An information processing system includes a server including first circuitry and a first memory and an information processing apparatus including second circuitry and connectable to the server via a communication network. The second circuitry of the information processing apparatus acquires, as logged-in user information, information input by a user when logging in to the information processing apparatus, and transmits the logged-in user information to the server. The first circuitry of the server stores the logged-in user information in the first memory, acquires a user request to the information processing apparatus based on audio information of voice input via a terminal, converts user identifying information in the user request into the logged-in user information, and transmits the user request including the logged-in user information to the information processing apparatus to instruct the information processing apparatus to execute the user request.