Company: CTLPP
Filing Date: 2025-10-10
Form Type: DEF 14A
Source: 0001628280-25-044777
Chunk: 4

Company: CANTALOUPE, INC.
Filing Date: 2025-10-10
Form: DEF 14A
Chunk 4
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 or have had a transaction in the last twelve months. Included in the number of Active Devices are devices that communicate through other devices that communicate or transact with us.

(3) We define Recurring Revenue as the combination of our subscription and transaction revenue.

#### Operational Highlights
| •We entered into a Merger Agreement with 365 in June 2025, with the transaction expected to close in the first half of calendar 2026, subject to regulatory clearance under the HSR Act and the satisfaction or waiver of the other closing conditions in the Merger Agreement; 
 •We launched the AdVantage digital media program in October 2024, enabling brands to engage with consumers through digital advertising on our POS touchscreen devices across the U.S. and Canada;                                                                               
 •We introduced Smart Store, an advanced self-service retail solution designed to address labor shortages, theft, and shrinkage, while delivering a seamless consumer experience;                                                                                                
 •We expanded our presence in the sports and entertainment sector by signing the San Jose Earthquakes as a client for our POS technology solution and premium suites management system at their stadium;                                                                         
 •We launched Engage Pulse card readers for the arcade and amusement industry, offering a ladder pricing interface to maximize revenue potential and deliver a seamless payment experience for operators and consumers;                                                          
 •We collaborated with Fundbox to launch Cantaloupe Capital, providing small businesses with streamlined access to capital for equipment investments and flexible cash flow solutions; and                                                                                       
 •We enhanced financial flexibility by amending and expanding our credit facilities, increasing total borrowing capacity to support future growth initiatives.                                                                                                                   |

#### 62026Proxy Statement

#### Proxy Summary
This summary highlights selected information in this proxy statement. Please review the entire proxy statement and our Annual Report for the year ended June 30, 2025, before voting your shares.

#### Annual Meeting Information

#### How to Vote
| Internet                                                                            
 Before the meeting: www.proxyvote.com or scan the QR code located on the proxy card 
 During the meeting:                                                                 
 virtualshareholdermeeting.com/CTLP2026                                              |     | Phone          
 1-800-690-6903 |     | Mail                                                         
 sign, date and mail your proxy card in the envelope provided |

#### 72026Proxy Statement
Proxy Summary

| Proposal 1                                             
 Election of Directors                                  |     |            |
| The Board recommends a vote“FOR”each director nominee. |     | See page15 |

#### Director Nominees
| Director |     | Occupation