Provided is an information processing system which includes: a communication device including a sensor that measures information regarding a posture thereof; and an information processing device. The information processing device displays a guide image for causing a user to perform a rotational operation for rotating the communication device, and executes calibration of the sensor by using the measurement result of the sensor acquired from the communication device while the guide image is displayed. The guide image includes an image representing a reference axis to be a rotation center for the rotational operation and an image representing the communication device, and the image representing the communication device is located within the guide image so that a portion of the communication device corresponding to a position of the sensor overlaps with the reference axis.