DSNY CEO adds shares via ESPP; 100,000 options remain exercisable

Rhea-AI Filing Summary

Fred Vandenberg, CEO and director of Destiny Media Technologies, Inc. (DSNY), filed a Form 5 reporting annual changes in beneficial ownership for the fiscal year ended 08/31/2025. The filing shows two non-derivative purchases: 6,900 common shares acquired under an Employee Stock Purchase Plan at $0.52 (converted from C$0.72) and 7,500 purchased on 08/31/2025 at $0.29. Total reported common shares beneficially owned at year-end were 451,984. The filing also lists 100,000 stock options fully exercisable as of year-end, with 80,000 expiring on 11/01/2026 at $1.50 and 20,000 expiring on 07/25/2028 at $0.85.

Positive

• Insider accumulation: CEO purchased 6,900 shares via ESPP at $0.52
• Open‑market buy: CEO purchased 7,500 shares at $0.29
• Substantial direct stake: End-of-year beneficial ownership of 451,984 common shares

Negative

• Potential dilution: 100,000 exercisable stock options could increase share count if exercised
• Option exercise prices above some transaction prices: options at $1.50 and $0.85 exceed recent purchase prices of $0.52 and $0.29

Insights

Corporate Governance Analyst

Insider increased direct holdings and retains significant option-based upside.

The reporting shows the CEO and director holds 451,984 common shares and 100,000 stock options that were fully exercisable as of 08/31/2025. The purchases include an Employee Stock Purchase Plan buy and an open-market acquisition, indicating continued insider participation in equity ownership.

Retention of options with exercise prices of $1.50 and $0.85 presents potential dilution if exercises occur; expiration dates are 11/01/2026 and 07/25/2028. Monitor option exercise timing relative to market price over the next 12–36 months for potential dilution effects.

Equity Transactions Specialist

Recent small purchases signal incremental insider accumulation at sub-dollar prices.

The reported non-derivative buys were 6,900 shares via an ESPP at $0.52 (CAD conversion noted) and 7,500 shares in an open-market purchase at $0.29. These are modest in size but increase direct beneficial ownership to 451,984 shares.

Because the transaction sizes are small, near-term market impact is likely limited; however, the combination of open-market buys plus exercisable options creates a concrete cap on potential share count changes before the listed expiration dates in 2026 and 2028.

SEC Form 5

FORM 5

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

ANNUAL 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:			3235-0362
Estimated average burden
hours per response:			1.0

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

Form 3 Holdings Reported.

Form 4 Transactions Reported.

1. Name and Address of Reporting Person^*

Vandenberg Fred

(Last) (First) (Middle)

# 428 - 1575 W GEORGIA STREET

(Street)

VANCOUVER A1 V6G 2V3

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
DESTINY MEDIA TECHNOLOGIES INC [ DSNY ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

3. Statement for Issuer's Fiscal Year Ended (Month/Day/Year)
08/31/2025

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 at end of Issuer's Fiscal Year (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
				Amount	(A) or (D)	Price
Common Shares	08/29/2025	08/29/2025	A(1)	6,900	A	$0.52(2)	444,484	D
Common Shares	08/31/2025	08/31/2025	L(3)	7,500	A	$0.29	451,984	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)
					(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
STOCK OPTION (RIGHT TO BUY)	(5)						(5)	(5)	See footnote(5)	(5)		100,000(4)	D

Explanation of Responses:

1. Purchased under Employee Stock Purchase Plan, which transaction is exempt under Rule 16b-3(c) of the Securities Exchange Act of 1934.

2. The price reported in Column 4 was converted from the Canadian weighted average price of C $0.72 to USD using an exchange rate of CAD $1.3823=USD $1.00.

3. Open market or private purchase, small acquisition under Rule 16a-6

4. This balance represents previously reported transactions.

5. 80,000 stock options (right to buy common stock) are expiring on November 1, 2026 with exercise price of $1.50, 20,000 stock options (right to buy common stock) are expiring on July 25, 2028 with exercise price of $0.85. All stock options were fully exercisable as at August 31, 2025.

	/s/Fred Vandenberg	10/08/2025
	** 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.
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FAQ

What did DSNY insider Fred Vandenberg purchase in fiscal 2025?

He acquired 6,900 shares under an Employee Stock Purchase Plan at $0.52 and 7,500 shares in an open-market purchase at $0.29.

How many DSNY shares does the CEO beneficially own?

The filing reports beneficial ownership of 451,984 common shares as of the fiscal year end 08/31/2025.

How many stock options does the reporting person hold for DSNY?

He holds 100,000 exercisable stock options: 80,000 expire on 11/01/2026 at $1.50 and 20,000 expire on 07/25/2028 at $0.85.

Were any transactions exempt or converted from CAD?

Yes. The 6,900 share ESPP purchase was exempt under Rule 16b-3(c) and its price was converted from C$0.72 to $0.52 using CAD $1.3823=USD $1.00.

When was the Form 5 signed?

The Form 5 was signed by Fred Vandenberg on 10/08/2025.