial institution or to a non-financial foreign entity, unless (1) the foreign financial institution undertakes certain diligence and reporting, (2) the non-financial foreign entity either certifies it does not have any substantial United States owners or furnishes identifying information regarding each substantial United States owner, or (3) the foreign financial institution or non-financial foreign entity otherwise qualifies for an exemption from these rules. If the payee is a foreign financial institution and is subject to the diligence and reporting requirements in clause (1) above, then, pursuant to an agreement between it and the U.S. Treasury or an intergovernmental agreement between, generally, the jurisdiction in which it is resident and the U.S. Treasury, it must, among other things, identify accounts held by certain United States persons or United States-owned foreign entities, annually report certain information about such accounts and withhold 30% on payments to non-compliant foreign financial institutions and certain other account holders.

Any cash paid to a non-U.S. holder as a result of the Reverse Stock Split that is treated as dividend may be subject to withholding under FATCA unless the requirements set forth above are satisfied (if applicable) and appropriate certifications are made. While withholding under FATCA would have applied also to payments of gross proceeds from the sale or other disposition of our Common Shares on or after January 1, 2019, proposed Treasury Regulations eliminate FATCA withholding on payments of gross proceeds entirely. Taxpayers generally may rely on these proposed Treasury Regulations until final Treasury Regulations are issued.

Interests of Directors and Executive Officers

Our directors and executive officers have no substantial interests, directly or indirectly, in the matters set forth in this proposal except to the extent of their ownership of our Common Shares.

Required Vote

The affirmative vote of the holders of a special majority (being not less than two-thirds) of the votes cast on this Reverse Stock Split Proposal (Proposal 1) at the Special Meeting will be required to approve this proposal. Abstentions and broker non-votes are not votes cast and therefore will have no effect on the outcome of this proposal.

THE BOARD UNANIMOUSLY RECOMMENDS A VOTE
“FOR” APPROVAL OF THE REVERSE STOCK SPLIT PROPOSAL.

PROPOSAL 2

APPROVAL OF THE Share Issuance PROPOSAL

Purpose and Background of the Share Issuance Proposal

Pursuant to the terms of a Securities Purchase Agreement that we entered into on November 13, 2024 (the “Purchase Agreement”) with certain institutional investors (collectively, the “Investors”), we agreed to issue, in a registered direct offering (the “Offering”), common share warrants (the “Warrants”) to purchase up to 1,666,667 common shares, to the Investors at a purchase price of $ 0.01 per warrant. These Warrants are be exercisable six months from the issuance at an exercise price of $0.60 per share and will expire 5.5 years from the date of issuance.

We received net proceeds from the Offering of approximately $1.0 million, before deducting placement agent fees and other offering expenses payable by the Company and excluding the net proceeds, if any, from the exercise of the placement agent warrants. D. Boral Capital LLC (“D. Boral”) acted as placement agent in the Offering. In connection with the closing of the Offering, we paid a placement fee of $[*]  to D. Boral, equal to 7.0% of the gross proceeds of the Offering paid to us, and a 0.5% management fee of the gross proceeds.

The Warrants expire 5.5 years from their date of issuance. The Warrants are exercisable, six months from the issuance, for up to an aggregate of 1,666,667 Common Shares (“Warrant Shares”) at an exercise price equal to $0.60 (the “Exercise Price”), subject to adjustment for any stock splits, stock dividends, recapitalizations, and similar events. The Warrants provide for cashless exercise under certain circumstances.

The number of Common Shares that may be issued upon exercise of the Warrants, and inclusive of any shares issuable under and in respect of the Purchase Agreement, is subject to an exchange cap (the “Exchange Cap”) of [*] shares, which is [*]% of the outstanding number of Common Shares on the Closing Date, unless we obtain approval from our stockholders to issue Common Shares to the holders upon exercise of the Warrants in excess of the Exchange Cap. In addition, under the terms of the Warrants, the Investors may not exercise the Warrants to the extent such exercise would cause such Investor, together with its affiliates and attribution parties, to beneficially own a number of Common Shares that would exceed 4.99% (or at the election of an Investor pursuant to the terms of its Warrant, as applicable, up to 9.99%) of our then outstanding Common Shares following such exercise.

