SecProbe.io

CORRESP
 1
 filename1.htm

 PINEAPPLE
FINANCIAL INC.

 Unit
200 111 Gordon Baker Road

 Toronto,
Ontario M2H 3R1

 Tel:
(416) 669-2046

 September
29, 2025

 VIA
EDGAR

 Robert
Arzonetti

 Division
of Corporation Finance

 Securities
and Exchange Commission

 100
F Street, NE

 Washington,
D.C. 20549

 Re:
 Re:
 Pineapple Financial Inc.

 Preliminary
 Proxy Statement on Schedule 14A
 Filed
 September 19, 2025
 File
 No. 001-41738

 Dear
Mr. Arzonetti,

 On
behalf of Pineapple Financial Inc. (the "Company"), this letter responds to comments provided by the staff of the Division
of Corporation Finance (the "Staff"), of the Securities and Exchange Commission (the "Commission") provided to
the undersigned on September 26, 2025, regarding the Company's Preliminary Proxy Statement on Schedule 14A (the "Proxy Statement"),
which was submitted to the Commission on September 19, 2025.

 For
convenience, the Staff's comments have been restated below and the Company's responses are set out immediately under the
restated comments. A revised preliminary proxy statement on Schedule 14A ("Amendment No. 1.") reflecting changes made in
response to the Staff's comments, along with changes made to update certain other information in the Proxy Statement, has also
been submitted on this date. Unless otherwise indicated, defined terms used herein have the meanings set forth in the Proxy Statement.

 Preliminary
Proxy Statement on Schedule 14A

 General

 1.
We note from your Form 8-K filed on September 10, 2025 and related press release that the Injective Foundation, as part of the subscription
receipt financing, has been granted review rights with respect to the escrow release process pursuant to a Side Letter Agreement. Your
proxy statement does not describe these rights or the Foundation's role in connection with the INJ treasury. Please revise your
disclosure to describe the nature of these rights, the Foundation's involvement, and the scope of authority or influence it may
have over the administration of the INJ treasury. In addition, please clarify whether the company has established or plans to establish
any board, committee, or advisory group to oversee the treasury strategy and, if so, whether investors such as the Injective Foundation
or other participants will have representation or appointment rights.

 Response:
The Company acknowledges the Staff's comment and has revised the Proxy Statement to include the review rights pursuant to the Side
Letter Agreement, the Foundation's role in connection with the INJ treasury, and the board appointment. Please see under the heading
" Proposal 1- Purpose and Background of the Share Issuance Proposal" of Amendment No. 1.

 2.
Please revise your disclosure to clarify that some of the investors who will acquire shares as a result of the offering,
including investors associated with the Injective Foundation, may have interests that differ from those of existing shareholders.

 Response:
The Company acknowledges the Staff's comment and has revised the Proxy Statement to clarify that some of the investors who will
acquire shares as a result of the offering, including investors associated with the Injective Foundation, may have interests that differ
from those of existing shareholders. Please see under the heading " interests of certain persons or companies in matters to be
acted upon" and " interests of informed persons in material transactions" of Amendment No. 1.

 The
Company hereby acknowledges that it is responsible for the adequacy and accuracy of the disclosures.

 If
you have any questions, please do not hesitate to contact Matthew Siracusa, Esq., of Sichenzia Ross Ference Carmel LLP, at msiracusa@SRFC.LAW
or (845) 649-8868.

 Very
 truly yours,

 /s/
 Darrin M Ocasio

 Darrin
 M Ocasio

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 September 29, 2025

Shubha Dasgupta
Chief Executive Officer
Pineapple Financial Inc.
Unite 200, 111 Gordon Baker Road
Toronto, Ontario M2H 3R1

 Re: Pineapple Financial Inc.
 Revised Preliminary Proxy Statement on Schedule 14A
 Filed September 29, 2025
 File No. 001-41738
Dear Shubha Dasgupta:

 We have completed our review of your filing. 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.

 Sincerely,

 Division of Corporation
Finance
 Office of Finance
cc: Darrin M. Ocasio, Esq.
</TEXT>
</DOCUMENT>

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 September 26, 2025

Shubha Dasgupta
Chief Executive Officer
Pineapple Financial Inc.
Unite 200, 111 Gordon Baker Road
Toronto, Ontario M2H 3R1

 Re: Pineapple Financial Inc.
 Preliminary Proxy Statement on Schedule 14A
 Filed September 19, 2025
 File No. 001-41738
Dear Shubha Dasgupta:

 We have reviewed your filing and have the following comments.

 Please respond to this letter within ten business days by providing the
requested
information or advise us as soon as possible when you will respond. If you do
not believe a
comment applies to your facts and circumstances, please tell us why in your
response.

 After reviewing your response to this letter, we may have additional
comments.

Preliminary Proxy Statement on Schedule 14A
General

1. We note from your Form 8-K filed on September 10, 2025 and related press
release
 that the Injective Foundation, as part of the subscription receipt
financing, has been
 granted review rights with respect to the escrow release process
pursuant to a Side
 Letter Agreement. Your proxy statement does not describe these rights or
the
 Foundation's role in connection with the INJ treasury. Please revise
your disclosure to
 describe the nature of these rights, the Foundation's involvement, and
the scope of
 authority or influence it may have over the administration of the INJ
treasury. In
 addition, please clarify whether the company has established or plans to
establish any
 board, committee, or advisory group to oversee the treasury strategy
and, if so,
 whether investors such as the Injective Foundation or other participants
will have
 representation or appointment rights.
 September 26, 2025
Page 2
2. Please revise your disclosure to clarify that some of the investors who
will acquire
 shares as a result of the offering, including investors associated with
the Injective
 Foundation, may have interests that differ from those of existing
shareholders.

 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.

 Please contact Robert Arzonetti at 202-551-8819 or Christian Windsor at
202-551-
3419 with any other questions.

