Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 108

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 108
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 shares.

Following the execution of the Merger Agreement, representatives of 365 have had preliminary discussions with Douglas G. Bergeron, Chairman of the Board, regarding a potential rollover arrangement with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron, which shares are expected to be rollover shares for purposes of the Merger Agreement. As of [ ], 2025, the record date for the Special Meeting, Mr. Bergeron beneficially owned 1,152,559 shares of common stock, representing approximately [ ]% of the voting power of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting. Based on preliminary discussions held to date, 365 expects that, prior to the closing of the Merger, Mr. Bergeron will enter into a rollover agreement with 365 or one of its affiliates with respect to shares of common stock held by him. However, as of the date of this proxy statement, there is no understanding as to the amount of shares of Cantaloupe’s common stock that would be subject to such rollover arrangement, and no definitive agreement has been entered into between Mr. Bergeron and 365 or its affiliates regarding such potential rollover, and there can be no assurances that the terms of any such agreement will be agreed upon with Mr. Bergeron. If Mr. Bergeron and 365 or its affiliates enter into a rollover agreement, Mr. Bergeron will not receive the merger consideration in respect of any rollover shares held by him and instead such shares will, immediately prior to the effective time of the Merger, be subject to the treatment specified under the rollover agreement applicable to such rollover shares. Based on preliminary discussions held to date, if Mr. Bergeron and 365 or its affiliates enter into a rollover agreement, Mr. Bergeron may obtain a seat on the board of directors of an affiliate of Providence that will oversee the management of 365 following the closing of the Merger.

Other than as described above, as of the date of this proxy statement, none of Cantaloupe’s directors or executive officers has entered into any new agreement, arrangement or understanding with 365 or any of its affiliates regarding the terms and conditions of compensation, incentive pay or employment with Cantaloupe after the Merger or any

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rollover agreement. Prior to or following the effective time of the Mer