This article frames and theorises the nature of adolescents' informal experiences in Web 2.0 environments to articulate their fit or misfit with current conceptions of school education and educational practices. Adolescents are increasingly active Web 2.0 users. However, the traditional research and education communities have been slow to respond to the rapid emergence of the digital generational culture. Adolescents' new ways of interacting and producing could possibly render current configurations of schooling obsolete and hence require new conceptualisations of schooling. While scenarios for schooling in the future have been broadly discussed by educators, little analysis exists of the possible impact on these scenarios of adolescents' engagement with Web 2.0 spaces. This article discusses how these new visions might influence, disrupt and interact with future schooling scenarios and educational practices.