The present technology relates to an information processing device and an information processing system which enable setting for establishing connection to a wireless LAN in a simple manner. The present technology includes a user interface that receives a user input concerning connection setting of a second communication path of another information processing device, a communication section that exchanges a command with the other information processing device via a predetermined server by using a first communication path, on the basis of the user input, and a processing section that processes the command. The command includes information that is necessary for the other information processing device to establish the second communication path. The present technology is applicable to an information processing device that performs setting for an IoT (Internet of Things) terminal, for example.