Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 127

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 127
---
 or otherwise in connection with any tender or exchange offer.

Notwithstanding the foregoing, each of the Supporting Shareholders may Transfer Subject Securities: (a) if such Supporting Shareholder is an individual, (i) to any member of such Supporting Shareholder’s immediate family, (ii) upon the death of such Supporting Shareholder, (iii) to any trust for the direct or indirect benefit of such Supporting Shareholder or the immediate family of such Supporting Shareholder for bona fide estate planning purposes or (iv) to a partnership, limited liability company or other entity of which such Supporting Shareholder and/or the immediate family of such Supporting Shareholder are the legal and beneficial owners of all the outstanding equity securities or similar interests; or (b) if such Supporting Shareholder is a corporation, partnership, trust, limited liability company or other business entity, (x) to another corporation, partnership, trust, limited liability company or other business entity that is an affiliate controlled by such Supporting Shareholder, (y) to one or more partners or members of such Supporting Shareholder or to an affiliate under common control with such Supporting Shareholder or (z) to any investment fund or other entity controlling, controlled by, managing or managed by or under common control with such Supporting Shareholder or affiliates of such Supporting Shareholder (including, for the avoidance of doubt, where such Supporting Shareholder is a partnership, to its general partner or a successor partnership or fund, or any other funds managed by such partnership); provided, however, that a Transfer referred to in this sentence will be permitted only if, as a precondition to such Transfer, the transferee agrees in a written document, reasonably satisfactory in form and substance to 365, to be bound by all of the terms of the Voting Agreement.

<div align='center'>62</div>

#### TABLE OF CONTENTS
Reimbursement of Hudson

Cantaloupe has agreed to reimburse Hudson and its directors, officers, employees and agents acting on Hudson’s behalf for out-of-pocket expenses incurred by them, as such expenses are incurred, whether such expenses were incurred prior to or after June 15, 2025, in connection with the negotiation, execution and performance of the Voting Agreement and any claims arising out of, related to or involving the Voting Agreement (including without limitation, reasonable fees and expenses of counsel), in each case except in the case of willful and material breach by Hudson or such representatives.

<div align='center'>63</div>

#### TABLE OF CONTENTS

### THE MERGER AGREEMENT