Education is seen as performing a variety of functions, but the socialization of young people into conforming to norms of behavior is a high priority. Yet, the two principal educational risk factors identified for offending appear to be low attainment and weak engagement in school, culminating in complete detachment. It is argued that there is an ill-defined group of young people plagued by multiple disadvantages who usually have difficulties gaining access to, participating in, and progressing within mainstream education. It is concluded that there is a deep-rooted cultural mismatch between the youth justice and education systems. The very different professional backgrounds, environments, and objectives lead to collective behaviors that often tend to detach young people who offend from mainstream education, constituting as barriers to reintegration. However, could the ‘What Works’ movement provide a bridge across the cultural divide between youth justice and education? The most likely response by policymakers is to continue to conceptualize the problem as the inherent difficulties of the young person and to conceive of offenders as a discrete category of learners. Research is recommended in three areas: (1) establish basic educational demographics of the youth justice system; (2) chart the educational exclusion careers of young people in the context of their involvement in the care and criminal justice system; and (3) determine points of intervention, understand better the processes of detachment, and develop robust evaluations of what works. Figures, glossary and references