Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 28

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 28
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 of certain other regulatory authorities. The parties have agreed to use their reasonable best efforts to make the required regulatory filings as promptly as practicable, subject to cooperation between the parties pursuant to the Merger Agreement.

For further discussion of regulatory matters relating to the Merger, see the section of this proxy statement titled “ The Merger Agreement—Consents, Approvals and Filings ”.

#### Redemption of Preferred Stock (Page85)
Five business days prior to the date of the closing of the Merger (or such other date as Cantaloupe and 365 agree), Cantaloupe will send, in accordance with the Cantaloupe Articles and applicable law, written notice (which we refer to as the “Redemption Notice”), reasonably acceptable to 365, of the Redemption to each record holder of such shares of preferred stock.

Immediately prior to the effective time of the Merger, Cantaloupe will effect the Redemption. 365 has agreed to provide (or to cause to be provided) immediately available funds to Cantaloupe to pay the full amount to each former holder of preferred stock to which such former holder is entitled pursuant to the Cantaloupe Articles in connection with the Redemption.

See the section of this proxy statement titled “ The Merger Agreement—Redemption of Preferred Stock ”.

#### Fees and Expenses (Page89)
All fees and expenses incurred in connection with the Merger Agreement, the Merger and the other transactions contemplated by the Merger Agreement will be paid by the party incurring such fees or expenses, whether or not the Merger or any of the other transactions contemplated by the Merger Agreement are completed, with certain exceptions expressly set forth in the Merger Agreement. These exceptions include reimbursement by 365 of reasonable out-of-pocket expenses incurred by Cantaloupe or its subsidiaries in connection with Cantaloupe’s or its subsidiaries’ cooperation in connection with 365’s arrangement of the Debt Financing.

For more information on fees and expenses incurred in connection with the Merger Agreement and the Merger, see the section of this proxy statement titled “ The Merger Agreement—Fees and Expenses ”.

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#### TABLE OF CONTENTS

#### Help in Answering Questions
We greatly appreciate your cooperation in voting your shares. If you have any questions about the Special Meeting or the Merger after reading this proxy statement, our shareholders may contact Sodali & Co. (which we refer to as “Sodali”), our proxy solicitor, by telephone at