Gaurav Singal - 18 Sep 2025 Form 4 Insider Report for CANTALOUPE, INC. (CTLP)

Role: Chief Technology Officer
Signature: /s/ Anna Novoseletsky, Attorney in Fact
Issuer symbol: CTLP
Transactions as of: 18 Sep 2025
Net transactions value: -$2,126,000
Form type: 4
Filing time: 19 Sep 2025, 16:41:42 UTC
Previous filing: 05 Aug 2025
Next filing: 24 Sep 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Singal Gaurav	Chief Technology Officer	101 LINDENWOOD DRIVE, SUITE 405, MALVERN	/s/ Anna Novoseletsky, Attorney in Fact	19 Sep 2025	0001978412

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CTLP	Common Stock	Options Exercise	$654,000	+200,000	+493%	$3.27	240,533	18 Sep 2025	Direct	F1
transaction	CTLP	Common Stock	Sale	$2,126,000	-200,000	-83%	$10.63	40,533	18 Sep 2025	Direct	F1

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	CTLP	Non-Qualified Stock Option (Right to Buy)	Options Exercise	$654,000	-200,000	-100%	$3.27	0	18 Sep 2025	Non-Qualified Stock Option (Right to Buy)	200,000	$3.27	Direct	F1

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.

Content

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.