[Form 4] Pineapple Financial Inc. Insider Trading Activity

Rhea-AI Filing Summary

Kendall Marin, COO and Director of Pineapple Financial (PAPL), significantly increased their direct ownership position through multiple share purchases over two days:

On June 25, 2025:

• 46,100 shares at $0.08
• 32,000 shares at $0.0629
• 1,500 shares at $0.062

On June 26, 2025:

• 38,000 shares at $0.09
• 1,500 shares at $0.085
• 15,000 shares at $0.0899
• 2,700 shares at $0.08
• 2,000 shares at $0.0798

Total direct ownership following transactions: 2,217,323 shares. Additionally holds 126,652 options ($3.60 strike, vesting over 2 years) and 25,651 warrants. As both COO and 10% owner, these insider purchases may signal management's confidence in the company's prospects.

Positive

• COO and 10% owner Kendall Marin made significant open market purchases totaling 138,800 shares worth approximately $11,000, demonstrating insider confidence in the company at prices between $0.062-$0.09 per share
• The insider's total holdings increased to 2,217,323 shares, maintaining a substantial position as a 10% owner, indicating long-term commitment to the company

Negative

• The stock's current trading price ($0.062-$0.09) represents a significant decline from the $3.60 option strike price from November 2023, indicating substantial share price deterioration

SEC Form 4

FORM 4

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
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Marin Kendall Leo

(Last) (First) (Middle)

1 COUNTRY CLUB CRECENT

(Street)

UXBRIDGE A6 L9P 0B8

(City) (State) (Zip)

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)
	COO

3. Date of Earliest Transaction (Month/Day/Year)
06/25/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	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 Shares	06/25/2025		P		46,100	A	$0.08	2,124,623(1)	D
Common Shares	06/25/2025		P		32,000	A	$0.0629	2,156,623(1)	D
Common Shares	06/25/2025		P		1,500	A	$0.062	2,158,123(1)	D
Common Shares	06/26/2025		P		38,000	A	$0.09	2,196,123(1)	D
Common Shares	06/26/2025		P		1,500	A	$0.085	2,197,623(1)	D
Common Shares	06/26/2025		P		15,000	A	$0.0899	2,212,623(1)	D
Common Shares	06/26/2025		P		2,700	A	$0.08	2,215,323(1)	D
Common Shares	06/26/2025		P		2,000	A	$0.0798	2,217,323(1)	D

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 (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	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 (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (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: 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

Explanation of Responses:

1. Total excludes the 126,652 options and 25,651 warrants owned by the Reporting Person. 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.

	/s/ Kendall Marin	06/27/2025
	** Signature of Reporting Person	Date
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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

How many PAPL shares did COO Kendall Marin purchase on June 25, 2025?

On June 25, 2025, COO Kendall Marin purchased a total of 79,600 PAPL shares across three transactions: 46,100 shares at $0.08, 32,000 shares at $0.0629, and 1,500 shares at $0.062 per share.

What is the total number of PAPL shares owned by Kendall Marin after all reported transactions?

After all reported transactions on June 25-26, 2025, Kendall Marin directly owned 2,217,323 common shares of PAPL. This total excludes 126,652 options and 25,651 warrants also owned by Marin.

What positions does Kendall Marin hold at PAPL?

Kendall Marin holds multiple positions at PAPL: Chief Operating Officer (COO), Director, and is also a 10% Owner of the company.

What are the terms of PAPL stock options owned by Kendall Marin?

Marin owns 126,652 stock options issued under the 2022 Omnibus Equity Incentive Compensation Plan on November 03, 2023. The options are exercisable at $3.60 per share and vest over 2 years, with 25% vested at grant and the remainder vesting in equal installments every 6 months.

What was the price range of PAPL shares purchased by Marin on June 26, 2025?

On June 26, 2025, Marin purchased PAPL shares at prices ranging from $0.0798 to $0.09 per share, with transactions at $0.09, $0.085, $0.0899, $0.08, and $0.0798.