A server of a printing system includes a print instruction acquisition unit configured to acquire a print instruction indicated by a voice that is a print instruction of a content included in a content group from a voice intermediation device, a selection unit configured to select a content to be printed from the content group according to the print instruction, and a transmitter configured to transmit print data for printing the selected content to the printing device. The selection unit totalizes a printing count of each content included in the content group for a plurality of users, and selects the content to be printed from the content group based on the totalized printing count. The selection unit may select the content to be printed from the content group based on an attribute applicable to a user. The printing device receives the print data and performs printing according to the print data.