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                              October 26, 2022

       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. 1 to
                                                            Draft Registration
Statement on Form S-1
                                                            Submitted on
October 12, 2022
                                                            CIK No. 0001938109

       Dear Shubha Dasgupta:

             We have reviewed your amended draft 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 providing the requested
information and either submitting
       an amended draft registration statement or publicly filing your
registration statement on
       EDGAR. 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 the information you provide in response to these
comments and your
       amended draft registration statement or filed registration statement, we
may have additional
       comments.

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

       Prospectus Summary, page 1

   1.                                                   We note your response
to our prior comment 1 and reissue in part. Please revise the
                                                        summary section to
disclose your multiple class share structure (Common Shares, Class A
                                                        Shares, Class B Shares,
and Class C Shares).
       Risk Factors
       We are dependent on the residential real estate market, page 8

   2.                                                   We note your risk
factor disclosure here that your financial performance is closely
                                                        connected to the
strength of the residential real estate market, and then you list some
 Shubha Dasgupta
FirstName  LastNameShubha Dasgupta
Pineapple Financial Inc.
Comapany
October 26,NamePineapple
            2022         Financial Inc.
October
Page 2 26, 2022 Page 2
FirstName LastName
         business and macroeconomic conditions, such as ecomonic slowdown and
higher interest
         rates. Please revise your risk factor to clarify if any of those
discussed potential
         macroeconomic conditions are currently adversely impacting the real
estate market and
         your business, and to what extent, so that investors may assess the
risk. Further, we note
         your disclosure regarding policies of the U.S. Federal Reserve Board.
Please clarify how
         the U.S. federal monetary policy affects you and also discuss how
Canadian monetary
         policies are affecting your business.
Increases in interest rates may have an adverse effect on our business, page 12

3.       We note your response to our prior comment 7 and reissue in part.
Please revise your
         discussion in the risk factor to clarify where in the cycle interest
rates are and how the
         rising interest rate environment is impacting your business.
Use of Proceeds, page 22

4.       We note your response to our prior comment 10 and reissue in part. We
note that
         approximately 20% of the use of proceeds may go to expansion,
including acquisitions.
         Please identify the businesses or nature of business sought and the
status of the
         negotiations. If you do not have any current acquisition plans, please
clarify that.
Management's Discussion and Analysis of Finanical Condition, page 26

5.       We note your response to our prior comment 11 and reissue in part.
Following the
         language you revised in response to our comment, please clarify what
"[t]his" is referring
         to in the beginning of the sentence, "[t]his has been primarily due to
organic growth,"
         found on page 27. We further note your revision here to include the
different categories
         of "Users." We note the term here appears to include consumers,
whereas the same
         defined term in your summary on page 1 does not appear to include
consumers. We
         further note thtat in the business section on page 33 the total amount
of agents is 627 -- the
         same number as the total numbr of Users found on page 27 -- which
seems to include
         agents and consumers. As such, please revise throughout to
consistently define "Users."
Business
Insuarance Products, page 35

6.       We note your responses to our prior comment 13 and that your insurance
business is in the
         early stages of development and also your disclosure regarding the
insurance services
         Pineapple Insurance provides. Please clarify if some of the insurance
offered is offered
         through third parties. Discuss the material steps, costs anticipated,
whether financing will
         be needed, and the timeline for growing Pineapple Insurance from its
early stages of
         development. In addition, add appropriate risk factor disclosure and a
section describing
         insurance regulation in Canada.
7.       We note your response to prior comment 14. Please also explain in the
prospectus, as you
         have in your response, that as a regulatory requirement, all Canadian
mortgage approvals
 Shubha Dasgupta
Pineapple Financial Inc.
October 26, 2022
Page 3
       being presented by the mortgage broker channel must include the option
for a client to
       consider certain insurance options.
Principal Shareholders, page 58

8.     We note your response to our prior comment 17 and reissue in part.
Please update the
       principal shareholders table to provide ownership as of the most recent
practicable date. In
       this regard, we note that the table is currently as of May 31, 2022.
Refer to Item 403 of
       Regulation S-K.
Description of Securities
Warrants, page 61

9.     We note your response to our prior comment 20 and reissue in part.
Please revise to
       explain how the exercise price is calculated by explaining what you mean
by "based on
       1.5 times the common share price issued."
       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
contact Susan Block at 202-551-3210 or Tonya Aldave at 202-551-3601 with any
other
questions.



                                                             Sincerely,
FirstName LastNameShubha Dasgupta
                                                             Division of
Corporation Finance
Comapany NamePineapple Financial Inc.
                                                             Office of Finance
October 26, 2022 Page 3
cc:       Darrin Ocasio, Esq.
FirstName LastName