An information processing apparatus includes a communication unit and a controller. The communication unit is capable of communicating with another information processing apparatus via a relay server in a network. The controller is capable of obtaining communication environment information indicating a communication environment of the communication unit, the communication environment information including attribute information on a communication relay apparatus relaying communication between the communication unit and the relay server. Further, the controller is capable of calculating a sending interval to send maintenance signals to maintain connection with the relay server based on the obtained communication environment information. Further, the controller is capable of controlling the communication unit to send the maintenance signals to the relay server at the calculated sending interval.