There is provided an information processing apparatus including a communication unit that transmits content to a communication terminal connected via a network and a control unit that controls transmission of the content by the communication unit. The control unit causes the communication unit to transmit a first file containing the content for a time corresponding to a communication disabled time of the communication terminal in response to a transmission request of the content from the communication terminal and causes the communication unit to transmit a second file to be transmitted subsequent to the first file at a transmission predetermined time obtained by adding the communication disabled time of the communication terminal to a transmission time of the first file.