This chapter is based on an empirical study of teachers’ experiences with a range of educational technologies. The study looks at net-based communication between students and between students and teachers in the master education programme course “IT educational design”. We study how the course experiments with different technologies with the intention both of attracting students from all over the country and of supporting students’ and students/teachers’ collaborative activities, sharings and discussions. We ask: How can technologies facilitate communication and learning in different teaching environments? The sub-questions are: (1) what categories of communication appear in different communication forums; (2) what do the findings indicate when the focus is on pedagogic and didactic perspectives; and (3) what initiatives follow in net-based communication in higher education? Thus we are aiming at reflecting the meaning of a digitally influenced form of Academic Bildung, in which the net-based tools used, and not their human counterparts, are of special interest to us.