This study explored the nature of disengagement in young people serving custodial sentences. This was in order to gain new theoretical insights into strategies for their reengagement with education. This is because 90% of young offenders who drop out of school prior to incarceration are reportedly disengaged (dropout being an indicator of disengagement). This paper reports on a qualitative ethnographic case study in one secure children's home in England. Semi-structured interviews with 16 incarcerated young people were conducted from which five participated in in-depth case studies along with teachers and care staff. Data were collected as participants engaged with a learning opportunity over a period of time. Extending emerging theory of disengagement, findings showed that disengagement oscillated between both active and passive forms within the same individual and pointed to the need for a range of strategies needed for reengagement. This paper suggests that disengagement is complex where the physical and social context shapes how disengagement manifests. This has pedagogical implications for education in custodial settings and other at-risk children in alternative or mainstream education provision.