The book explores advances in soft-skill training through the adaptation of traditional psycho-pedagogical methodology to digital and online settings. Several educational techniques are explored, such as role-playing, psychodrama and rule and drama-based games. The experiences reported in the book are the synthesis of several European projects, coordinated by the authors, aimed at applying known psycho-pedagogical training models to on-line, technology enhanced learning contexts in a broad range of applications and target groups. The specificity of such a psycho-pedagogical methodology, applied throughout all the discussed EU projects, is mainly represented by the importance of feedback and debriefing processes that can be conveyed to learners through different means, such as online group or individual chat with tutors, automatic reports and a psychologically informed scoring system. Tutors, either real or artificial, are seen as the key factor facilitating the training process. The ultimate objective of this book is to offer a theoretical framework where real examples, direct experiences and possible indications on how rule and drama-based multiplayer and single player games can support traditional practice for enhancing soft skills to a wide community of trainers, coaches, HR advisors, consultants and psychologists.