There is provided an information processing apparatus, an information processing method, a program, an information processing system, and a communication apparatus that are capable of enhancing authentication safety, the information processing apparatus including: a communication section configured to receive authentication information and a processing request from a first communication apparatus; an authentication information generation section configured to generate authentication information on the basis of first key information associated with a second communication apparatus; and a processing control section configured to control execution of a process corresponding to the processing request on the basis of the authentication information received by the communication section and the authentication information generated by the authentication information generation section.