Our Common Shares are currently listed on the NYSE American and, as such, we are subject to the rules set forth in the Guide. Section 713 of the Guide requires stockholder approval when additional shares will be issued in connection with a transaction involving the sale, issuance or potential issuance by an issuer of Common Shares (or securities convertible into Common Shares) equal to 20% or more of presently outstanding stock for less than the greater of book or market value or when the issuance or potential issuance of additional shares will result in a change of control of the issuer. The $0.60 Exercise Price as initially in effect are less than the book value on the date of issuance of the Warrants. As noted above, the number of Warrant Shares that may be issued upon exercise of the Warrants shall be limited to the [*] Exchange Cap, unless stockholder approval to exceed the Exchange Cap is obtained. Therefore, we are asking stockholders to approve the issuance of more than 20% of our issued and outstanding Common Shares as of November 13, 2024 pursuant to the Purchase Agreement, upon the exercise of the Warrants.

The Warrants provide for the Exercise Price, respectively, to be adjusted in various circumstances. We may be required to adjust the Exercise Price pursuant to the Warrants or pursuant to a modification or amendment thereto, subject to the rules of the NYSE American or other applicable law. To the extent that the Exercise Price of the Warrants is reduced, the gross proceeds received by us for the Warrant Shares may be less than anticipated. Accordingly, we are asking stockholders to approve the issuance of up to an aggregate of 1,666,667 Common Shares upon the exercise of the Warrants at the initial Exercise Price as well as an unknown lower Exercise Price in effect at the time of any such future exercise.

The Board is not seeking the approval of our stockholders to authorize our entry into the Purchase Agreement, as we already entered into the Purchase Agreement on November 13, 2024. We are only asking for approval to issue to the Investors, pursuant to the Purchase Agreement, more than 20% of our issued and outstanding Common Shares as of November 13, 2024 (the date we entered into the Purchase Agreement), upon the exercise of the Warrants.

Potential Consequences if the Share Issuance Proposal is Not Approved

The failure of our stockholders to approve the Share Issuance Proposal will mean that: (i) we cannot permit the full exercise of the Warrants, and (ii) we may incur substantial additional costs and expenses.

Potential Adverse Effects of the Approval of the Share Issuance Proposal

If the Share Issuance Proposal is approved, existing stockholders will suffer dilution in their ownership interests in the future upon the issuance of the Common Shares upon exercise of the Warrants. In addition, the sale into the public market of these shares could materially and adversely affect the market price of our Common Shares.

Vote Required

The affirmative vote of the holders of a simple majority (being not less than one-half) of the votes cast on this Share Issuance Proposal (Proposal 2) at the Special Meeting will be required to approve this proposal. Abstentions and broker non-votes are not votes cast and therefore will have no effect on the outcome of this proposal.

THE BOARD UNANIMOUSLY RECOMMENDS A VOTE
“FOR” APPROVAL OF THE SHARE ISSUANCE PROPOSAL.

PROPOSAL 3

APPROVAL OF THE ADJOURNMENT PROPOSAL

Purpose and Background of the Adjournment Proposal

The Board believes that if at the Special Meeting the number of votes represented by our Common Shares present or represented and voting in favor is insufficient to approve the Reverse Stock Split Proposal or the Share Issuance Proposal, it is in the best interests of the stockholders to enable the Board to continue to seek to obtain a sufficient number of additional votes to approve the Reverse Stock Split Proposal or the Share Issuance Proposal.

In this Adjournment Proposal, we are asking stockholders to authorize the holder of any proxy solicited by the Board to vote in favor of adjourning or postponing the Special Meeting or any adjournment or postponement thereof. If our stockholders approve this proposal, we could adjourn or postpone the Special Meeting, and any adjourned session of the Special Meeting, to use the additional time to solicit additional proxies in favor of the Reverse Stock Split Proposal or the Share Issuance Proposal.

