A content transfer system composed of a content reproduction terminal and an information processing apparatus is disclosed. A storage section stores information representing a file format and a bit rate of content reproducible by the reproduction terminal. A transmission section transmits the information stored in the storage section to the information processing apparatus. An obtainment section obtains the information representing the file format and the bit rate of the content reproducible by the reproduction terminal therefrom. A conversion section converts content having a predetermined file format and a predetermined bit rate as a transfer target into content having the file format and the bit rate represented by the information obtained by the obtainment section. A transfer section transfers the content converted by the conversion section to the reproduction terminal.