This report draws on 53 focus group interviews conducted with students aged 13 and 15 in both representative and innovating UK secondary schools. The schedule for these discussions covered a wide range of issues relating to the use of Web 2.0 services both in and out of school. These young people were often deeply engaged with this technology and broadly positive as to that experience. However, they also identified a shared set of circumstances associated with its use (or potential use) in school that could be variously stressful, frustrating, threatening or devious. It is argued that the social and cognitive practices young people cultivate through the recreational use of Web 2.0 tools and services should not be regarded as general competencies. Rather those practices will be shaped and constrained by the particular socio-cultural settings in which such tools are used. If neither students nor teachers are firmly embracing Web 2.0 in the settings of education, then this may reflect tensions that exist between different ambitions and expectations associated with in-school versus out-of-school cultures. If adoption of Web 2.0 in education remains modest, the present perspective goes beyond merely denying a rhetoric of the "digital native". Moreover, these findings suggest a sophisticated awareness among young people of institutional, social and moral tensions associated with modern web-based services, as well as a greater level of ambiguity of attitude than is normally recognised. (Contains 1 table.)