 Sincerely,

 Division of
Corporation Finance
 Office of Finance
cc: Darrin M. Ocasio, Esq.
</TEXT>
</DOCUMENT>

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 filename1.htm

 PINEAPPLE
FINANCIAL INC.

 Unit
200, 111 Gordon Baker Road

 North
York, Ontario M2H 3R1

 May
1, 2025

 Securities
and Exchange Commission

 Division
of Corporation Finance

 100
F Street N.E.

 Washington,
D.C. 20549

 Attention:
Aisha Adegbuyi

 Re:
 Pineapple
 Financial Inc.

 Registration
 Statement on Form S-1

 Submitted
 April 25, 2025

 Ladies
and Gentlemen:

 Pursuant
to Rule 461 promulgated under the Securities Act of 1933, as amended, Pineapple Financial Inc. (the "Company") hereby requests
acceleration of the effectiveness of the above-referenced Registration Statement, so that such Registration Statement will become effective
as of 5:00 p.m. Eastern time, Thursday, May 1, 2025, or as soon as practicable thereafter.

 Very
 truly yours,

 PINEAPPLE
 FINANCIAL INC.

 By:

 /s/
 Shubha Dasgupta

 Shubha
 Dasgupta

 Chief
 Executive Officer

CORRESP
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 D. Boral Capital LLC

 590 Madison Avenue, 39 th Floor

 New York, NY 10022

 May 1, 2025

 VIA EDGAR

 U.S. Securities and Exchange Commission

 Division of Corporation Finance

 100 F Street, N.E.

 Washington, DC 20549

 Attention: Aisha Adegbuyi

 Re: Pineapple Financial Inc.

 Registration Statement on Form S-1

 File No. 333-286783

 REQUEST FOR ACCELERATION OF EFFECTIVENESS

 Requested Date: Thursday, May 1,
2025

 Requested Time: 5:00 p.m., Eastern
Time

 Ladies and Gentlemen:

 Pursuant to Rule 461 under the
Securities Act of 1933, as amended (the "Securities Act"), we, the undersigned, as the sole placement agent for the proposed
public offering on a best efforts basis of securities of Pineapple Financial Inc. (the "Company"), hereby join the Company's
request that the effective date of the above-referenced registration statement on Form S-1 be accelerated so that it will be declared
effective at 5:00 p.m., Eastern Time, on Thursday, May 1, 2025, or as soon thereafter as possible.

 Pursuant to Rule 460 under the
Securities Act, please be advised that we will distribute as many copies of the proposed form of preliminary prospectus as appears to
be reasonable to secure adequate distribution of the preliminary prospectus.

 The undersigned advises that it
has complied and will continue to comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

 Very truly yours,

 D. BORAL CAPITAL LLC

 By:
 /s/ Philip
 Wiederlight

 Name:
 Philip Wiederlight

 Title:
 Chief Operating Officer

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 April 16, 2025

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

 Re: Pineapple Financial Inc.
 Draft Registration Statement on Form S-1
 Submitted April 4, 2025
 CIK No. 0001938109
Dear Shubha Dasgupta:

 This is to advise you that we have not reviewed and will not review your
registration
statement.

 Please refer to Rules 460 and 461 regarding requests for acceleration.
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.

 Please contact Aisha Adegbuyi at 202-551-8754 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of Finance
cc: Darrin M. Ocasio, Esq.
</TEXT>
</DOCUMENT>

CORRESP
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PINEAPPLE
FINANCIAL INC.

Unit
200, 111 Gordon Baker Road

North
York, Ontario M2H 3R1

October
28, 2024

Securities
and Exchange Commission

Division
of Corporation Finance

100
F Street N.E.

Washington,
D.C. 20549

Attention:
Mr. Robert Arzonetti

    Re:
    Pineapple
    Financial Inc.

    Registration
    Statement on Form S-3 (as amended)

    File
    No. 333-282629

Ladies
and Gentlemen:

Pursuant
to Rule 461 promulgated under the Securities Act of 1933, as amended, Pineapple Financial Inc. (the “Company”) hereby requests
acceleration of the effectiveness of the above-referenced Registration Statement, so that such Registration Statement will become effective
as of 5:00 p.m. Eastern time, Tuesday, October 29, 2024, or as soon as practicable thereafter.

    Very
    truly yours,

    PINEAPPLE
    FINANCIAL INC.

    By:

    /s/
    Shubha Dasgupta

    Shubha
    Dasgupta

    Chief
    Executive Officer

October 23, 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-3
Filed October 15, 2024
File No. 333-282629
Dear Shubha Dasgupta:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration. 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.
            Please contact Robert Arzonetti at 202-551-8819 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:Darrin M. Ocasio

CORRESP
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July
3, 2024

VIA
EDGAR AND FACSIMILE

United
States Securities and Exchange Commission

Division
of Corporation Finance

Office
of Finance

100
F. Street, N.E.

Washington,
D.C. 20549

Attention:
John Stickel

Re:
Pineapple Financial Inc. (the “Company”)

Registration
Statement on Form S-1

File
No. 333-279802

Ladies
and Gentlemen:

In
accordance with Rule 461 under the Securities Act of 1933, as amended, the undersigned respectfully requests that the effective date
for the Registration Statement referred to above be accelerated so that it will be declared effective at 4:30 PM EDT on Monday, July
8, 2024, or as soon thereafter as is practicable.

The
Company hereby acknowledges that:

    ●
    should
    the Commission or the staff, acting pursuant to delegated authority, declare the filing effective, it does not foreclose the Commission
    from taking any action with respect to the filing;

    ●
    the
    action of the Commission or the staff, acting pursuant to delegated authority, in declaring the filing effective, does not relieve
    the Company from its full responsibility for the adequacy and accuracy of the disclosure in the filing; and

    ●
    the
    Company may not assert this action as a defense in any proceeding initiated by the Commission or any person under the federal securities
    laws of the United States.

    Very
    truly yours,

    PINEAPPLE
    FINANCIAL INC.

