The Semantic Web seems to be a challenge for educational system aiming to accomplish the AAAL: Anytime, Anywhere, Anybody Learning. In this scenario an innovative e-learning solution named IWT, Intelligent Web Teacher, coming from Italian and European research projects, actually employed in many Italian high schools, enterprises and university departments, started to do it some years ago. IWT is able to model educational domains knowledge, users’ competences and preferences by a Semantic Web approach in order to create personalized and contextualized learning activities and to allow users to communicate, to cooperate, to dynamically create new content to deliver and information to share as well as enabling platform for e-learning 2.0