Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 16

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 16
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 Agreement and the transactions contemplated thereby, we currently expect that each of our executive officers will vote all of their respective shares in favor of each of the proposals.

#### Voting Agreements (Page62)
Concurrently with Cantaloupe’s, 365’s, Holdco’s, Holdco II’s and Merger Subsidiary’s entry into the Merger Agreement, each member of the Board and Hudson Executive Capital LP (which we refer to as “Hudson” and, together with each member of the Board, as the “Supporting Shareholders”), who collectively represent approximately 17.9% of the voting power of the Cantaloupe stock, have entered into Voting Agreements with 365. Pursuant to and subject to the terms of the Voting Agreements, the Supporting Shareholders have agreed to, among other things, (a) vote in favor of (i) the proposals set forth in this proxy statement and (ii) each of the other actions contemplated by the Merger Agreement, (b) vote against any action or agreement that would result in a breach of any representation, warranty, covenant or obligation of Cantaloupe in the Merger Agreement and (c) vote against the following actions (other than all actions and transactions contemplated by the Merger Agreement, including the Merger, and the Voting Agreement): (i) any change in the Board; (ii) any action or proposal to amend, or waive any provision of the Cantaloupe Articles or the Second Amended and Restated Bylaws of Cantaloupe (which we refer to

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#### TABLE OF CONTENTS
as the “Cantaloupe Bylaws”); (iii) any Acquisition Proposal (as defined in the section of this proxy statement titled “ The Merger Agreement—No Solicitation of Acquisition Proposals; Changes in Board Recommendation ”) or any agreement related thereto, and any action in furtherance of any Acquisition Proposal and (iv) any other action which is intended, or would reasonably be expected, to result in any of the conditions to the consummation of the Merger under the Merger Agreement not being fulfilled.

The Voting Agreements will automatically terminate and become void and of no further force or effect at the earliest of: (a) the effective time of the Merger; (b) the date on which the Merger Agreement is validly terminated in accordance with its terms; and (c) the date of any modification, waiver or amendment to