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
    Dasgupta

    Title:
    Chief
    Executive Officer (Principal Executive Officer)

United States securities and exchange commission logo
June 26, 2024
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 Registration Statement on Form S-1
Filed June 20, 2024
File No. 333-279802
Dear Shubha Dasgupta:
            We have reviewed your amended registration statement and have the following comment.
            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. Unless we note otherwise,
any references to prior comments are to comments in our June 17, 2024 letter.
Amendment No. 1 to Form S-1 filed June 20, 2024
Substantial future sales of Common Shares could cause the market price of our Common Shares
to decline, page 23
1.We note your response to prior comment 4. Please 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. In this regard, we note that the Equity Purchase Agreement defines the
Purchase Price as 95% of the Market Price. Also revise to disclose this price discount in
the prospectus summary when disclosing the material terms of the agreement.

 FirstName LastNameShubha Dasgupta
 Comapany NamePineapple Financial Inc.
 June 26, 2024 Page 2
 FirstName LastName
Shubha Dasgupta
Pineapple Financial Inc.
June 26, 2024
Page 2
            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

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    June
    26, 2024

Securities
and Exchange Commission

Division
of Corporation Finance

100
F Street, NE

Washington,
D.C. 20549

Attn:
John Stickel and Christian Windsor

    Re:
    Pineapple
    Financial Inc.

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

    Filed
    June 20, 2024

    File
    No. 333-279802

Dear
John and Christian:

Please
find below our responses to the questions raised by the staff (the “Staff”) of the Securities and Exchange Commission (the
“Commission”) in its letter of comments dated June 26, 2024 (the “Comment Letter”) relating to the amendment
No. 1 to registration statement on Form S-1, which was submitted to the Commission by Pineapple Financial Inc. (the “Company”
or “we”) on June 20, 2024.

The
Company’s responses are numbered to correspond to the Staff’s comments. For your convenience, each of the Staff’s comments
contained in the Comment Letter has been restated.

We
have also updated the Registration Statement on Form S-1 (“Registration Statement”) which is submitted to the Commission
simultaneously together with this letter.

Amendment
No. 1 to Form S-1 filed June 20, 2024

Substantial
future sales of Common Shares could cause the market price of our Common Shares to decline, page 23:

    1.

    We
    note your response to prior comment 4. Please 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. In this regard, we note that the Equity Purchase Agreement defines the Purchase Price as 95% of the Market Price. Also
    revise to disclose this price discount in the prospectus summary when disclosing the material terms of the agreement..

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the pages 6 and 23 of the Registration
Statement for details.

Should
you have any questions regarding the foregoing, please do not hesitate to contact me or our counsel with any questions or comments regarding
this correspondence on the revised S-1.

    Very
    truly yours,

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
    Dasgupta

    Chief
    Executive Officer

CORRESP
1
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    June
    20, 2024

Securities
and Exchange Commission

Division
of Corporation Finance

100
F Street, NE

Washington,
D.C. 20549

Attn:
John Stickel and Christian Windsor

    Re:
    Pineapple
    Financial Inc.

    Registration
    Statement on Form S-1

    Filed
    May 29, 2024

    File
    No. 333-279802

Dear
John and Christian:

Please
find below our responses to the questions raised by the staff (the “Staff”) of the Securities and Exchange Commission (the
“Commission”) in its letter of comments dated June 17, 2024 (the “Comment Letter”) relating to the registration
statement on Form S-1, which was submitted to the Commission by Pineapple Financial Inc. (the “Company” or “we”)
on May 29, 2024.

The
Company’s responses are numbered to correspond to the Staff’s comments. For your convenience, each of the Staff’s comments
contained in the Comment Letter has been restated.

We
have also updated the Registration Statement on Form S-1 (“Registration Statement”) which is submitted to the Commission
simultaneously together with this letter.

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.

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the cover page and page 66
of the Registration Statement for details.

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 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.

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the page 6 of the Registration
Statement for details.

    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.

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the pages 8 and 9 of the Registration
Statement for details.

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.

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the page 23 of the Registration
Statement for details.

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.

Response:
We have revised the Registration Statement in accordance with the Staff’s comment. Please see the page 23 of the
Registration Statement for details.

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.

Response:
The Company acknowledges the Staff’s comment and confirms its understanding that the retention by a selling stockholder of an underwriter
would constitute a material change to the Company’s plan of distribution. In such an event, the Company will file a post-effective
amendment to the registration statement, as required under Item 512(a)(1)(iii) of Regulation S-K, to reflect this material change.

Should
you have any questions regarding the foregoing, please do not hesitate to contact me or our counsel with any questions or comments regarding
this correspondence on the revised S-1.

    Very
    truly yours,

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
    Dasgupta

    Chief
    Executive Officer

United States securities and exchange commission logo
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

 FirstName LastNameShubha Dasgupta
 Comapany NamePineapple Financial Inc.
 June 17, 2024 Page 2
 FirstName LastNameShubha Dasgupta
Pineapple Financial Inc.
June 17, 2024
Page 2
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

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October
10, 2023

VIA
EDGAR AND FACSIMILE

United
States Securities and Exchange Commission

Division
of Corporation Finance

Office
of Finance

100
F. Street, N.E.

Washington,
D.C. 20549

Attention:
Susan Block

Re:
Pineapple Financial Inc. (the “Company”)

Registration
Statement on Form S-1

File
No. 333-268636

Ladies
and Gentlemen:

In
accordance with Rule 461 under the Securities Act of 1933, as amended, the undersigned respectfully requests that the effective date
for the Registration Statement referred to above be accelerated so that it will be declared effective at 5:00 PM EDT on Thursday, October
12, 2023, or as soon thereafter as is practicable.

The
Company hereby acknowledges that:

    ●
    should the
    Commission or the staff, acting pursuant to delegated authority, declare the filing effective, it does not foreclose the Commission
    from taking any action with respect to the filing;

    ●
    the action
    of the Commission or the staff, acting pursuant to delegated authority, in declaring the filing effective, does not relieve the Company
    from its full responsibility for the adequacy and accuracy of the disclosure in the filing; and

    ●
    the Company
    may not assert this action as a defense in any proceeding initiated by the Commission or any person under the federal securities
    laws of the United States.

