An information processing system including a selection unit that selects one or more pieces of content in a use status that meets a predetermined condition in a specific period, an extraction unit that extracts, as a feature value of the content, information associated with one or more pieces of material data used at the time of generation of the content, on the basis of metadata added to each piece of the selected content, and a generation unit that generates support information for a user on the basis of the extracted feature value.