Provided an information processing apparatus including a communication unit, an acquisition unit that acquires an application from an external storage apparatus each time processing concerning execution is started, a determination unit that determines whether the external storage apparatus acting as an acquisition source is registered, a first determination unit that determines whether to execute the application based on a user's operation if it is determined that the external storage apparatus is not registered, a communication processing unit that performs communication with an authentication server if the first determination unit determines to execute the application, a second determination unit that determines whether to execute the application based on an authentication result transmitted from the authentication server, and an execution processing unit that selectively executes the acquired application if the determination unit determines that the external storage apparatus is registered or the second determination unit determines to execute the application.