Sec Form 3 Filing - Dasgupta Shubha-Jeet @ Pineapple Financial Inc. - 2023-10-12

FORM 3 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Dasgupta Shubha-Jeet 2. Issuer Name and Ticker or Trading Symbol Pineapple Financial Inc. [ PAPL] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director X __ 10% Owner X __ Officer (give title below) _____ Other (specify below) CEO (Last) (First) (Middle) 200-111 GORDON BAKER RD. 3. Date of Earliest Transaction (MM/DD/YY) 10/12/2023 (Street) TORONTO, A6M2H 3R1 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Share 846,154 ( 1 ) I 5032771 Ontario Inc. ( 2 )

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Stock Options ( 1 ) $ 3.6 ( 1 ) 06/14/2026 Common Shares 126,652 I 5032771 Ontario Inc. ( 2 ) Warrants $ 2.93 11/03/2023 11/02/2025 Common Shares 25,641 I 5032771 Ontario Inc.

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Dasgupta Shubha-Jeet 200-111 GORDON BAKER RD. TORONTO, A6M2H 3R1 X X CEO Signatures /s/ Shubha Dasgupta 07/29/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The stock options were issued to the Reporting Person, pursuant to 2022 Omnibus Equity Incentive Compensation Plan on November 03, 2023, the options are exercisable at $3.60 per share and vest over 2 years whereby 25% of the options granted vested on the date of grant, and the remaining unvested options vest in equal installments every 6 months thereafter. ( 2 )The shares beneficially owned by 5032771 Ontario Inc., an entity controlled by the Reporting Person.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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