An apparatus of this invention is directed to an information processing apparatus that aims to improve the quality of the ITC education based on the history of reactions or evaluations to education conducted by different educators to different educatees in different education site environments in education using education application software. An information processing apparatus includes an education site history accumulator that accumulates the history of pieces of education site information representing the reactions or evaluations of education site participants including an educator and an educatee at an education site using an education application software, and the education application software in association with each other, an education site information receiver that receives, from a communication terminal, the pieces of education site information acquired by the communication terminal or a device connected to the communication terminal, and an analysis information generator that generates analysis information of the education site from the received pieces of education site information and the history of the pieces of education site information.