This article presents two case studies of marginalized youth experimenting with digital music production in flexible education settings. The cases were drawn from a 3-year study of alternative assessment in flexible learning centres for youth who have left formal schooling in Queensland, Australia. The educational issues are framed by reference to the literature on cultural studies approaches to education and the digital arts. Each case describes the student's histories, cultural background and experiences, music productions, evidence of learning and re-engagement with education. Online judgements and blog comments about the digital music production are theorized as social fields of exchange. Findings document how digital music production can re-engage and extend participation. The study questions the adequacy of current approaches to evaluating and accounting for the learning and development of youth in flexible education contexts. It makes the case for educators to view popular music and video production as curriculum fields, where training, aesthetic and skill-based valuations and distinctions are exchanged between performers, performances and audiences.