An information processing apparatus is configured to connect to a cloud server through a network, the cloud server including a plurality of servers providing a cloud service. The apparatus includes a memory to store connection destination information, and a plurality of network setting information lists, and circuitry to, in response to a user instruction for connecting the information processing apparatus to the cloud server, acquire the connection destination information, and the network setting information lists one by one in a descending order of probability, from the memory, to repeat operations of connecting the information processing apparatus to the cloud server using the acquired connection destination information and the acquired network setting information list until the connection is established with the cloud server, and notify a user of a progress status of the operations of connecting the information processing apparatus to the cloud server.
