This chapter discusses current research on educational efforts to connect school learning with young people’s digital practices in- and out-of-school. Instead of focusing on divides between in-school and out-of-school learning or between the “digital generation” and other age groups, in this chapter we discuss what recent research says about the ways in which school can become a space in which young people’s digital practices can transformatively converge with schooling, and how this convergence is related to their learning and identity building. We begin our narrative reflection of current research by focusing on the myth of digital natives. Next, we will conceptualize recent efforts to researching and understanding young people’s engagement, learning and identity building across sites and contexts. We will then turn to illuminating some key rationales of current educational research on creating convergence in young people’s social ecologies via the use of digital technologies and media. We conclude our reflections by pointing out that although there are some promising findings on how digital technologies and media can create convergence in young people’s engagement and learning across sites and contexts, less research attention is given to young people’s personal sense-making and self-making mediated by their digital practices, and how formal education could build on those practices for academic, vocational and/or civic ends.