[Form 4] CANTALOUPE, INC. Insider Trading Activity

Rhea-AI Filing Summary

Gaurav Singal, Chief Technology Officer of Cantaloupe, Inc. (CTLP), exercised and sold shares on 09/18/2025. He exercised 200,000 stock options with an exercise price of $3.27 per share, received the underlying common stock and immediately sold 200,000 shares at a weighted-average price of $10.63 per share. After these transactions he directly beneficially owns 40,533 shares. The exercised options were granted October 22, 2022 and vested in three equal annual installments beginning October 27, 2022. The filing states the purchase prices for the sale ranged from $10.6257 to $10.6325 and that the reporting person will provide details on request.

Positive

• Transparency: Filing discloses exercise and sale amounts, exercise price ($3.27), sale weighted-average price ($10.63) and price range ($10.6257–$10.6325).
• Vested compensation realized: Options granted in October 2022 and vested over scheduled anniversaries, indicating normal vesting and compensation settlement.

Negative

• Reduction in insider holding: The insider sold 200,000 shares and now holds 40,533 shares directly, decreasing his direct stake.
• No 10b5-1 indication: The form does not check a box indicating the sale was pursuant to a Rule 10b5-1 trading plan.

Insights

Securities Analyst

TL;DR: Insider exercised vested options and sold all resulting shares same day, leaving a modest remaining direct holding of 40,533 shares.

The filing documents a routine option exercise followed by immediate disposition of the shares, consistent with either cashing out vested compensation or following a pre-existing sell plan. The exercise price of $3.27 versus sale proceeds at a weighted-average of $10.63 produced a realized spread per share of roughly $7.36 before taxes and fees. The transaction reduces the insider’s direct stock holdings to 40,533 shares, and the derivative position reports 0 options remaining exercisable following the reported transactions. This is a single-person, non-rule 10b5-1 disclosure and appears operationally straightforward without additional corporate actions disclosed.

Corporate Governance Expert

TL;DR: The disclosure reflects a compensation-related exercise and sale; materiality is limited absent further context on holdings or planned sales.

The footnote confirms the options were part of an October 2022 grant that vested over three anniversaries and that the exercised shares were sold in multiple broker transactions at prices between $10.6257 and $10.6325. The reporting attorney signed the form on 09/19/2025. From a governance perspective, the filing provides requisite transparency on timing, amounts and prices. No additional governance issues, trading restrictions, or Rule 10b5-1 plan indication are stated in the filing.

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^*

Singal Gaurav

(Last) (First) (Middle)

101 LINDENWOOD DRIVE

SUITE 405

(Street)

MALVERN PA 19355

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
CANTALOUPE, INC. [ CTLP ]

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

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

3. Date of Earliest Transaction (Month/Day/Year)
09/18/2025

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 Stock	09/18/2025		M		200,000(1)	A	$3.27	240,533	D
Common Stock	09/18/2025		S		200,000(1)	D	$10.63	40,533	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
Non-Qualified Stock Option (Right to Buy)	$3.27	09/18/2025		M			200,000	(1)	10/27/2029	Non-Qualified Stock Option (Right to Buy)	200,000	$3.27	0	D

Explanation of Responses:

1. Represents the exercise of stock options issued October 22, 2022, which vested in three equal annual installments on the first three anniversaries of the October 27, 2022 and in each case subject to Mr. Singal's continued employment through the applicable vesting dates. Immediately following the exercise of the stock options, the resulting common stock were sold. The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions through a broker-dealer at prices ranging from $10.6257 to $10.6325. Gaurav Singal (the "Reporting Person") undertakes to provide Cantaloupe, Inc. (the "Issuer"), any security holder of the Issuer, or the staff of the SEC, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote.

Remarks:

	/s/ Anna Novoseletsky, Attorney in Fact	09/19/2025
	** 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

What did CTLP insider Gaurav Singal do on 09/18/2025?

He exercised 200,000 options at $3.27 per share and immediately sold 200,000 resulting shares at a weighted-average price of $10.63 per share.

How many CTLP shares does Mr. Singal own after the transactions?

Following the transactions he directly beneficially owns 40,533 shares.

When were the exercised options originally granted and how did they vest?

The options were issued on October 22, 2022 and vested in three equal annual installments beginning on the first anniversary of October 27, 2022, subject to continued employment.

At what prices were the sold shares transacted?

The filing reports a weighted-average sale price of $10.63 and a per-transaction price range of $10.6257 to $10.6325.

Does the Form 4 indicate the sale was under a Rule 10b5-1 plan?

No. The form does not indicate that the transaction was made pursuant to a Rule 10b5-1 written plan.