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Stewart Scott Matthew

Disclosed activity across 2 companies

Tapewire entity
37996
SEC CIK
0001825415

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
ContextLogic Holdings Inc.LOGC · Entity 5343CFO & COOJune 12, 2026June 15, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

ContextLogic Holdings Inc.

Report date June 12, 2026 · Filed June 15, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common Stock, par value $0.0001 per shareSEC Table I · non-derivativeDirect60,000 Reported balance After 2026-06-12 transaction · row 1
1 source row

Row 1 · 2026-06-12 · Purchase · Acquired 10,000 · Balance 60,000

F1: The price reported in Column 4 is a weighted average price. These shares were bought in multiple transactions at prices ranging from $9.70 to $9.78, inclusive. The Reporting Person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares bought at each separate price within the ranges set forth above.

Filing footnotes · ownership attribution and instrument terms

F1: The price reported in Column 4 is a weighted average price. These shares were bought in multiple transactions at prices ranging from $9.70 to $9.78, inclusive. The Reporting Person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares bought at each separate price within the ranges set forth above.

Past disclosures · reporting ended (1)

No longer tracked through insider filings. These historical balances do not imply present ownership or a zero position.

CANTALOUPE, INC.

Report date May 08, 2026 · Filed May 08, 2026

Section 16 reporting ended · disclosed 2026-05-08. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect0 Reported balance After 2026-05-08 transaction · row 1 Sequence does not reconcile; account continuity is unresolved.
1 source row

Row 1 · 2026-05-08 · Disposition to issuer · Disposed 3,323 · Balance 0

F1: 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.

F2: 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").

Common StockSEC Table I · non-derivativeDirect0 Reported balance After 2026-05-08 transaction · row 2 Sequence does not reconcile; account continuity is unresolved.
1 source row

Row 2 · 2026-05-08 · Disposition to issuer · Disposed 23,254 · Balance 0

F3: 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.

Common StockSEC Table I · non-derivativeDirect0 Reported balance After 2026-05-08 transaction · row 3 Sequence does not reconcile; account continuity is unresolved.
1 source row

Row 3 · 2026-05-08 · Disposition to issuer · Disposed 50,000 · Balance 0

F4: 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

Non-Qualified Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $6.35 · Expires 2029-08-11Direct0 Reported balance After 2026-05-08 transaction · row 4 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 4 · 2026-05-08 · Disposition to issuer · Disposed 225,000 · Balance 0

F5: 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.

Non-Qualified Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $8.02 · Expires 2029-02-07Direct0 Reported balance After 2026-05-08 transaction · row 5 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 5 · 2026-05-08 · Disposition to issuer · Disposed 175,000 · Balance 0

F5: 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.

Non-Qualified Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $8.58 · Expires 2027-09-17Direct0 Reported balance After 2026-05-08 transaction · row 6 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 6 · 2026-05-08 · Disposition to issuer · Disposed 125,000 · Balance 0

F5: 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.

Non-Qualified Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $11.20 · Expires 2028-11-08Direct0 Reported balance After 2026-05-08 transaction · row 7 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 7 · 2026-05-08 · Disposition to issuer · Disposed 100,000 · Balance 0

F5: 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.

Filing footnotes · ownership attribution and instrument terms

F1: 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.

F2: 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").

F3: 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.

F4: 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

F5: 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.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
June 12, 2026 Filed Jun 15, 2026 21:40 UTC ContextLogic Holdings Inc. LOGC · Entity 5343 PurchaseCommon Stock, par value $0.0001 per share 10,000 $9.76 $97,600.00
Disclosure

SEC source: 0001825415-26-000009 · ownership.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · CFO & COO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 60,000

F1 · price: The price reported in Column 4 is a weighted average price. These shares were bought in multiple transactions at prices ranging from $9.70 to $9.78, inclusive. The Reporting Person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares bought at each separate price within the ranges set forth above.

Read SEC document
June 01, 2026 Filed Jun 3, 2026 17:05 UTC ContextLogic Holdings Inc. LOGC · Entity 5343 GrantRestricted Stock Units · Derivative 50,000 $0.00 Strike: $0.00 $0.00
Disclosure

SEC source: 0001825415-26-000006 · ownership.xml · derivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · CFO & COO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 50,000

Underlying: Common Stock · 50,000 shares

Expires not disclosed

F1 · kind: The Reporting Person was granted restricted stock units ("RSUs") which represent a contingent right to receive one share of the Issuer's Common Stock, $0.0001 par value, for each RSU.

