Learning ecosystems are getting smarter and play a central role in regional development and social innovation. “Smart,” thus, are not simply technology-enhanced learning ecosystems but, rather, learning ecosystems that promote the multidimensional well-being of all players of learning processes (i.e., students, professors, administrative personnel and technicians, territorial stakeholders, and, for the schools, parents) and that contribute to the increase of the social capital of a “region,” also thanks to the mediation of the technologies.