A disclosed information processing system includes a first terminal device used by a reporting user to post a reporting document; a second terminal device used by a user to transmit remuneration to the reporting user; and a document management device to manage the reporting document, wherein the first terminal device transmits the posting of the reporting document to the document management device, the second terminal device transmits, to the document management device, information about remuneration to be transmitted to the reporting user from a user who desires to transmit the remuneration to the reporting user, and the document management device identifies a destination for transmitting the remuneration to the reporting user from the posting of the reporting document, and executes an instruction to transmit the remuneration to the reporting user, based on the information about the remuneration and the identified destination.