F2 · derivative.exercise_date: Subject to the Reporting Person's continued service, the RSU's will vest in equal installments of 20% of the total RSUs subject to the award on each of the first through fifth anniversaries of the effective date. Vested RSUs will settle on or following the vesting date, but in any event, within 60 days following the vesting date (unless the Reporting Person and the Issuer have agreed in writing to a later settlement date pursuant to procedures the Issuer may prescribe at its discretion).

F2 · derivative.expiration_date: Subject to the Reporting Person's continued service, the RSU's will vest in equal installments of 20% of the total RSUs subject to the award on each of the first through fifth anniversaries of the effective date. Vested RSUs will settle on or following the vesting date, but in any event, within 60 days following the vesting date (unless the Reporting Person and the Issuer have agreed in writing to a later settlement date pursuant to procedures the Issuer may prescribe at its discretion).

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May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerNon-Qualified Stock Option (Right to Buy) · Derivative 100,000 Not disclosed Strike: $11.20 Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · derivative · entry 7

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 100,000 shares

Expires 2028-11-08

F5 · price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

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May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerNon-Qualified Stock Option (Right to Buy) · Derivative 125,000 Not disclosed Strike: $8.58 Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · derivative · entry 6

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 125,000 shares

Expires 2027-09-17

F5 · price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

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May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerNon-Qualified Stock Option (Right to Buy) · Derivative 175,000 Not disclosed Strike: $8.02 Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · derivative · entry 5

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 175,000 shares

Expires 2029-02-07

F5 · price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

Read SEC document
May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerNon-Qualified Stock Option (Right to Buy) · Derivative 225,000 Not disclosed Strike: $6.35 Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · derivative · entry 4

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 225,000 shares

Expires 2029-08-11

F5 · price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

Read SEC document
May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerCommon Stock 50,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · nonDerivative · entry 3

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F4 · price: 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

Read SEC document
May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerCommon Stock 23,254 Not disclosed Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · nonDerivative · entry 2

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F3 · price: 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.

Read SEC document
May 08, 2026 Filed May 8, 2026 20:27 UTC CANTALOUPE, INC. CTLP · Entity 45433 Disposition to issuerCommon Stock 3,323 Not disclosed Not disclosed
Disclosure

SEC source: 0001825415-26-000002 · wk-form4_1778272071.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F1 · price: 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.

F2 · price: 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").

Read SEC document
September 18, 2025 Filed Nov 20, 2025 13:00 UTC CANTALOUPE, INC. CTLP · Entity 45433 SaleCommon Stock 62,830 $10.63 $667,882.90
Disclosure

SEC source: 0001628280-25-053325 · wk-form4_1763643600.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 53,009

Read SEC document
August 01, 2025 Filed Aug 5, 2025 20:55 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 12,500 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-037903 · wk-form4_1754427344.xml · nonDerivative · entry 2

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 115,839

F2 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted based on the achievement of certain performance conditions described in the Notice of Restricted Stock Unit Grant under the 2018 Equity Incentive Plan and approved by the Company's Compensation Committee and immediately vest.

Read SEC document
August 01, 2025 Filed Aug 5, 2025 20:55 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 8,095 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-037903 · wk-form4_1754427344.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,339

F1 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted under the Company's long-term stock incentive plans ("LTIP's) and vests on a prorated basis based on the total number of shares of common stock subject to the the award multiplied by a fraction equal to the number of calendar days elapsed since the grant date of such award divided by 1095, subject to Reporting Person's continued service (as defined in the 2025 Merger Agreement) through each such vesting date.

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September 20, 2024 Filed Feb 25, 2025 21:39 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 14,264 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-007756 · wk-form4_1740519560.xml · nonDerivative · entry 3

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 95,244

F1 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted under the Company's long-term stock incentive plans ("LTIP's) and vests in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Reporting Person's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

Read SEC document
August 02, 2024 Filed Feb 25, 2025 21:39 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 37,500 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-007756 · wk-form4_1740519560.xml · nonDerivative · entry 2

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,980

F2 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was approved by the Company's Compensation Committee and vests in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Reporting Person's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

Read SEC document
August 04, 2023 Filed Feb 25, 2025 21:39 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 16,952 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-007756 · wk-form4_1740519560.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 43,480

F1 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted under the Company's long-term stock incentive plans ("LTIP's) and vests in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Reporting Person's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

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December 19, 2022 Filed Dec 19, 2022 23:40 UTC CANTALOUPE, INC. CTLP · Entity 45433 PurchaseCommon Stock 2,500 $4.00 $10,000.00
Disclosure

SEC source: 0001628280-22-032239 · wf-form4_167149320630731.xml · nonDerivative · entry 2