Additionally, approval of the Adjournment Proposal could mean that, in the event we receive proxies indicating that holders of a requisite majority of the number of votes cast will vote against the Reverse Stock Split Proposal or the Share Issuance Proposal, we could adjourn or postpone the Special Meeting without a vote on the Reverse Stock Split Proposal or the Share Issuance Proposal and use the additional time to solicit the holders of those shares to change their vote in favor of the Reverse Stock Split Proposal or the Share Issuance Proposal.

Vote Required

The affirmative vote of the holders of a simple majority (being not less than one-half) of the votes cast on this Adjournment Proposal (Proposal 3) at the Special Meeting will be required to approve this proposal. Abstentions and broker non-votes are not votes cast and therefore will have no effect on the outcome of this proposal.

THE BOARD UNANIMOUSLY RECOMMENDS A VOTE
“FOR” APPROVAL OF THE ADJOURNMENT PROPOSAL.

SECURITY OWNERSHIP OF MANAGEMENT AND
CERTAIN BENEFICIAL OWNERS

The following table sets forth information with respect to the beneficial ownership of our Common Shares, as of the Record Date:

The following table sets forth information, as of the Record Date, or as otherwise set forth below, with respect to the beneficial ownership of our Common Shares (i) all persons known to us to be the beneficial owners of more than 5% of the outstanding Common Shares, (ii) each of our directors and our executive officer named in the Summary Compensation Table, and (iii) all of our directors and our current executive officer as a group. As of the Record Date, we had Common Shares outstanding.

Unless otherwise indicated the mailing address of each of the stockholders below is c/o Pineapple Financial Inc., Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3RI. Except as otherwise indicated, and subject to applicable community property laws, except to the extent authority is shared by both spouses under applicable law, the Company believes the persons named in the table have sole voting and investment power with respect to all Common Shares held by them.

* Less than 1%

NOTICE REGARDING DELIVERY OF STOCKHOLDER DOCUMENTS
(“HOUSEHOLDING” INFORMATION)

The SEC has adopted rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery requirements for proxy statements and annual reports by delivering a single copy of these materials to an address shared by two or more Pineapple stockholders. This process, which is commonly referred to as “householding,” potentially means extra convenience for stockholders and cost savings for companies and intermediaries. A number of brokers and other intermediaries with account holders who are our stockholders may be householding our stockholder materials, including this proxy statement. In that event, a single proxy statement, as the case may be, will be delivered to multiple stockholders sharing an address unless contrary instructions have been received from the affected stockholders. Once you have received notice from your broker or other intermediary that it will be householding communications to your address, householding will continue until you are notified otherwise or until you revoke your consent, which is deemed to be given unless you inform the broker or other intermediary otherwise when you receive or received the original notice of householding. If, at any time, you no longer wish to participate in householding and would prefer to receive a separate proxy statement, please notify your broker or other intermediary to discontinue householding and direct your written request to receive a separate proxy statement to us at: Pineapple Financial Inc., Attention: Corporate Secretary, Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1 or by calling us at (416) 669-2046. Stockholders who currently receive multiple copies of the proxy statement at their address and would like to request householding of their communications should contact their broker or other intermediary.

STOCKHOLDER PROPOSALS FOR THE 2026 ANNUAL MEETING

For any proposal to be considered for inclusion in our proxy statement and form of proxy for submission to the stockholders at our 2026 Annual Meeting of Stockholders, it must be submitted in writing and comply with the requirements of Rule 14a-8 of the Exchange Act. Such proposals must be received by the Company at its offices at Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1, no later than December 29, 2025.

If we are not notified of a stockholder proposal within a reasonable time prior to the time we send our proxy statement for our 2026 Annual Meeting of Stockholders, our Board will have discretionary authority to vote on the stockholder proposal, even though the stockholder proposal is not discussed in the proxy statement. In order to curtail any controversy as to the date on which a stockholder proposal was received by us, it is suggested that stockholder proposals be submitted by certified mail, return receipt requested, and be addressed to PINEAPPLE FINANCIAL INC., Unit 200, 111 Gordon Baker Road, Toronto, Ontario M2H 3R1. Notwithstanding, the foregoing shall not affect any rights of stockholders to request inclusion of proposals in our proxy statement pursuant to Rule 14a-8 under the Exchange Act nor grant any stockholder a right to have any nominee included in our proxy statement.