A printing system includes a printer and an information processing device that includes a processor and a memory storing processor-executable instructions, the instructions being configured to, when executed by the processor, cause the processor to, when condition information does not include trigger information, determine to instruct the printer to start a pre-printing operation, when the condition information includes the trigger information, determine not to instruct the printer to start a pre-printing operation, in response to determining to instruct the printer to start the pre-printing operation, transmit the preparation instruction information to the printer, in response to determining to instruct the printer to start the pre-printing operation and performing the preparation instruction process, generate print data based on specified contents data, and transmit the print instruction information to the printer.