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 26,528

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December 15, 2022 Filed Dec 19, 2022 23:40 UTC CANTALOUPE, INC. CTLP · Entity 45433 PurchaseCommon Stock 7,500 $4.00 $30,000.00
Disclosure

SEC source: 0001628280-22-032239 · wf-form4_167149320630731.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 24,028

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August 12, 2022 Filed Aug 16, 2022 21:24 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantNon-Qualified Stock Option (Right to Buy) · Derivative 225,000 $0.00 Strike: $6.35 $0.00
Disclosure

SEC source: 0001628280-22-023036 · wf-form4_166068507459133.xml · derivative · entry 2

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,000

Underlying: Common Stock · 225,000 shares

Expires 2029-08-11

F2 · derivative.exercise_date: The options shall vest in three equal installments on each of the first three anniversaries of the Date of Grant, subject to the Reporting Person's continued service (as defined in Cantaloupe, Inc's Equity Incentive Plans) through each such vesting date.

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August 12, 2022 Filed Aug 16, 2022 21:24 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 11,260 $0.00 $0.00
Disclosure

SEC source: 0001628280-22-023036 · wf-form4_166068507459133.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,528

F1 · shares: Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted under the Company's long-term stock incentive plans ("LTIP's) and vests in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Reporting Person's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

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February 07, 2022 Filed Feb 9, 2022 21:07 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantNon-Qualified Stock Option (Right to Buy) · Derivative 175,000 $0.00 Strike: $8.02 $0.00
Disclosure

SEC source: 0001628280-22-002103 · wf-form4_164444084791762.xml · derivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 175,000

Underlying: Common Stock · 175,000 shares

Expires 2029-02-07

F1 · derivative.exercise_date: The stock options are eligible to vest as follows:(i) 117,000 stock options are eligible to vest in three equal annual installments on the first three anniversaries of February 1, 2022 and (ii) the remaining 58,000 stock options are eligible to vest in three equal annual installments on the first three anniversaries of February 1, 2022, subject, in each case, to the reporting person's continued employment, and, in the case of (ii), subject to the achievement of applicable performance goals during the respective fiscal year. The Compensation Committee established the performance goals as a price target for the trading price of the Company's common stock in each applicable fiscal year. The price target is achieved if the average closing price of the common stock during any consecutive 30-trading-day period during the applicable fiscal year meets or exceeds (a) $13.50 in the case of fiscal year 2022 (b) $16.50 in the case of fiscal year 2023 and (c) $19.50 in the case of fiscal year 2024.

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November 08, 2021 Filed Nov 10, 2021 22:55 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantNon-Qualified Stock Option (Right to Buy) · Derivative 100,000 $0.00 Strike: $11.20 $0.00
Disclosure

SEC source: 0001628280-21-022901 · wf-form4_163658491402806.xml · derivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 100,000

Underlying: Common Stock · 100,000 shares

Expires 2028-11-08

F1 · derivative.exercise_date: The options shall vest in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Mr. Stewart's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

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August 06, 2021 Filed Aug 25, 2021 01:37 UTC CANTALOUPE, INC. CTLP · Entity 45433 GrantCommon Stock 5,268 $0.00 $0.00
Disclosure

SEC source: 0001628280-21-017564 · wf-form4_162985540625098.xml · nonDerivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,268

F1 · shares: Represents Restricted Stock Units, each of which represent a nontransferable right to receive one share of the Issuer's common stock. The award was granted under the Company's long-term stock incentive plans and vests in three equal installments on each of the first three anniversaries of the Date of Grant, subject to Reporting Person's continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan) through each such vesting date.

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September 17, 2020 Filed Sep 22, 2020 23:18 UTC CANTALOUPE, INC. USAT · Entity 45433 GrantNon-Qualified Stock Option (Right to Buy) · Derivative 125,000 $0.00 Strike: $8.58 $0.00
Disclosure

SEC source: 0001567619-20-017009 · doc1.xml · derivative · entry 1

Stewart Scott Matthew · CIK 0001825415 · Chief Accounting Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 125,000

Underlying: Common Stock · 125,000 shares

Expires 2027-09-17

F1 · derivative.exercise_date: The stock options are eligible to vest as follows: (i) 50% of the options are eligible to vest in 3 equal annual installments on the first 3 anniversaries of September 15, 2020, and (ii) the remaining 50% of the options are eligible to vest in 3 equal installments on each of the first 3 anniversaries of September 15, 2020, subject to the achievement of certain performance goals, and in each case subject to Mr. Stewart's continued employment through the applicable vesting date.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.