The General Secretariat for Lifelong Learning and Youth (GSLLLY), the strategic national entity for Adult Education in Greece, has designed and implemented various e-learning courses offering flexibility beyond time and space restrictions. The courses run in two consecutive periods, the first one from 2008 to 2011 and the second one from 2014 to 2016. This paper is focusing on key design and implementation features of the courses in both periods and is analyzing the ways and the level by which the evaluation of the courses of the first period affected positively the design of the courses in the second period by enhancing the strengths and rectifying the weaknesses. Further on the evaluation results of the second period courses clearly showed that the majority of the first period problems have been solved and provided useful material for further improvement.