Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 334

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 334
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C-9</div>

TABLE OF CONTENTS

In Witness Whereof , the parties have caused this Agreement to be executed as of the date first written above.

| 365Retail Markets, LLC  |
| By: /s/ Joseph Hessling |
| Joseph Hessling         |
| Name                    |
| Chief Executive Officer |
| Title                   |

Signature Page to Voting and Support Agreement C-10

TABLE OF CONTENTS

| Shareholder                                     |
| HUDSON EXECUTIVE CAPITAL LP                     |
| BY: HEC MANAGEMENT GP, LLC, ITS GENERAL PARTNER |
| /s/ Douglas L. Braunstein                       |
| Signature                                       |
| Douglas L. Braunstein                           |
| Printed Name                                    |
| Address:                                        |
| [***********]                                   |
| Email Address:                                  |
| [***********]                                   |

| Shareholder                                     |
| HEC MASTER FUND L.P.                            |
| BY: HEC PERFORMANCE GP LLC, ITS GENERAL PARTNER |
| BY: HEC MANAGEMENT GP LLC, ITS MANAGING MEMBER  |
| /s/ Douglas L. Braunstein                       |
| Signature                                       |
| Douglas L. Braunstein                           |
| Printed Name                                    |
| Address:                                        |
| [***********]                                   |
| Email Address:                                  |
| [***********]                                   |

Signature Page to Voting and Support Agreement C-11

TABLE OF CONTENTS

| Shareholder               |
| /s/ Douglas L. Braunstein |
| Signature                 |
| Douglas L. Braunstein     |
| Printed Name              |
| Address:                  |
| [***********]             |
| Email Address:            |
| [***********]             |

| Shareholder                |     | Shares Held Of 
         Record |     | Company Equity 
 Awards         |     |   Additional 
   Securities 
 Beneficially 
        Owned |
| Hec Master FundLP          |     |      9,270,694 |     | N/A            |     |          N/A |
| Hudson Executive CapitalLP |     |         48,678 |     | N/A            |     |    9,270,694 |
| Douglas L. Braunstein      |     |         20,212 |     | N/A            |     |    9,270,694 |

Signature Page to Voting and Support Agreement C-12

#### TABLE OF CONTENTS

#### Annex D

### VOTING AND SUPPORT AGRE