PROBLEM TO BE SOLVED: To provide an information processing device, information processing method, and program that allow a wearable device to be fitted to a user in a proper fitting feeling.SOLUTION: An information processing device has a determination unit 31 and an output unit 32. The determination unit 31 determines the holding state of a wearable device on a fitting object, on the basis of information on the usage state of the wearable device. The output unit 32 generates and outputs control information for implementing the determined holding state.SELECTED DRAWING: Figure 2COPYRIGHT: (C)2018,JPO&INPIT