An information processing apparatus, an information processing method, and an information processing system. The information processing apparatus is provided with one or more memories that store state information indicating a predetermined state of an object, identification information for an image or video that represents a mode of the predetermined state, and document information including a description describing the mode represented by the image or video, and circuitry that receives from the communication terminal, a search input, transmits to the communication terminal, first screen information of a search result list screen indicating an image or video identified by the identification information of the image or video stored with the state information specified based on the input, receives from the communication terminal, information for specifying an image or video selected by a user, generates description information including a description in the document information stored in association with identification information for the image or video, and transmits the description information to the communication terminal.