An information processing apparatus includes circuitry that: identifies one or more users; acquires information related to one or more external services provided by one or more external service group systems, based on the one or more users identified; generates, based on the information acquired from the external services, a plurality of options in generating identification information on an electronic file, the electronic file being generated by the information processing apparatus and to be transmitted to a transmission destination of each of the one or more identified users; displays the options in generating the identification information on the electronic file for selection; and transmits the electronic file to the transmission destination of each of the one or more identified users, using the identification information on the electronic file that is generated using the selected option.