The fast advances of computer and sensor technologies have led researchers and artists to develop new opportunities for musical expression through the design of novel digital musical instruments and interactions (DMIs). One of the most critical challenge faced by DMIs designers, researchers and practitioners has been to account for learning and transmitting expertise related to their instrument. On the one hand, it is far from obvious how performers could reach expert skills in novel DMIs. On the other hand, it is not clear how DMIs could benefit to human learning, human development and well-being. In this workshop we aimed to bring together researchers, designers, and artists in order to better understand what are the issues underlying this challenge. We aim at identifying key research questions and suitable methods in order to tackle these issues.