One of the major shortcomings of modern e-learning schemes is the fact that they significantly lack on user personalization and educational content representation issues. Semi- or fully automated extraction of user profiles based on users’ usage history records forms a challenging problem, especially when used under the e-learning perspective. In this chapter we present the design and implementation of such a user profile-based framework, where educational content is matched against its environmental context, in order to be adapted to the end users’ needs and qualifications. Our effort applies clustering techniques on an integrated e-learning system to provide efficient user profile extraction and results are promising.