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                            September 25, 2023

       Shubha Dasgupta
       Chief Executive Officer
       Pineapple Financial Inc.
       Unit 200, 111 Gordon Baker Road
       North York, Ontario M2H 3R1

                                                        Re: Pineapple Financial
Inc.
                                                            Amendment No. 5
Registration Statement on Form S-1
                                                            Filed on September
15, 2023
                                                            File No. 333-268636

       Dear Shubha Dasgupta:

             We have reviewed your amended registration statement and have the
following
       comments. In some of our comments, we may ask you to provide us with
information so we
       may better understand your disclosure.

              Please respond to this letter by amending your registration
statement and providing the
       requested information. If you do not believe our comments apply 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 these comments, we may have additional comments.

       Amendment No. 5 to Registration Statement on Form S-1

       Management's Discussion and Analysis of Financial Condition and Results
of Operations
       Economic Review, page 26

   1.                                                   Please revise your
filing to update your Economic Review discussion related to the
                                                        Canadian real estate
market (i.e. home sales and purchase mortgage sales) and the
                                                        Canadian prime rate to
discuss the current economic environment for 2023. For instance,
                                                        we note that the
Canadian prime rate is currently 7.20%. Additionally, please revise your
                                                        filing to clearly
explain how the current Canadian real estate market has impacted your
                                                        financial results for
the nine-months ended May 31, 2023, and is expected to impact future
                                                        periods.
 Shubha Dasgupta
FirstName  LastNameShubha   Dasgupta
Pineapple Financial Inc.
Comapany 25,
September  NamePineapple
               2023        Financial Inc.
September
Page 2     25, 2023 Page 2
FirstName LastName
Comparison of the Nine Months Ended May 31, 2023 and 2022, page 30

2.       We note disclosure on pages 1, 7, 29 and 30 that    net revenue    was
$1,937,923,
         $2,775,043, $3,600,851, and $2,983,717 for the nine months ended May
31, 2023 and
         2022 and the years ended August 31, 2022 and 2021, respectively. We
also note
         disclosure on pages 30, F-16 and F-45 that these same amounts
represent    total revenue.
         Please revise to provide consistent disclosure of either "net revenue"
or "total revenue"
         throughout your filing.
Selling, General and Administrative Expenses, page 31

3.       We note that your table on page 31 appears to detail total expenses
rather than selling,
         general and administrative services as labeled. Please revise your
disclosure accordingly.
4.       We note your disclosure that office and general expenses increased by
47.44% due to an
         increase in agents is inconsistent with the table on page 31 showing
that office and general
         expenses decreased by 47.44%. Please revise your disclosure
accordingly.
Executive and Director Compensation, page 55

5.       Please update the executive compensation disclosure for fiscal year
end 2023, as August
         31, 2023 appears to be your last completed fiscal year. Refer to Item
402 of Regulation S-
         K and Question 117.05, Compliance & Disclosure Interpretations of
Regulation S-K,
         available on our website at www.sec.gov.
Note 17. Subsequent Events, page F-16

6.       We note your disclosure stating that on July 6, 2023 you completed a
reverse stock split of
         your issued and outstanding Common Shares at a ratio of 1-for-3.9.
Please revise your
         filing to ensure that all share information in the filing, including
the information included
         in your historical consolidated financial statements for each of the
years ended August 31,
         2022 and 2021, retroactively reflects this reverse stock split in
accordance with ASC 260-
         10-55-12 and ASC 505-10-S99-4. In addition, please have your auditors
dual date their
         report for the impact of the stock split.
Exhibits

7.       We note that you currently refer to Scichenzia Ross Ference LLP in the
legal matters
         section, and in your prior amendment you included the legality opinion
of Scichenzia
         Ross Ference LLP as an exhibit to the registration statement. Please
advise why it is no
         longer included in the exhibit index or filed as an exhibit to the
registration statement. We
         also note that the legal opinion filed will need to opine that the
warrants are your legal
         obligations. Refer to Staff Legal Bulletin No. 19, Legality and Tax
Opinions in Registered
         Offerings, available on our website at www.sec.gov.
       You may contact John Spitz at 202-551-3484 or Ben Phippen at
202-551-3697 if you
have questions regarding comments on the financial statements and related
matters. Please
 Shubha Dasgupta
Pineapple Financial Inc.
September 25, 2023
Page 3

contact Susan Block at 202-551-3210 or Tonya K. Aldave at 202-551-3601 with any
other
questions.



                                                        Sincerely,
FirstName LastNameShubha Dasgupta
                                                        Division of Corporation
Finance
Comapany NamePineapple Financial Inc.
                                                        Office of Finance
September 25, 2023 Page 3
cc:       Darrin Ocasio, Esq.
FirstName LastName