Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 34

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 34
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 Dumbrell and 365 or its affiliates regarding such potential rollovers. Other than as described above, none of 365, Holdco, Holdco II, Merger Subsidiary or any of their respective affiliates has entered into any agreements, arrangements or understandings with respect to rollover shares. |

| • | Prior to the effective time of the Merger, certain of our executive officers may enter into new employment arrangements with 365 that would become effective upon the closing of the Merger. As of the date of this proxy statement, none of our executive officers have entered into any arrangements with 365 with respect to their employment. |

Please see the section of this proxy statement titled “ The Merger—Interests of Certain Persons in the Merger” for additional information about these financial interests.

| Q: | Have any Cantaloupe shareholders already agreed to approve the Merger? |

| A: | Yes. Each member of the Board and Hudson, collectively representing approximately 17.9% of the voting power |

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of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting, have entered into Voting Agreements with 365 to, among other things, vote in favor of the proposals set forth in this proxy statement. For more information, see the section of this proxy statement titled “ The Merger—Voting Agreements”.

| Q: | Is the Merger subject to the satisfaction of any conditions? |

| A: | Yes. The Merger is subject to the satisfaction of various conditions, including (i) approval and adoption of the Merger Agreement by a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class, and (ii) the expiration or termination of the applicable waiting period under the HSR Act. The Merger is not conditioned upon the receipt of any financing. For a description of these conditions as well as other conditions to the Merger, please see the section of this proxy statement titled “The Merger Agreement—Conditions to Completion of the Merger”. |

| Q: | Who is entitled to vote at the Special Meeting? |

| A: | All holders of common stock and preferred stock of record as of the close of business on July 21, 2025, the record date for the Special Meeting, are entitled to vote