A major issue problem in military training is the territorial dispersion of military personnel in a wide geographical area. Typically in every military training course, officers are gathered in training camps and attend the lessons. The specific model obliges officers to leave their position, their units to lose their ser-vices and is extremely costly, as the learners have to move and reside near the training camp during their training. The application of distance learning techniques seems in a position to solve such problems. The School of Research and Informatics of University of the Aegean (UoA), for Officers of the Greek Army in cooperation with the academic community in Greece studied the possibility of training military per-sonnel via a computer assisted distance-learning system and then implemented a pilot programme in Op-erational Business Management. The present chapter describes the results of this study, the experience acquired during the implementation and an overall assessment of the pilot program.