This paper focuses on the meaning of digital inclusion and its relationship to the use of one-to-one technology in didactics. It criticizes current approaches to digital inclusion as being mainly deterministic, starting from a too simple criterion of access as material availability of technology, and failing to consider the many origins and consequences of cultural differences in access to Information and Communication Technologies (ICT). Three case studies on one-to-one programs conducted in Italy, Ethiopia and Brazil between 2009 and 2012 are used to illustrate the capability of these initiatives to effectively change teaching and learning practices, and foster digital literacy. The main questions are whether digital inclusion takes place in the contexts where one-to-one technology was launched, and what the best conditions are to make meaningful use of these devices, both for the students and the teachers involved. While reflecting on one-to-one goals and achievements, the paper touches transversally upon three problematic issues: the importance of meaningful access to technology, the crucial role of context in adopting new technologies and the policies that should be advanced to enhance digital inclusion. The framework for sustainable one-to-one programs that we propose is a digital inclusion concept based on cultural needs analysis, alongside the enhancement of social and human capital for innovation in teaching practices.