The aim of the study was to identify transition planning processes as reported by participants for school-aged youth serving custodial sentences in New South Wales (NSW), Australia, and to establish the extent to which these reflect current evidence or research-based transition practices reported in the literature. The authors used inductive content analysis methodology to analyse interviews with 44 staff members from the education and juvenile justice systems in NSW. The findings of the study indicate that although a number of evidence/research-based practices are being used, there are some that still need to be implemented. Specifically, there is a need for more involvement of the families of incarcerated youth and support for the self-determination of the young people in custody.