#1 Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The RSUs vest and become exercisable on the first anniversary of the date of the grant subject to continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan), with accelerated prorated vesting upon a separation from service in accordance with the applicable award agreement.

#1 Represents Restricted Stock Units ("RSUs"), each of which represent a nontransferable right to receive one share of the Issuer's common stock. The RSUs vest in full on the first anniversary of date of the grant, subject to continued service (as defined in Cantaloupe, Inc's 2018 Equity Incentive Plan), with accelerated prorated vesting upon a separation of service in accordance with the applicable award agreement.

#1 The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions through a broker-dealer at prices ranging from $7.23 to $7.50. Douglas Bergeron (the "Reporting Person") undertakes to provide Cantaloupe, Inc. (the "Issuer"), any security holder of the Issuer, or the staff of the SEC, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote.

#2 The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions through a broker-dealer at prices ranging from $7.28 to $7.53. Douglas Bergeron (the "Reporting Person") undertakes to provide Cantaloupe, Inc. (the "Issuer"), any security holder of the Issuer, or the staff of the SEC, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote.

#1 The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions through a broker-dealer at prices ranging from $7.23 to $7.50. Douglas Bergeron (the "Reporting Person") undertakes to provide Cantaloupe, Inc. (the "Issuer"), any security holder of the Issuer, or the staff of the SEC, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote.

#2 The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions through a broker-dealer at prices ranging from $7.28 to $7.53. Douglas Bergeron (the "Reporting Person") undertakes to provide Cantaloupe, Inc. (the "Issuer"), any security holder of the Issuer, or the staff of the SEC, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote.