Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 59

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 59
---
ger 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 Cantaloupe and its shareholders. These reviews have included consideration, from time to time, of potential

<div align='center'>29</div>

#### TABLE OF CONTENTS
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. Venkatesan via email to request a telephonic meeting. Mr. Venkatesan and representatives of Party D met telephonically on December 10, 2024 and discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On January 15, 2025, Mr. Venkatesan and representatives of Party D met in person and discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On January 21, 2025, Party D sent Mr. Venkatesan a letter containing a preliminary non-binding proposal to acquire