Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 59

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 59
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 is not completed for any other reason, our shareholders will not receive the merger consideration or any payment for their shares of Cantaloupe stock in connection with the Merger. Instead, Cantaloupe will remain an independent public company and our common stock will continue to be listed and traded on the Nasdaq. In certain circumstances, we may be required to pay a termination fee in connection with a termination of the Merger Agreement. For more information about the circumstances in which Cantaloupe must pay 365 such termination fee, see the section of this proxy statement titled “ The Merger Agreement—Termination Fee; Effect of Termination ”. Additionally, if the Merger is not completed, Cantaloupe does not expect to redeem any shares of preferred stock.

### Background of the Merger
Cantaloupe’s Board and executive management team regularly review Cantaloupe’s independent strategic plans, and consider various strategic alternatives potentially available to Cantaloupe, all with the goal of enhancing value for

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#### TABLE OF CONTENTS
Cantaloupe and its shareholders. These reviews have included consideration, from time to time, of potential partnerships, collaborations and other strategic transactions to enhance shareholder value, including potential sale transactions, consistent with shareholder requests over time. Cantaloupe’s executive management and the Board also engage in discussions from time to time with various industry participants, including strategic parties and financial sponsors, as well as financing sources, market participants and investment banking firms, regarding Cantaloupe’s business, strategy and growth opportunities, including opportunities for collaboration, potential business combinations, divestitures, acquisitions and financing transactions, and Cantaloupe’s executive management regularly updates the Board regarding the occurrence of such discussions.

As part of these discussions, Ravi Venkatesan, Cantaloupe’s Chief Executive Officer, has engaged in ordinary course conversations from time to time with various industry participants, including strategic parties and financial sponsors. Such conversations included separate meetings with representatives of two financial acquirors (which we refer to as “Party A” and “Party B”) and a strategic acquiror (which we refer to as “Party C”), at which meetings Mr. Venkatesan and such representatives discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On December 4, 2024, representatives of a financial acquiror (which we refer to as “Party D”) contacted Mr. Ven