STOCK TITAN

Cantaloupe (CTLP) director’s shares and options canceled for $11.20 cash

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Cantaloupe, Inc. director Anne M. Smalling disposed of her remaining equity through the company’s merger transaction. On the merger’s effective date, 19,157 and 78,319 shares of common stock reported in this Form 4 were canceled and converted into the right to receive $11.20 per share in cash.

In addition, a non-qualified stock option for 120,000 shares with a per-share exercise price of $6.49 was canceled in exchange for cash calculated as the excess of the $11.20 merger consideration over the exercise price, multiplied by 120,000 shares. Following these transactions, the filing shows no remaining common stock or options held by Smalling.

Positive

  • None.

Negative

  • None.

Insights

Director’s entire equity position was cashed out mechanically in the merger.

This filing shows Anne M. Smalling, a director of Cantaloupe, Inc., disposing of all reported shares and options as part of a completed merger. The consideration is purely cash-based at $11.20 per common share, with options paid based on a defined formula.

The transactions are classified as dispositions to the issuer, not open-market trades, and derivativeSummary shows no remaining options. This makes the activity largely mechanical and driven by the merger terms rather than an independent trading decision, so informational value for future performance is limited.

Insider Smalling Anne M.
Role null
Type Security Shares Price Value
Disposition Non-Qualified Stock Option (Right to Buy) 120,000 $0.00 --
Disposition Common Stock 78,319 $0.00 --
Disposition Common Stock 19,157 $0.00 --
Holdings After Transaction: Non-Qualified Stock Option (Right to Buy) — 0 shares (Direct, null); Common Stock — 0 shares (Direct, null)
Footnotes (1)
  1. This Form 4 reports securities disposed of under the Agreement and Plan of Merger, dated as of June 15, 2025 (the "Merger Agreement"), by and among Cantaloupe, Inc. (the "Company"), 365 Retail Markets, LLC, Catalyst Holdco I, Inc., Catalyst Holdco II, Inc. and Catalyst MergerSub Inc. ("Merger Subsidiary"), under which Merger Subsidiary was merged with and into the Company (the "Merger"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the "Effective Time"), each share of common stock of the Company ("Common Stock") reported in this row of this Form 4 was canceled and automatically converted into the right to receive $11.20 in cash, without interest (such amount per share, the "Merger Consideration"). Each of these restricted stock units of the Company ("RSU") represented a contingent right to receive one share of Common Stock. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each RSU that was outstanding immediately prior to the Effective Time was fully vested and free of restrictions and was canceled and converted into the right to receive an amount in cash equal to the Merger Consideration. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each outstanding option to purchase one share of Common Stock ("Option") having a per share exercise price less than the Merger Consideration ("In-the-Money Option") became fully vested and free of restrictions and was canceled in exchange for cash in an amount equal to (A) the total number of shares of Common Stock for which such In-the-Money Option was exercisable, multiplied by (B) the excess of the Merger Consideration over the per share exercise price of such In-the-Money Option, and each outstanding Company Option having a per share exercise price equal to or greater than the Merger Consideration was canceled without consideration.
Common shares canceled (block 1) 19,157 shares Common Stock canceled for $11.20 cash per share at merger effective time
Common shares canceled (block 2) 78,319 shares Common Stock canceled for $11.20 cash per share at merger effective time
Merger consideration per share $11.20 per share Cash paid for each share of Cantaloupe common stock canceled in merger
Option shares canceled 120,000 option shares Non-qualified stock option canceled and exchanged for cash under merger terms
Option exercise price $6.49 per share Per-share exercise price of canceled non-qualified stock option
Post-transaction common shares 0 shares Total common stock held after reported dispositions
Dispose transactions count 3 transactions Two common stock and one option disposition to issuer reported
Agreement and Plan of Merger regulatory
"This Form 4 reports securities disposed of under the Agreement and Plan of Merger, dated as of June 15, 2025..."
An Agreement and Plan of Merger is a formal document where two companies agree to combine into one, outlining how the process will happen. It’s like a step-by-step plan for merging, and it matters because it shows both sides have agreed on the details before the official transition takes place.
Merger Consideration financial
"was canceled and automatically converted into the right to receive $11.20 in cash... such amount per share, the "Merger Consideration"."
Merger consideration is the total payment a company or buyer offers to shareholders of a target company in exchange for combining the two businesses, and can include cash, shares in the surviving company, debt assumption, or a mix of these. Investors care because the form and amount affect the deal’s value, tax consequences, immediate cash received versus future ownership, and the risk and upside of holding new shares — similar to choosing between cash now or stock that could grow later.
Non-Qualified Stock Option (Right to Buy) financial
"security_title": "Non-Qualified Stock Option (Right to Buy)""
restricted stock units financial
"Each of these restricted stock units of the Company ("RSU") represented a contingent right to receive one share..."
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
In-the-Money Option financial
"each outstanding option... having a per share exercise price less than the Merger Consideration ("In-the-Money Option")..."
effective time of the Merger regulatory
"At the effective time of the Merger (the "Effective Time"), each share of common stock..."
The effective time of the merger is the exact moment when a planned combination of two companies legally takes effect, usually specified in the merger agreement and reflected by the formal filing or timestamp. For investors, it is the point when ownership, voting rights, financial reporting and control shift—like a light switch flipping that joins two rooms into one—so it determines when shares convert, who controls corporate decisions and which results appear in financial statements.
SEC Form 4
FORM 4UNITED 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
X
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*
Smalling Anne M.

