The present invention relates to information processing apparatuses. A content to be checked out is stored in an automatic-checking-out-destination storage section 113 from musical-piece-file storage sections 108-1 and 108-2 for each external-unit/-medium ID which identifies a PD 5. A GUI section 101 determines through a transfer processing section 103 and a PD plug-in 111 whether the PD 5 has been connected. When it is determined that the PD 5 has been connected, a musical-piece file is checked out from the musical-piece-file storage sections 108 to the PD 5 through a musical-piece management section 104, a file search section 106, and a data base 107 according to the information of the content to be checked out stored in the automatic-checking-out-destination storage section 113. The present invention can be applied to music reproduction software.