This article explores the relationship between school exclusion and youth crime and considers what criminological research can add to our understanding. The article first explores the history of the ways in which the criminological implications of school exclusion have been conceptualised, including the link between exclusion and young people’s offending, and the so-called ‘school-to-prison pipeline’. There is a long history of work in the UK and the US that explores how processes of school exclusion contribute to youth crime, the trajectory from the label of ‘troublemaker’ to more serious deviance, and how disciplinary polices can themselves lead to criminalisation. As we show, the relationship is complex and establishing causality is difficult. We then consider more recent work on how school exclusion contributes to the vulnerability and exploitation of marginalised young people. Finally, we argue for understanding young people’s lives, their educational experiences, and their involvement in offending, holistically and ‘in the round’, taking account of all their relationships and activities and employing contextual approaches to addressing these problems.