(Last)(First)(Middle)
101 LINDENWOOD DRIVE

(Street)
MALVERN PENNSYLVANIA 19355

(City)(State)(Zip)

UNITED STATES

(Country)
2. Issuer Name and Ticker or Trading Symbol
CANTALOUPE, INC. [ CTLP ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/08/2026
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
Common Stock05/08/2026D78,319D(1)(2)0D
Common Stock05/08/2026D19,157D(3)0D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Non-Qualified Stock Option (Right to Buy)$6.4905/08/2026D120,000 (4)05/06/2027(4)Common Stock120,000(4)0D
Explanation of Responses:
1. This Form 4 reports securities disposed of under the Agreement and Plan of Merger, dated as of June 15, 2025 (the "Merger Agreement"), by and among Cantaloupe, Inc. (the "Company"), 365 Retail Markets, LLC, Catalyst Holdco I, Inc., Catalyst Holdco II, Inc. and Catalyst MergerSub Inc. ("Merger Subsidiary"), under which Merger Subsidiary was merged with and into the Company (the "Merger"), with the Company continuing as the surviving corporation in the Merger.
2. At the effective time of the Merger (the "Effective Time"), each share of common stock of the Company ("Common Stock") reported in this row of this Form 4 was canceled and automatically converted into the right to receive $11.20 in cash, without interest (such amount per share, the "Merger Consideration").
3. Each of these restricted stock units of the Company ("RSU") represented a contingent right to receive one share of Common Stock. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each RSU that was outstanding immediately prior to the Effective Time was fully vested and free of restrictions and was canceled and converted into the right to receive an amount in cash equal to the Merger Consideration.
4. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each outstanding option to purchase one share of Common Stock ("Option") having a per share exercise price less than the Merger Consideration ("In-the-Money Option") became fully vested and free of restrictions and was canceled in exchange for cash in an amount equal to (A) the total number of shares of Common Stock for which such In-the-Money Option was exercisable, multiplied by (B) the excess of the Merger Consideration over the per share exercise price of such In-the-Money Option, and each outstanding Company Option having a per share exercise price equal to or greater than the Merger Consideration was canceled without consideration.
Remarks:
/s/ Anna Novoseletsky, Attorney in Fact05/08/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)