The largest population of youth at risk for involvement in the juvenile justice system are those with disabilities and mental illness. There has been scant research into the pathways that these students take from home, school and the community to involvement in the justice system in Australia. This paper utilises insights from critical disability studies, critical criminology, disability studies, and special education to identify the complex intersections of individual, social and systemic experiences for this group and to examine risk and success factors in the educational domain. Suggestions are offered for improvement, based on evidence-based practices and promising programs.