Using data from a qualitative study exploring the intersections of school exclusion, mental health, and involvement in criminal behaviour, we explore young people’s experience of schools to inform consideration of how schools might be modified to help improve mental health and engagement, and take a more proactive role in safeguarding young people from contextual risks. We draw on sociological theories considering how inequity and disadvantage may be reproduced. Poor experiences of school create disengagement, perpetuate deep structural inequalities, and can act as a motivating force to gain status and money through the illicit economy. Broadening the focus in schools, away from the narrow pursuit of academia, to include more group-based and project-based learning; placing greater priority on life skills and vocational training; and focussing more on developing a sense of belonging through sports and arts may benefit all students, particularly those most at risk of exclusion. If the education system is to build stronger engagement with the most marginalised students, it must actively support them to achieve their priority to find (legitimate) means of earning money.