Pineapple Financial insider adds stake; total now 2.08M shares

Rhea-AI Filing Summary

Pineapple Financial Inc. (PAPL) Form 4 filing: Chief Operating Officer, Director and >10% owner Kendall Leo Marin disclosed open-market purchases on 23-24 June 2025.

• Shares acquired: 9,475 common shares across four purchases at prices ranging from $0.0490 to $0.0695.
• Post-transaction holding: 2,078,523 common shares held directly, in addition to 126,652 stock options and 25,651 warrants previously granted.
• Transaction code: “P” (open-market purchase), suggesting voluntary buying rather than option exercise.
• Relative size: The purchase increases Marin’s direct equity stake by roughly 0.46%, indicating incremental rather than transformative buying.
• Alignment of interests: Continued accumulation by a senior executive with significant existing ownership may be viewed as a confidence signal, especially at a depressed share price below ten cents.

No derivative transactions were reported in this filing. The option package referenced was granted on 3-Nov-2023 under the 2022 Omnibus Plan and is unaffected by the current purchases.

Positive

• Insider buying: COO/Director Kendall Leo Marin purchased 9,475 shares on the open market, indicating continued confidence in PAPL.
• High ownership alignment: Executive now holds 2.08 million shares, plus options and warrants, aligning interests with shareholders.

Negative

• Immaterial size: The additional shares increase the insider’s stake by less than 1%, offering limited informational value.
• Low acquisition price: Purchases below $0.07 highlight the stock’s depressed valuation and potential underlying challenges.

Insights

Financial Analyst

TL;DR: Insider bought 9.5k shares; positive sentiment but immaterial size.

Marin’s incremental purchase at $0.05-$0.07 signals personal conviction during a period of evident share-price weakness. However, the 9,475-share addition represents less than 1% of his 2.08 million-share stake and an even smaller fraction of outstanding shares, limiting market impact. The filing nonetheless confirms that the executive remains an active buyer rather than a seller, which investors often interpret favorably. With no accompanying derivative activity or corporate events, the disclosure is best viewed as a modest positive sentiment indicator rather than a catalyst.

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)
06/23/2025

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	06/23/2025		P		3,000	A	$0.0695	2,072,048(1)	D
Common Shares	06/23/2025		P		3,750	A	$0.0502	2,075,798(1)	D
Common Shares	06/23/2025		P		2,000	A	$0.0657	2,077,798(1)	D
Common Shares	06/24/2025		P		725	A	$0.049	2,078,523(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	06/25/2025
	** 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 the insider buy?

Kendall Leo Marin acquired 9,475 common shares on 23-24 June 2025.

At what price were the Pineapple Financial shares purchased?

Purchase prices ranged from $0.0490 to $0.0695 per share.

What is the insider’s total shareholding after the transactions?

Marin now owns 2,078,523 common shares directly, plus options and warrants.

Did the filing report any option exercises or derivative trades?

No—Table II shows no derivative transactions in this Form 4.

Why is Form 4 important for PAPL investors?

Form 4 reveals real-time insider trading activity, often used to gauge management’s confidence in the company.