[Form 4] Pineapple Financial Inc. Insider Trading Activity

Rhea-AI Filing Summary

Pineapple Financial Inc. (PAPL) – Form 4 insider activity

COO, Director and 10% owner Kendall Leo Marin disclosed a series of open-market purchases between 27 June 2025 and 2 July 2025. Four transactions coded “P” (purchase) added a cumulative 55,500 common shares at a volume-weighted average price of roughly $0.096 per share (price range $0.085–$0.10). The cash outlay is approximately $5.3 thousand.

Following the trades, Marin directly owns 2,272,823 common shares, plus 126,652 stock options (exercisable at $3.60, vesting through 2025) and 25,651 warrants. No derivative securities were bought or sold in the current period.

The incremental purchase represents an estimated +2.5% increase to Marin’s prior common-share position, signalling continued confidence at prices far below the outstanding option strike. For micro-cap investors, repeat insider buying—especially by a multi-hat executive—can be interpreted as a favorable sentiment indicator, though the dollar value remains modest.

Positive

• Repeat insider buying by COO/Director/10% owner indicates management confidence.
• Ownership increase of 55,500 shares raises direct stake to over 2.27 million shares, enhancing alignment with shareholders.

Negative

• Purchases total only ~$5k, a small dollar commitment that may limit market impact.

Insights

Sell-side Financial Analyst

TL;DR – Executive adds 55.5k shares at ~$0.10; signals confidence but dollar size small.

The Form 4 shows steady accumulation by PAPL’s COO/Director. Although $5 k is immaterial in absolute terms, the trades lift his stake by ~2.5%. Given the deep discount to the $3.60 option strike, the purchases suggest management views current prices as undervalued. For a thinly traded micro-cap, any insider buying can tighten the public float and improve sentiment. I view the filing as a modestly positive data point, but not thesis-changing unless follow-on buying continues.

Corporate Governance Specialist

TL;DR – Routine insider buy, aligns interests; governance impact limited.

The transaction complies with Section 16 reporting rules and involves open-market purchases, avoiding related-party complexity. While additional ownership aligns incentives, the relative size versus existing holdings is minor. No derivative exercises or sales were disclosed, which removes potential conflict signals. Overall governance impact is neutral-to-positive; investors should watch for consistent buying patterns or larger dollar commitments.

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)
06/27/2025

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	06/27/2025		P		19,500	A	$0.095(1)	2,236,823(2)	D
Common Shares	06/30/2025		P		18,000	A	$0.094(1)	2,254,823(2)	D
Common Shares	07/01/2025		P		4,000	A	$0.1	2,258,823(2)	D
Common Shares	07/02/2025		P		14,000	A	$0.1	2,272,823(2)	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. The reported price is a weighted average price. These shares were purchased in multiple transactions ranging from $0.085 to $0.10, inclusive. The reporting person undertakes to provide Pineapple Financial Inc., any security holder of Pineapple Financial Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares bought at each separate price within the range set forth in this footnote to this Form 4.

2. 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	07/03/2025
	** 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 Kendall Leo Marin purchase in this Form 4?

The insider bought 55,500 common shares between 27 June and 2 July 2025.

What price did the PAPL insider pay for the shares?

Shares were bought at a $0.085–$0.10 range, with a weighted average of roughly $0.096.

What is Kendall Leo Marin’s total PAPL ownership after the transactions?

He directly owns 2,272,823 common shares, plus 126,652 options and 25,651 warrants.

Were any derivative securities exercised or sold in this filing?

No. Only common shares were purchased; no options or warrants were exercised or disposed.

Does the Form 4 indicate a Rule 10b5-1 trading plan?

The filing does not mark the Rule 10b5-1 checkbox, suggesting trades were not executed under a pre-arranged plan.