One ojthe most closely investigated topics in e-leaniing research has always been the effectiveness of adaptive learning environments. The technological evolutions that have dramatically changed the educational world in the last si.x decades have allowed ever more advanced and smarter solutions lo 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 ihree different approaches adopted by the authors are discussed: these consist of a multi-agent system, an adaptive SCORM compliant package and an e-leaniing recommender svstem. Metadata " (supervisor prof Teresa Roselli). Her research interests are addressed to the elearningfteld, and in particular, to the definition of methodologies, specifications and software that can support educational processes and can allow a high level of didactic resource reuse and an adequate level of personalisation of learning path. She is author of many Journal and conference papers, both at national and international level, and she is part of international and national program committees. Maria Sinatra is full professor of General psychology and president of Second Level Degree in Design and Educational Management in the Digital Age at the University of Bari. After studying and working at the Goethe University in Frankfurt/M. (Germany), she turned her attention to the historical-epistemological reconstruction of psychology, as well as to the psychological aspects of mass media communication. On these subjects she has published numerous essays and various books. She has attended the following training courses: clinical and experimental psychology; family psychotherapy; hypnosis. She is member of the: ESHHS (European Society for the His-