There is provided an information processing apparatus that is connected to a server for managing data, the information processing apparatus including a data storage configured to store the data obtained from the server, a check unit configured to check a cumulative state of change history information indicating a change type of the data in the server stored in the server, and a data obtaining unit configured to use a check result of the check unit as a basis to determine an obtaining method by selecting either a first obtaining method of synchronizing the data stored in the data storage with the data managed by the server in accordance with the change history information or a second obtaining method of obtaining, from the server, data presence information indicating the data existing in the server to synchronize the data stored in the data storage and to obtain the data from the server.