    Very
    truly yours,

    PINEAPPLE
    FINANCIAL INC.

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
Dasgupta

    Title:
    Chief
    Executive Officer (Principal Executive Officer)

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EF Hutton,

division of Benchmark Investments, LLC

590 Madison Avenue, 39th Floor

New York, NY 10022

October 10, 2023

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

Office of Trade & Services

100 F Street, N.E.

Washington, D.C. 20549

Re: Pineapple Financial Inc.

Registration Statement on Form S-1

File No. 333-268636

Ladies and Gentlemen:

Pursuant to Rule 461 under the Securities Act of 1933,
as amended (the “Securities Act”), we, as representative of the underwriters of the proposed public offering of securities
of Pineapple Financial Inc. (the “Company”), hereby join the Company’s request that the effective date of the above-referenced
registration statement on Form S-1, as amended, be accelerated so that it will be declared effective at 5:00 PM EDT on Thursday, October
12, 2023, or as soon thereafter as possible.

Pursuant to Rule 460 under the Securities Act, we,
as representative of the underwriters, wish to advise you that there will be distributed to each underwriter, who is reasonably anticipated
to participate in the distribution of the security, as many copies of the proposed form of preliminary prospectus as appears to be reasonable
to secure adequate distribution of the preliminary prospectus.

The undersigned advises that it has complied and will
continue to comply, and that it has been informed by the participating underwriters and dealers that they have complied with and will
continue to comply, with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

    Very truly yours,

    EF HUTTON

    division of Benchmark Investments LLC

    By:
    /s/ Sam Fleischman

    Name:
    Sam
Fleischman

    Title:
    Supervisory Principal

CORRESP
1
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PINEAPPLE
FINANCIAL INC.

Unit
200 111 Gordon Baker Road

Toronto,
Ontario M2H 3R1

Tel:
(416) 669-2046

September
27, 2023

VIA
EDGAR

Susan
Block

Division
of Corporation Finance

Securities
and Exchange Commission

100
F Street, NE

Washington,
D.C. 20549

    Re:
    Re:
    Pineapple Financial Inc.

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

    Filed
    on September 15, 2023

    File
    No. 333-268636

Dear
Ms. Block,

On
behalf of Pineapple Financial Inc. (the “Company”), this letter responds to comments provided by the staff of the Division
of Corporation Finance (the “Staff”), of the Securities and Exchange Commission (the “Commission”) provided to
the undersigned on September 25, 2023, regarding the Company’s Amendment No. 5 to the Registration Statement on Form S-1 (the “Registration
Statement”) which was submitted to the Commission on September 15, 2023.

For
convenience, the Staff’s comments have been restated below and the Company’s responses are set out immediately under the
restated comments. An amendment to the Registration Statement on Form S-1 (“Amendment No. 6”) reflecting changes made in
response to the Staff’s comments, along with changes made to update certain other information in the Registration Statement, has
also been submitted on this date. Unless otherwise indicated, defined terms used herein have the meanings set forth in the Registration
Statement.

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.

    Response:
    The Company acknowledges the Staff’s comment and has updated the Economic Review discussion to address the Staff’s comments.
    In addition, the Company has included additional disclosure to explain how the Canadian real estate market has impacted our financial
    results for the nine-months ended May 31, 2023, and how it is expected to impact future periods.

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.

    Response:
    The Company acknowledges the Staff’s comment and has revised the disclosures in Amendment No. 6 to consistently disclose the
    amounts and references for “total revenue” and “net revenue.”

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.

    Response:
    The Company acknowledges the Staff’s comment and has revised the disclosures in Amendment No. 6 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.

    Response:
    The Company acknowledges the Staff’s comment and has revised the disclosures in Amendment No. 6 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.

    Response:
    The Company acknowledges the Staff’s comment and has updated the executive compensation disclosure to include compensation
    for the year ended August 31, 2023. t

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.

    Response:
    The Company acknowledges the Staff’s comment and has revised the consolidated financial statements in Amendment No. 6 accordingly.
    In addition, the Company confirms all share information in Amendment No. 6 to reflect the reverse 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.

    Response:
    The Company acknowledges the Staff’s comment and has included the legality opinion of Sichenzia Ross Ference as Exhibit 5.2
    in Amendment No. 6.

We
thank the Staff for its review of the foregoing and the Registration Statement. If you have further comments, please feel free to contact
to our counsel, Darrin M. Ocasio., at dmocasio@srf.law or by telephone at (917) 848-6325 or Matthew Siracusa at msiracusa@srf.law, telephone
(845) 649-8868.

    Sincerely,

    /s/
    Shubha Dasgupta

    Shubha
    Dasgupta

United States securities and exchange commission logo
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.

 FirstName LastNameShubha Dasgupta
 Comapany NamePineapple Financial Inc.
 September 25, 2023 Page 2
 FirstName LastNameShubha Dasgupta
Pineapple Financial Inc.
September 25, 2023
Page 2
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

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

CORRESP
1
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July
6, 2023

VIA
EDGAR AND FACSIMILE

United
States Securities and Exchange Commission

Division
of Corporation Finance

Office
of Finance

100
F. Street, N.E.

Washington,
D.C. 20549

Attention:
Susan Block

Re:
Pineapple Financial Inc. (the “Company”)

Registration
Statement on Form S-1

File
No. 333-268636

Ladies
and Gentlemen:

In
accordance with Rule 461 under the Securities Act of 1933, as amended, the undersigned respectfully requests that the effective date
for the Registration Statement referred to above be accelerated so that it will be declared effective at 5:00 PM EDT on Thursday, July
6, 2023, or as soon thereafter as is practicable.

