A content distribution server according to an embodiment includes a storage unit that stores: store codes corresponding to stores that are targets of distribution, device codes corresponding to receipt issuing devices in each respective store, print specifications corresponding to each receipt issuing device, and additional information items, each including print specifications required for printing the respective additional information. A control unit identifies at least one additional information item for transmitting to one or more of the stores having one or more receipt issuing devices with corresponding print specifications that match the print specifications of the at least one additional information item. A communication interface transmits, to the corresponding one or more stores, the identified at least one additional information and instructions causing the one or more receipt issuing devices in the one or more stores to print receipts including an image corresponding to the transmitted at least one additional information item.