Company: CTLPP
Filing Date: 2025-06-16
Form Type: DEFA14A
Source: 0001104659-25-059928
Chunk: 1

Company: CANTALOUPE, INC.
Filing Date: 2025-06-16
Form: DEFA14A
Chunk 1
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 marketplaces, vending management
software, and smart store innovation.

365 brings deep, complementary expertise in micro markets, dining,
and POS solutions, particularly in closed-loop workplace environments. Together, we will offer a seamless, end-to-end solution for operators
across industries, enabling smarter, more connected, and more consumer-centric retail experiences.

Why This Matters

The strategic fit between Cantaloupe and 365 is strong. By joining
together, we are:

| · | Delivering                                                                                                                  
 Greater Value: This transaction will empower our joint customers to leverage the combined company’s comprehensive offerings 
 to best support their business, while leveraging integrations that unleash new product and innovation capabilities.         |

| · | Accelerating                                                                                                                           
 Innovation: With our IoT and software expertise and 365’s innovation and focus in user experience and kiosk technologies,              
 we have an unprecedented opportunity to build integrated tools, unify payment and loyalty platforms, and deliver deeper analytics that 
 truly move the needle for our customers.                                                                                               |

| · | Expanding                                                                                                                   
 Our Reach: Our complementary customer bases and geographic footprints allow us to scale faster and smarter. Together, we’ll 
 be able to serve more than 1.3 million operator locations across over 30 countries – unlocking new growth opportunities.    |

What it Means for You

I know news like this can raise questions and that’s completely
natural. Let me be clear: 365 chose to acquire Cantaloupe because of you: our culture of innovation, our commitment to customers,
and the speed at which we deliver results. That’s not changing. In fact, it’s the foundation of everything we have and will
build together.

Our teams, our people, and our shared purpose are and will be critical
to our future success.

What’s Next

The transaction is expected to close in the second half of 2025, pending
regulatory and shareholder approvals. In the meantime, it’s business as usual, and we will keep you informed as appropriate.

Today, at the internal all-hands meeting, we will further discuss this
transaction, address the opportunities it unlocks for our people and customers, and share more about what this means for our path forward.

Let me end with this: we’re entering a new phase of growth. This
is a defining moment for our company, and for all of us. Together with 365, we have the talent, the tools, and the momentum to redefine
the future of self-service commerce.

Thank you