Patent ID: 8112592

Claim:
An information processing apparatus, comprising: a storage unit configured to store a plurality of content data and a user-specified rule, the user-specified rule regarding content data to be directly transferred to a registered portable device from the information processing apparatus and being associated with a registered portable device ID identifying the registered portable device; a communication unit configured to connect to a portable device including a portable device ID; a detection unit configured to detect a direct local connection to the portable device; and a control unit configured to determine, when the connection to the portable device is detected, whether the portable device ID matches the registered portable device ID and, when the portable device ID and the registered portable device ID match, to automatically extract selected content data out of the plurality of content data of the storage unit according to the user-specified rule defining criteria, set in advance of transfer of the selected content data held on the information processing apparatus and prior to the detection of the connection, for identifying the selected content data, in response to the registered portable device being connected to the information processing apparatus, wherein the communication unit is configured to transfer the selected content data extracted from the storage unit to the portable device independent of a user's designation of the selected content data after the detection unit detects that the portable device is connected to the information processing apparatus.