Disclosed herein is an information processing apparatus that serves as a server that performs data transmission in response to receipt of media information from a user device. The information processing apparatus includes: an encrypted transmission data storage database that stores a transmission data identifier and encrypted transmission data such that the transmission data identifier and the encrypted transmission data are associated with each other; and a control section configured to acquire, from a key management server, an encrypted unit key obtained by encrypting a unit key that is used to encrypt the transmission data, and transmit the acquired encrypted unit key and the encrypted transmission data to the user device.