STOCK TITAN

Cantaloupe (CTLP) CRO cashes out shares and options in $11.20-per-share merger

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

Rhea-AI Filing Summary

Cantaloupe, Inc. Chief Revenue Officer Jeffrey Charles Dumbrell reported multiple equity transactions tied to the company’s merger with 365 Retail Markets. At the merger’s effective time, each share of Cantaloupe common stock was canceled and converted into the right to receive $11.20 in cash per share as merger consideration.

The filing shows dispositions of common stock back to the issuer, one open-market sale, and the contribution of 20,000 shares to Garage Topco LP by The Dumbrell Family Trust under a rollover agreement. Restricted stock units, performance stock units, and in-the-money stock options became fully vested and were canceled in exchange for cash, while options with exercise prices at or above $11.20 were canceled without payment.

Positive

  • None.

Negative

  • None.

Insights

CRO’s equity awards are cashed out or canceled in a cash merger.

The transactions reflect how Cantaloupe, Inc. handled insider equity during its merger with 365 Retail Markets. Common shares were converted into a cash right of $11.20 per share, standard for an all-cash acquisition structure.

Equity awards were treated systematically: RSUs and PSUs vested and converted into cash at the merger price, while in-the-money options were paid out based on the spread over $11.20. Out-of-the-money options were canceled with no payment, eliminating remaining option overhang for this insider.

Insider Dumbrell Jeffrey Charles
Role Chief Revenue Officer
Sold 23,254 shs ($0.00)
Type Security Shares Price Value
Disposition Non-Qualified Stock Option (Right to Buy) 225,000 $0.00 --
Disposition Non-Qualified Stock Option (Right to Buy) 296,668 $0.00 --
Disposition Common Stock 12,220 $0.00 --
Other Common Stock 20,000 $0.00 --
Sale Common Stock 23,254 $0.00 --
Disposition Common Stock 50,000 $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"). In connection with the Merger, The Dumbrell Family Trust entered into a Rollover Agreement, dated as of February 19, 2026, pursuant to which, among other things, immediately prior to the Effective Time, The Dumbrell Family Trust contributed 20,000 shares of Common Stock to Garage Topco LP in exchange for common units of Garage Topco LP. 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. Each of these restricted stock units of the Company ("PSU") represented a contingent right to receive one share of Common Stock, subject to satisfying additional performance conditions. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each PSU that was outstanding immediately prior to the Effective Time which remained subject to vesting based on achieving certain performance metrics became vested with respect to that number of shares of Common Stock based on deemed achievement of the performance metrics at target performance, and was canceled and converted into the right to receive, with respect to each such vested share of Common Stock underlying such PSU, 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.
Merger consideration per share $11.20 per share Cash paid for each Cantaloupe common share at merger
Issuer disposition of common stock 50,000 shares Common stock disposed to issuer by CRO on Form 4 date
Open-market sale of common stock 23,254 shares Non-derivative sale reported as transaction code S
Rollover shares to Garage Topco LP 20,000 shares Contributed by The Dumbrell Family Trust under rollover agreement
Canceled option grant 1 296,668 options at $8.11 Non-qualified stock options disposed to issuer, in-the-money vs $11.20
Canceled option grant 2 225,000 options at $6.68 Non-qualified stock options disposed to issuer, in-the-money vs $11.20
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.
restricted stock units financial
"Each of these restricted stock units of the Company ("RSU") represented a contingent right to receive one share of Common Stock."
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.
performance stock units financial
"Each of these restricted stock units of the Company ("PSU") represented a contingent right to receive one share of Common Stock, subject to satisfying additional performance conditions."
Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.
In-the-Money Option financial
"…each outstanding option… having a per share exercise price less than the Merger Consideration ("In-the-Money Option") became fully vested…"
Rollover Agreement regulatory
"The Dumbrell Family Trust entered into a Rollover Agreement, dated as of February 19, 2026…"
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*
Dumbrell Jeffrey Charles

(Last)(First)(Middle)
101 LINDENWOOD DRIVE
SUITE 405

(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)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Revenue Officer
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 Stock05/08/2026D12,220D(1)(2)0D
Common Stock05/08/2026J20,000D(1)(3)0D
Common Stock05/08/2026S23,254D(4)0D
Common Stock05/08/2026D50,000D(5)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)$6.6805/08/2026D225,000(6) (6)08/12/2029(6)Non-Qualified Stock Option (Right to Buy)225,000(6)0D
Non-Qualified Stock Option (Right to Buy)$8.1105/08/2026D296,668(6) (6)12/22/2028(6)Non-Qualified Stock Option (Right to Buy)296,668(6)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. In connection with the Merger, The Dumbrell Family Trust entered into a Rollover Agreement, dated as of February 19, 2026, pursuant to which, among other things, immediately prior to the Effective Time, The Dumbrell Family Trust contributed 20,000 shares of Common Stock to Garage Topco LP in exchange for common units of Garage Topco LP.
4. 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.
5. Each of these restricted stock units of the Company ("PSU") represented a contingent right to receive one share of Common Stock, subject to satisfying additional performance conditions. Pursuant to the Merger Agreement, at or immediately prior to the Effective Time, each PSU that was outstanding immediately prior to the Effective Time which remained subject to vesting based on achieving certain performance metrics became vested with respect to that number of shares of Common Stock based on deemed achievement of the performance metrics at target performance, and was canceled and converted into the right to receive, with respect to each such vested share of Common Stock underlying such PSU, an amount in cash equal to the Merger Consideration
6. 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)

FAQ

What insider transactions did Cantaloupe (CTLP) CRO Jeffrey Dumbrell report?

He reported dispositions of common stock back to the issuer, one open-market sale, and changes to derivative awards. These occurred in connection with Cantaloupe’s cash merger, which converted equity holdings into cash or canceled them under agreed terms.

How were Cantaloupe (CTLP) common shares treated in the merger?

Each Cantaloupe common share was canceled and automatically converted into the right to receive $11.20 in cash, without interest. This fixed cash amount, called the merger consideration, applied to shares outstanding at the effective time of the merger transaction.

What happened to Jeffrey Dumbrell’s Cantaloupe (CTLP) stock options in the merger?

In-the-money options became fully vested and were canceled for cash equal to shares times the $11.20 merger price minus the exercise price. Options with exercise prices at or above the merger consideration were canceled without any payment to the holder.

How were Cantaloupe (CTLP) RSUs and PSUs handled under the merger agreement?

Each RSU vested and was canceled in exchange for cash equal to the $11.20 merger price per underlying share. PSUs vested at target performance, then were canceled for cash at the same per-share merger consideration, simplifying outstanding performance-based awards.

What role did The Dumbrell Family Trust play in the Cantaloupe (CTLP) merger?

The Dumbrell Family Trust entered a rollover agreement and contributed 20,000 Cantaloupe shares to Garage Topco LP immediately before the merger’s effective time. In return, the trust received common units of Garage Topco LP instead of taking the cash merger consideration for those shares.