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June 17, 2024
Shubha Dasgupta
Chief Executive Officer
Pineapple Financial Inc.
Unit 200, 111 Gordon Baker Road
North York, Ontario M2H 3R1
Re:Pineapple Financial Inc.
Registration Statement on Form S-1
Filed May 29, 2024
File No. 333-279802
Dear Shubha Dasgupta:
            We have conducted a limited review of your registration statement and have the
following comments.
            Please respond to this letter by amending your registration statement and providing the
requested information. If you do not believe a comment applies to your facts and circumstances
or do not believe an amendment is appropriate, please tell us why in your response.
            After reviewing any amendment to your registration statement and the information you
provide in response to this letter, we may have additional comments.
Form S-1 filed May 29, 2024
General
1.We note your disclosure on the cover page and on page 64 that the selling shareholder
"may be" considered or deemed an underwriter within the meaning of the Securities
Act. Since the selling stockholder, Brown Stone Capital Ltd, is the equity line investor
under your Equity Purchase Agreement dated May 10, 2024, please revise to disclose that
the selling shareholder is an underwriter. Refer to Securities Act C&DI 139.13.
Prospectus Summary, page 1
2.Please revise your prospectus summary to describe the material terms of the Equity
Purchase Agreement and Securities Purchase Agreement in greater detail, including
material conditions under which the company may access the funds available under such
agreements. Further, disclose the maximum number of your common shares that can be
issued under the equity line agreement, and clearly describe and

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 Comapany NamePineapple Financial Inc.
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 FirstName LastNameShubha Dasgupta
Pineapple Financial Inc.
June 17, 2024
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quantify the dilutive effect of the formula or pricing mechanics on your share price as the
result of the equity line purchase agreement. Finally, briefly discuss the impact of
the equity line on your business.
3.We note that your share price has declined since your initial public offering. We further
note that the company's share price has continued to decline since the signing of the equity
purchase agreement. Revise your summary to provide a tabular presentation of the
possible dilutive impact on the public share price if the $15m that you can sell to the
purchasers under the agreement were to become available. For instance, show the cost to
the purchaser of shares at a range of market prices since the agreement was negotiated. In
particular, please note the market price below which you would not be able to put shares
to the purchaser under the equity purchase agreement without filing a new registration
statement. Make conforming changes to the risk factor on page 20.
Risk Factors, page 8
4.Please add a separately captioned risk factor identifying risks to shareholders related to
your equity line agreement with Brown Stone Capital Ltd. Discuss the price discount at
which you would sell shares to Brown Stone Capital Ltd. and the dilutive effect and
impact on market price from selling shares at a discount and from the resales of these
securities to the public.
If we fail to maintain compliance with the continued listing requirements of the NYSE
American, page 20
5.Revise this risk factor, and other relevant risk factors, to discuss your most recent share
price, and the minimum share price that you must maintain in order to meet NYSE
American listing standards.
Plan of Distribution, page 63
6.We note your disclosure that your selling securityholders may sell their securities in one
or more underwritten offerings on a firm commitment or best efforts basis. Please confirm
your understanding that the retention by a selling stockholder of an underwriter would
constitute a material change to your plan of distribution requiring a post-effective
amendment. Refer to your undertaking provided pursuant to Item 512(a)(1)(iii) of
Regulation S-K.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration. Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.

 FirstName LastNameShubha Dasgupta
 Comapany NamePineapple Financial Inc.
 June 17, 2024 Page 3
 FirstName LastName
Shubha Dasgupta
Pineapple Financial Inc.
June 17, 2024
Page 3
            Please contact John Stickel at 202-551-3324 or Christian Windsor at 202-551-3419 with
any other questions.
Sincerely,
Division of Corporation Finance
Office of Finance