In this chapter we show the technical and methodological aspects of an e-learning platform for automatic course personalization built during the European funded project Diogene. The system we propose is composed of different knowledge modules and some inference tools. The knowledge modules represent the system’s information about both the domain-specific didactic material and the student model. By exploiting such information the system automatically builds courses whose didactic material is customized to meet the current student’s degree of knowledge and her/his learning preferences. Concerning the latter, we have adopted the Felder and Silverman’s pedagogical approach in order to match the student’s learning styles with the system Learning Objects’ types. Finally, we take care to describe the system’s didactic material by means of some present standards for e-learning in order to allow knowledge sharing with other e-learning platforms and knowledge searching by means of possible Semantic Web information retrieval facilities.