[Object] To propose an information processing device, an information processing method, and a program capable of efficiently transmitting captured images between devices connected via a network even when a moving image or a plurality of still images are captured as a series of images.[Solution] The information processing device includes: an acquisition unit configured to acquire a series of images captured by an imaging unit in accordance with a predetermined operation mode on the basis of an instruction from an external device connected via a network; and a transmission control unit configured to transmit a series of thumbnail images corresponding to the series of images to the external device via the network. The transmission control unit transmits at least some of the series of images to the external device via the network in accordance with an instruction from the external device to which the series of thumbnail images has been transmitted.