The
Company hereby acknowledges that:

    ●
    should
    the Commission or the staff, acting pursuant to delegated authority, declare the filing effective, it does not foreclose the Commission
    from taking any action with respect to the filing;

    ●
    the
    action of the Commission or the staff, acting pursuant to delegated authority, in declaring the filing effective, does not relieve
    the Company from its full responsibility for the adequacy and accuracy of the disclosure in the filing; and

    ●
    the
    Company may not assert this action as a defense in any proceeding initiated by the Commission or any person under the federal securities
    laws of the United States.

    Very
    truly yours,

    PINEAPPLE
    FINANCIAL INC.

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
Dasgupta

    Title:
    Chief
    Executive Officer (Principal Executive Officer)

CORRESP
1
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EF
Hutton,

division
of Benchmark Investments, LLC

590
Madison Avenue, 39th Floor

New
York, NY 10022

July
6, 2023

VIA
EDGAR

United
States Securities and Exchange Commission

Division
of Corporation Finance

Office
of Trade & Services

100
F Street, N.E.

Washington,
D.C. 20549

Re:
Pineapple Financial Inc.

Registration
Statement on Form S-1

File
No. 333-268636

Ladies
and Gentlemen:

Pursuant
to Rule 461 under the Securities Act of 1933, as amended (the “Securities Act”), we, as representative of the underwriters
of the proposed public offering of securities of Pineapple Financial Inc. (the “Company”), hereby join the Company’s
request that the effective date of the above-referenced registration statement on Form S-1, as amended, be accelerated so that it will
be declared effective at 5:00 PM EDT on Thursday, July 6, 2023, or as soon thereafter as possible.

Pursuant
to Rule 460 under the Securities Act, we, as representative of the underwriters, wish to advise you that there will be distributed to
each underwriter, who is reasonably anticipated to participate in the distribution of the security, as many copies of the proposed form
of preliminary prospectus as appears to be reasonable to secure adequate distribution of the preliminary prospectus.

The
undersigned advises that it has complied and will continue to comply, and that it has been informed by the participating underwriters
and dealers that they have complied with and will continue to comply, with the requirements of Rule 15c2-8 under the Securities Exchange
Act of 1934, as amended.

    Very truly yours,

    EF HUTTON

    division of Benchmark Investments LLC

    By:
    /s/
    Sam Fleischman

    Name:
    Sam
Fleischman

    Title:
    Supervisory Principal

CORRESP
1
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  July 6,
  2023

VIA
EDGAR

Securities
and Exchange Commission

Division
of Corporation Finance

100
F Street N.E.

Washington,
D.C. 20549

    Re:
    Pineapple
    Financial, Inc

    Withdrawal
    of Acceleration Request - Registration Statement on Form S-1

    File
    No. 333-268636

Ladies
and Gentlemen:

Reference
is made to our letter, filed as correspondence via EDGAR on July 6, 2023, in which we requested the acceleration of the effective date
of the above-referenced Registration Statement for Thursday, July 6, 2023, at 5:00 p.m. EDT or as soon as reasonably practicable thereafter,
in accordance with Rule 461 under the Securities Act of 1933, as amended. We are no longer requesting that such Registration Statement
be declared effective at this time and we hereby formally withdraw such request for acceleration of the effective date.

    Very truly yours,

    PINEAPPLE FINANCIAL INC.

    By:
    /s/
    Shubha Dasgupta

    Name:
    Shubha
Dasgupta

    Title:
    Chief Executive Officer (Principal Executive Officer)

CORRESP
1
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EF
Hutton,

division
of Benchmark Investments, LLC

590
Madison Avenue, 39th Floor

New York, NY 10022

July
6, 2023

VIA
EDGAR

United
States Securities and Exchange Commission

Division of Corporation Finance

100
F. St., N.E.

Washington,
D.C. 20549

    Re:
    Pineapple
    Financial, Inc

    Withdrawal
    of Acceleration Request - Registration Statement on Form S-1

    File
    No. 333-268636

Ladies
and Gentlemen:

Reference
is made to our letter filed as correspondence via EDGAR on July 6, 2023, in which we requested the acceleration of the effective date
of the above-captioned Registration Statement for 5:00 PM EDT on Thursday, July 6, 2023 or as soon as reasonably practicable thereafter,
in accordance with Rule 461 of the Securities Act of 1933, as amended. We are no longer requesting that such Registration Statement be
declared effective at this time and we hereby formally withdraw our request for acceleration of the effective date.

    Very
    truly yours,

    EF
                                            HUTTON

    division
    of Benchmark Investments LLC

    By:
    /s/
    Sam Fleischman

    Name:
    Sam
Fleischman

    Title:
    Supervisory
    Principal

CORRESP
1
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PINEAPPLE
FINANCIAL INC.

Unit
200 111 Gordon Baker Road

Toronto,
Ontario M2H 3R1

Tel:
(416) 669-2046

July
5, 2023

VIA
EDGAR

Tonya
Aldave

Division
of Corporation Finance

Securities
and Exchange Commission

100
F Street, NE

Washington,
D.C. 20549

    Re:
    Re:
    Pineapple Financial Inc.

    Amendment
    No. 3 to Registration Statement on Form S-1

    Filed
    on June 21, 2023

    File
    No. 333-268636

Dear
Ms. Aldave,

On
behalf of Pineapple Financial Inc. (the “Company”), this letter responds to oral comments provided by the staff of the Division
of Corporation Finance (the “Staff”), of the Securities and Exchange Commission (the “Commission”), regarding
the Company’s Amendment No. 3 to the Registration Statement on Form S-1 (the “Registration Statement”) which was submitted
to the Commission on June 21, 2023.

Disclosure
changes made in response to the Staff’s oral comments have been made in an exhibit-only Amendment No. 4 to the Registration Statement
(“Amendment No. 4), which was filed with the Commission on July 5, 2023.

Registration
Statement on Form S-1

General

    In
    response to oral comments transmitted by telephone to the Darrin M. Ocasio, please be advised as follows:

    ●
    The
    opinion of Sichenzia Ross Ference LLP has been filed as Exhibit 5.2 in the Registration Statement, which provides, among other things,
    that the Representative’s Warrants will be valid and binding obligations of the Company enforceable against the Company in
    accordance with their terms under the laws of the State of New York.

