An information processing system, including: a portable communication device including a sensor that measures predetermined information and outputs a measurement result, the sensor having output characteristics varying depending on a place of use; and a information processing device for indoor use, which is communicatively connectable to the portable communication device, the information processing device being configured to: acquire the measurement result of the sensor from the communicatively-connected portable communication device; execute calibration of the sensor by using the acquired measurement result; execute an application program that uses the measurement result of the sensor; and performs determination as to whether or not the calibration has been executed for the communicatively-connected portable communication device when the application program is executed.