Despite the ongoing discourse about the constantly connected and digitally savvy youth in the UK, a growing evidence base demonstrates that there are still significant inequalities in young people's ability to access and use the internet. There is a small, but significant, proportion of young people who do not have internet access at home, nor have sufficient digital skills to engage online in ways that are meaningful to them. This paper presents findings from a two-year school and local council-run initiative in England to provide 30 such digitally disadvantaged young people with a laptop and stable internet connection at home as well as school support. Drawing on rich qualitative data (home and school visits; parent, student, and teacher interviews), we explore the experiences of young people, parents, and teachers who were part of this digital inclusion scheme. Specifically, we examine how the long-standing essentialist discourses around "digital youth" and determinist ideas of technology and social change inform how such a scheme is perceived, enacted, and experienced by the teachers, parents, and young people involved with the initiative, as well as the implications these discourses have for the ways the outcomes of such projects are judged.