We
thank the Staff for its review of the foregoing and the Registration Statement. If you have further comments, please feel free to contact
to our counsel, Darrin M. Ocasio., at dmocasio@srf.law or by telephone at (917) 848-6325 or Matthew Siracusa at msiracusa@srf.law,
telephone (845) 649-8868.

    Sincerely,

    /s/
    Shubha Dasgupta

    Shubha
    Dasgupta

CORRESP
1
filename1.htm

PINEAPPLE
FINANCIAL INC.

Unit
200 111 Gordon Baker Road

Toronto,
Ontario M2H 3R1

Tel:
(416) 669-2046

July
3, 2023

VIA
EDGAR

Susan
Block

Division
of Corporation Finance

Securities
and Exchange Commission

100
F Street, NE

Washington,
D.C. 20549

    Re:
    Re:
    Pineapple Financial Inc.

    Amendment
    No. 2 to Registration Statement on Form S-1

    Filed
    on May 16, 2023

    File
    No. 333-268636

Dear
Ms. Block,

On
behalf of Pineapple Financial Inc. (the “Company”), this letter responds to oral comments provided by the staff of the Division
of Corporation Finance (the “Staff”), of the Securities and Exchange Commission (the “Commission”), regarding
the Company’s Amendment No. 2 to the Registration Statement on Form S-1 (the “Registration Statement”) which was submitted
to the Commission on May 16, 2023.

Disclosure
changes made in response to the Staff’s oral comments have been made in an Amendment No. 3 to the Registration Statement (“Amendment
No. 3), which was filed with the Commission contemporaneously on June 21, 2023.

Registration
Statement on Form S-1

Business
– Incorporation, Page 47

    In response to oral comments transmitted by telephone to the Matthew Siracusa, please be advised as follows:

    ●
    The
    language under “Incorporation” on page 47 of Amendment No. 3 has been revised to be consistent with the Company’s
    amended articles, including the elimination of the references to Class A shares, Class B Shares, and Class C shares.

We
thank the Staff for its review of the foregoing and the Registration Statement. If you have further comments, please feel free to contact
to our counsel, Darrin M. Ocasio., at dmocasio@srf.law or by telephone at (917) 848-6325 or Matthew Siracusa at msiracusa@srf.law,
telephone (845) 649-8868.

    Sincerely,

    /s/
    Shubha Dasgupta

    Shubha
    Dasgupta

CORRESP
1
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PINEAPPLE
FINANCIAL INC.

Unit
200 111 Gordon Baker Road

Toronto,
Ontario M2H 3R1

Tel:
(416) 669-2046

January 4, 2023

VIA
EDGAR

Susan
Block

Division
of Corporation Finance

Securities
and Exchange Commission

100
F Street, NE

Washington,
D.C. 20549

    Re:
    Re:
    Pineapple Financial Inc.

    Registration
                                            Statement on Form S-1

    Filed on December 1, 2022

    File
    No. 333-268636

Dear
Ms. Block,

On
behalf of Pineapple Financial Inc. (the “Company”), this letter responds to comments provided by the staff of the Division
of Corporation Finance (the “Staff”), of the Securities and Exchange Commission (the “Commission”) provided to
the undersigned on December 13, 2022, regarding the Company’s Registration Statement on Form S-1 (the “Registration Statement”),
which was submitted to the Commission on December 1, 2022.

For
convenience, the Staff’s comments have been restated below and the Company’s responses are set out immediately under the
restated comments. An amendment to the Registration Statement on Form S-1 (“Amendment No. 1.”) reflecting changes made in
response to the Staff’s comments, along with changes made to update certain other information in the Registration Statement, has
also been submitted on this date. Unless otherwise indicated, defined terms used herein have the meanings set forth in the Registration
Statement.

Registration
Statement on Form S-1

General

1. It
                                            appears that you are conducting a firm commitment underwritten offering but on the cover
                                            page you checked the box that securities being registered are to be offered on a delayed
                                            or continuous basis pursuant to Rule 415. In addition, you have included some Rule 415 undertakings
                                            in Item 17 on page II-5. Please revise for consistency or advise.

Response:
The Company acknowledges the Staff’s comment and has unchecked the box that securities being registered are to be offered on a
delayed or continuous basis pursuant to Rule 415 on the cover page

We
look forward to working with you to have the Company approved for listing on the Nasdaq Stock Market. In connection there with, Shubha
Dasgupta, the Company’s Chief Executive Officer, would like the opportunity to address any concerns that you may have with the
Company’s application as soon as possible. Thank you very much for your cooperation.

If
you need any additional information or have any follow up questions, please feel free to contact me.

    Sincerely,

    /s/
Shubha
    Dasgupta

    Shubha
    Dasgupta

United States securities and exchange commission logo
December 13, 2022
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 on December 1, 2022
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.  Unless we note
otherwise, our references to prior comments are to comments in our October 26, 2022 letter.
Registration Statement on Form S-1
General
1.It appears that you are conducting a firm commitment underwritten offering but on the
cover page you checked the box that securities being registered are to be offered on a
delayed or continuous basis pursuant to Rule 415.  In addition, you have included some
Rule 415 undertakings in Item 17 on page II-5.  Please revise for consistency or advise.

 FirstName LastNameShubha Dasgupta
 Comapany NamePineapple Financial Inc.
 December 13, 2022 Page 2
 FirstName LastName
Shubha Dasgupta
Pineapple Financial Inc.
December 13, 2022
Page 2
            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,
Division of Corporation Finance
Office of Finance
cc:       Darrin Ocasio, Esq.

CORRESP
1
filename1.htm

PINEAPPLE
FINANCIAL INC.

