There is provided an information processing device including a data processing section configured to perform processing of playing back content according to a feature image, based on detection of the feature image from a captured image acquired by a capturing of an imaging section, and a specifying section configured to specify a resume point, which is a position of playing back the content, according to a timing at which the detection of the feature image is impossible. The data processing section performs the playback of the content from a position corresponding to the resume point, according to re-detection of the feature image after the detection of the feature image becomes impossible.