There is provided an information processing system having a first terminal, a second terminal, and a wireless communication device which wirelessly connects the first terminal and the second terminal with each other for communication, where the first terminal and the second terminal respectively have a file system, the information processing system including a GUI providing unit that provides a display screen of the second terminal with a GUI of the file system, an operation reception unit that receives a user operation carried out on a GUI screen provided by the GUI providing unit, an operation determination unit that determines whether the user operation received by the operation reception unit is an operation relating to the first terminal or not, and an activation unit that, upon the operation determination unit determining that the user operation is an operation relating to the first terminal, controls the wireless communication device to transmit an instruction to turn on a power supply of the first terminal to the first terminal, and simultaneously carries out a process to wirelessly connect the first terminal and the second terminal with each other via the wireless communication device.