Unit
200 111 Gordon Baker Road

Toronto,
Ontario M2H 3R1

Tel:
(416) 669-2046

 December
1,  2022

VIA
EDGAR

Susan
Block

Division
of Corporation Finance

Securities
and Exchange Commission

100
F Street, NE

Washington,
D.C. 20549

    Re:
    Pineapple Financial Inc.

    Amendment
    No. 1 to

    Draft
    Registration Statement on Form S-1

    Submitted
    on October 12, 2022

    CIK
    No. 0001938109

Dear
Ms. Block,

On
behalf of Pineapple Financial Inc. (the “Company”), this letter responds to comments provided by the staff of the Division
of Corporation Finance (the “Staff”), of the Securities and Exchange Commission (the “Commission”) provided to
the undersigned on October 26, 2022, regarding the Company’s Amendment No. 1 to Draft Registration Statement on Form S-1 (the “Draft
Registration Statement”), which was submitted to the Commission on October 12, 2022.

For
convenience, the Staff’s comments have been restated below and the Company’s responses are set out immediately under the
restated comments. A Registration Statement on Form S-1 (“Registration Statement”) reflecting changes made in response to
the Staff’s comments, along with changes made to update certain other information in the Draft Registration Statement, has also
been submitted on this date. Unless otherwise indicated, defined terms used herein have the meanings set forth in the Registration Statement.

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).

Response:
The Company acknowledges the Staff’s comment and has added additional disclosure in the Prospectus Summary under the heading “Equity
Structure” regarding our multiple class share structure.

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 business and
                                            macroeconomic conditions, such as economic 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.

Response:
The Company acknowledges the Staff’s comment and has revised such risk factor in the Registration Statement to address the
Staff’s comment.

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.

Response:
The Company acknowledges the Staff’s comment and has revised such risk factor in the Registration Statement to clarify where in
the cycle the Company believes interest rates are and how the rising interest rate environment is impacting the Company’s 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.

Response:
The Company acknowledges the Staff’s comment and has removed “including acquisitions” in the “Use of Proceeds”
section.

Management’s
Discussion and Analysis of Financial 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
                                            that in the business section on page 33 the total amount of agents is 627 — the same
                                            number as the total number of Users found on page 27 — which seems to include agents
                                            and consumers. As such, please revise throughout to consistently define “Users.”

Response:
The Company acknowledges the Staff’s comment and has clarified such disclosures in the Registration Statement to address the
Staff’s comment.

Business

Insurance
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.

Response:
The Company acknowledges the Staff’s comment and has provided the requested disclosures on page 38. In addition, the Company
has added an additional risk factor disclosure on page 10 in the Registration Statement.

 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 being
                                            presented by the mortgage broker channel must include the option for a client to consider
                                            certain insurance options.

Response:
The Company acknowledges the Staff’s comment and has included such explanation on page 36 in the Registration Statement.

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.

Response:
The Company acknowledges the Staff’s comment and has updated the Principal Shareholder table to provide ownership as of the most
recent practicable date.

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.”

Response:
The Company acknowledges the Staff’s comment and has revised the disclosure on page 61 in the Registration Statement.

We
look forward to working with you to have the Company approved for listing on the Nasdaq Stock Market. In connection there with, Shubha
Dasgupta, the Company’s Chief Executive Officer, would like the opportunity to address any concerns that you may have with the
Company’s application as soon as possible. Thank you very much for your cooperation.

If
you need any additional information or have any follow up questions, please feel free to contact me.

    Sincerely,

    /s/
    Shubha Dasgupta

    Shubha
    Dasgupta

United States securities and exchange commission logo
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

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 October 26, 2022 Page 2
 FirstName LastNameShubha Dasgupta
Pineapple Financial Inc.
October 26, 2022
Page 2
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

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

United States securities and exchange commission logo
September 28, 2022
Shubha Dasgupta
Chief Executive Officer
Pineapple Financial Inc.
Unit 200, 111 Gordon Baker Road
North York, Ontario M2H 3R1
Re:Pineapple Financial Inc.
Draft Registration Statement on Form S-1
Submitted on September 1, 2022
CIK No. 0001938109
Dear Mr. Dasgupta:
            We have reviewed your 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.
Draft Registration Statement on Form S-1
General
1.Please revise your cover page, summary, and risk factors sections to disclose your
multiple class share structure (Common Shares, Class A Shares, Class B Shares, and Class
C Shares) and explain the nature of the disparate voting rights and the risks the structure
presents to investors.
Prospectus Summary
Our Company, page 1
2.We note the statements that you are "dedicated to driving growth," through "innovative
data-driven systems," offer a "progressive" network that works "seamlessly."  We also

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 September 28, 2022 Page 2
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Shubha Dasgupta
Pineapple Financial Inc.
September 28, 2022
Page 2
note the statements that your Brokerage Services are "distinct and cutting-edge" and
MyPineapple was built to create long-term "competitive advantage relative to traditional
service providers."  Please substantiate those claims to us or revise to state those as your
beliefs.
3.In one of the opening paragraphs, please include your revenue and net losses for your
most recent audited period and interim stub to provide a financial snapshot of your
company, and to balance the disclosure in the summary.
Implications of Being an Emerging Growth Company, page 5
4.We note disclosure that as an emerging growth company you have elected to take
advantage of the extended transition period provided in Section 7(a)(2)(B) of the
Securities Act for complying with new or revised accounting standards. However, you
also disclose on the cover page of your filing that you have elected not to use the extended
transition period. Please revise your filing accordingly.
Risk Factors, page 8
5.Please revise your subheadings to adequately describe the risks, expanding upon the short
phrases you have currently, such as "Additional Funding" or "Limited Operating
History."  Succinctly state in your subheadings the risks that result from the facts or
uncertainties discussed in the risk factor.
6.Please add a separately captioned risk factor addressing the currency exchange rate
fluctuations and risks to investors.  In this regard we note your disclosure in the financial
statements that your functional currency is Canadian Dollars, but your presentation
currency is US Dollars.
Changes in Interest Rates, page 12
7.Please revise your discussion in the risk factor, as well as the subheading, to clarify where
in the cycle interest rates are and the effect on your business, so that investors may assess
the risk.
Repurchase Obligations and Breach of Representations, page 13
8.Please revise to briefly clarify what you mean by the statement that you "place the
mortgages that [you] originate."
We are subject to general economic conditions, page 13
9.Please update this risk factor if recent inflationary pressures have materially
impacted your operations. In this regard, identify the types of inflationary pressures you
are facing and how your business has been affected.

