There is provided an information processing apparatus, the information processing apparatus including: a control unit configured to cause a second information processing apparatus to output authentication key information for allowing a first information processing apparatus to make a wireless connection with the second information processing apparatus in order to conduct data transmission from the first information processing apparatus to the second information processing apparatus using wireless communication, and determine to allow the first information processing apparatus to make the wireless connection on the basis of authentication key information input into the first information processing apparatus and the output authentication key information.