One of the most closely investigated topics in e-learning research has always been the effectiveness of adaptive learning environments. The technological evolutions that have dramatically changed the educational world in the last six decades have allowed ever more advanced and smarter solutions to be proposed. The focus of this paper is to depict the three main dimensions that have driven research in the e-learning field and the evolution of the technological approaches adopted for the purposes of building advanced educational environments for distance learning. Then, the three different approaches adopted by the authors are discussed; these consist of a multi-agent system, an adaptive SCORM compliant package and an e-learning recommender system.