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Pineapple Financial Inc.
September 28, 2022
Page 3
Use of Proceeds, page 22
10.We note the different Use of Proceeds discussed.  Please disclose the approximate amount
intended to be used for each listed purpose.  If any material amounts of other funds are
needed to accomplish the specified purposes for which the proceeds are to be obtained,
state the amounts of such other funds needed and the sources thereof.  We also note that
funding potential mergers and acquisitions is discussed.  Please identify the businesses or
nature of businesses sought, the status of any negotiations, and a brief description of the
businesses.  Refer to Instruction 6 to Item 504 of Regulation S-K.
Management's Discussion and Analysis of Financial Condition and Results of Operations
Revenue Model, page 26
11.We note your disclosure on page 27 that you "have seen positive growth in all key
performance indicators including revenue, funded mortgage volume and EBITDA."
Please balance this disclosure by also quantifying your losses in the most recent fiscal
year and interim stub.  In addition, when you refer to "organic growth of the number of
Users engaged by the Company" here and the fact that your "active users increased at a
rate of approximately 85%" on page 38, please quantify the growth, disclose the number
of active users you currently have, and how you define active users.
Business, page 33
12.Please revise your business section to include a discussion of your services' distribution
methods, the fee structure for each business line, the number of field agents, and the
number of total and full-time employees. Refer to Item 101(h) of Regulation S-K.
Insurance Products, page 35
13.Please include risk factor disclosure regarding your insurance products, to the extent
applicable, including any risks related to developing this business.  In that regard, please
clarify here how far along in development you are with your insurance business, as we
note the discussion seems to indicate that Pineapple Insurance Inc. is to serve insurance
needs of your brand mortgage brokers and agents across Canada.  Please also discuss any
regulations related to the insurance aspect of your business.
InsurTech, page 36
14.We note your disclosure here that MyPineapple was built "in order to streamline and
manage the customer flow of insurance products" and that the "process is designed to
create a unique synchronicity between the client obtaining a mortgage approval and
insurance approval."  We also note your disclosure on pages 35-36 where you list the
insurance products you offer as the following: life insurance, accident and disability
insurance, critical illness insurance and credit insurance.  Please tell us if you offer any
other types of insurance.  If not, explain how the enumerated list of insurance products is

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September 28, 2022
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related to obtaining a mortgage.
Executive and Director Compensation
Summary Compensation Table, page 52
15.Consistent with your disclosure on pages 56 and F-27, please include in the summary
compensation table the 245,000 options granted to Mr. Shah in fiscal year 2021.
Certain Relationships and Related Party Transactions, page 57
16.We note your disclosure on page F-38 that you have entered into an arrangement with
Gravitas Securities Inc., a related party and shareholder.  Please disclose this transaction
here or tell us why it is not required to be disclosed.
Principal Shareholders, page 58
17.It appears based on your disclosure on page F-38 that Gravitas received a significant
number of shares for services provided in the 2021 Private Placement and should be
included as a beneficial shareholder in the table on page 58.  Please tell us what
percentage of your common shares Gravitas currently holds or has a right to
acquire within 60 days.  If that percentage is five percent or higher, include Gravitas'
holdings in the beneficial ownership table.  In addition, update the table to provide
ownership as of the most recent practicable date.
Description of Securities, page 59
18.Please include a section describing the rights of Common Shares.  In this regard, we note
that you only describe Class A, Class B and Class C shares here.  In addition, revise
the Dividends, Redemption, Dissolution, Purchase for Cancellation, Dissent and
Participation in Profits subsections to cover each of the four classes of shares.
19.We note your description of dividend rates to be paid to each class of common stock.
Please revise to clearly explain the following:
•list the order in which you will pay dividends to each of your shareholders,
•include sample calculations that will allow investors to understand what dividends
each type of common stock is entitled to, and
•clarify if any class of common stock is guaranteed to receive dividends.
Warrants, page 61
20.We note that you have two types of warrants, Compensation Warrants and Warrants.
Please include separate subheadings and describe characteristics of each type of warrant in
more detail.  In addition, you disclose that Common Shares are excisable into common
shares at a price ranging from $0.75-$1.87.  Please explain briefly how the exercise price
is calculated.

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Pineapple Financial Inc.
September 28, 2022
Page 5
Independent Auditor's Report, page F-3
21.Please revise to include the independent auditor's report.
Note 6. Share Capital, page F-17
22.We note your disclosure surrounding the 2021 private placement and that the allocation of
proceeds between common shares and warrants was made when the equity instruments
were issued using a relative fair value method.  Your disclosure on page F-31 appears to
indicate that you have allocated $6.1 million of the relative fair value to the common
shares and $1.4 million to the warrants as paid-in capital.  We further note that the
allocation of proceeds to warrants will typically create a discount in the associated equity
instrument, which should be recognized as interest expense or as a dividend in some
cases.  Please tell us, and revise your filing to disclose, whether there is any such discount
associated with this transaction and if so, how it is accounted for in your financial
statements.  Refer to ASC 470-20-25-2.
23.Please tell us and revise your filing to explain what the $3.043 million of issuance costs
paid by issuance of warrants represents, how this amount was determined and accounted
for, and the authoritative accounting literature relied upon to support your conclusions.
Exhibits
24.Please file your affiliation agreemetns with certain licensed mortgage brokers, as
referenced on pages 1, 26 and 33, and describe their material terms or advise why you are
not required to file them.
            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,
Division of Corporation Finance
Office of Finance
cc:       Darrin Ocasio, Esq.