There is provided an information processing apparatus including an operation recognition unit configured to recognize a drag start area in a first application and a droppable area in a second application, the drag start area being an area where an drag operation is started, and the second application being different from the first application, a paste content processing unit configured to analyze attributes of the drag start area and the droppable area, and to determine a paste content in response to a comparison result between the respective attributes, and a paste execution unit configured to paste the paste content determined by the paste content processing unit, in the droppable area, when the operation recognition unit recognizes a drop operation in the droppable area.