This essay tries to trace the most important steps of Italian e-learning between 1995 and 2005, a crucial time for the success of the Distance Learning in Italy. From the first degree course entirely in e-learning (by the Politecnico di Milano) some excellence e-learning centers of research and experimentation were born until the institutionalization of the telematic universities, and in these years they laid the basis of the actual e-learning panorama. Despite the technologic, infrastructural and cultural gap with other European countries and in accordance with the evolution of pedagogical models between 1995 and 2005, e-learning became an increasingly high value option for almost all the University community.