A printing system includes a printing device including a thermal head that prints print content on a print medium; and an information processing apparatus that controls the printing device. The information processing apparatus comprises a processor configured to detect, from print image data from a server, a position of a control target portion including a specific portion in a print image corresponding to the print image data. The processor is configured to generate printing control information for printing the control target portion. The processor is configured to transmit the print image data, the position of the control target portion, and the printing control information to the printing device. The printing device executes different printing controls for the control target portion and a portion other than the control target portion based on the print image data, the position of the control target portion, and the printing control information.