Disclosed herein is an information processing apparatus including a first holding section configured to hold a first patch file, a second holding section configured to hold a first hash value of each data block in a second patch file including a plurality of data blocks each having a predetermined block size, a hash value calculating section configured to calculate a first hash value of data corresponding to the block size in the first patch file, and a comparing section configured to compare the first hash value calculated by the hash value calculating section with the first hash value of each data block held in the second holding section, as a first-stage comparison process.