An information processing system includes: one or more information processing apparatuses; and a management server, in which the management server includes a license key table management unit that receives inputs of a serial number, an application ID, and a license key from an administrator and registers them in a license key table, and a license key authentication unit that extracts the corresponding license key from the license key table by using the application ID and the serial number received from the information processing apparatus in which the application program is installed, and performs license key authentication of the application program by using the extracted license key, and the one or more information processing apparatuses each include an application installation unit that installs the application program, and an authentication requesting unit that transmits the application ID and the serial number to the management server to request for license key authentication.