Theories of radical or critical pedagogy have emphasized the importance of relating educational work to broader social movements although this has not been developed in detail. The recent history of community publishing and worker writing workshops in Britain helps to illuminate how these ideas have been adapted in a number of informal settings. Using archive materials, interviews with activists and my personal experience I explore some dilemmas and tensions within the idea of radical pedagogy. In particular, attempts to reconfigure relations between writers/students and organizers/tutors, as well as the role of personal experience, are examined in relation to both organizational and wider societal relations. These interventions faced many challenges but were not completely undermined.