A printing system includes: a printing device; and a data processing server. A first controller of the printing device is configured to perform: a reading process to read a reading target to generate image data; a determination process to determine whether to transmit the image data to the data processing server according to at least one of available capacity information and capacity-related information; and a data transmission process to transmit the image data to the data processing server. A second controller of the data processing server is configured to perform: a payment-related process related to a fee payment for printing based on the image data. The first controller is configured to further perform, after the fee payment is completed: an acquisition process to acquire print data corresponding to the image data; and a printing process to form an image corresponding to the print data on a printing medium.