[Form 4] Pineapple Financial Inc. Insider Trading Activity

Rhea-AI Filing Summary

Pineapple Financial Inc. (PAPL) – Form 4 insider activity: Chief Operating Officer, director and 10% shareholder Kendall Leo Marin reported open-market purchases of 9,000 common shares on 3 & 7 July 2025 at prices of $0.094-$0.099 per share, spending roughly $860. Following these trades, Marin directly owns 2,281,823 shares, up about 0.4% from prior holdings. The filing also discloses—but excludes from the share count—126,652 stock options (exercise price $3.60, vesting over two years) and 25,651 warrants. While the dollar amount is small relative to Marin’s existing stake, insider buying by a C-suite executive and large holder can be viewed as a confidence signal, especially with the stock trading below $0.10.

Insights

Financial Analyst

TL;DR: Small insider purchase; positive sentiment signal but immaterial to valuation.

The COO’s 9,000-share buy expands his direct stake to 2.28 million shares. Although the outlay is negligible (<$1k) and increases ownership by only 0.4%, buying—rather than selling—by a 10% owner tends to reassure investors that management believes the current sub-$0.10 price is undervalued. No new options were issued; the option package disclosed (126,652 @ $3.60) remains far out-of-the-money, suggesting cash purchases are opportunistic rather than compensation-driven. From a valuation standpoint the trade is not impactful, but sentiment leans modestly positive.

Corporate Governance Expert

TL;DR: Routine Form 4; governance posture unchanged.

The filing meets Section 16 reporting requirements within one business day, indicating compliant disclosure practices. Marin’s role as director, officer and 10% holder concentrates influence but the incremental share purchase does not materially alter control dynamics. No red flags such as late filings or sales into weakness appear. Overall governance impact is neutral.

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)
07/07/2025

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	07/03/2025		P		1,000	A	$0.095	2,273,823(1)	D
Common Shares	07/03/2025		P		2,000	A	$0.099	2,275,823(1)	D
Common Shares	07/07/2025		P		6,000	A	$0.094	2,281,823(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	07/08/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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