Researchers note that the transitions of secondary students with disability in and out of the juvenile justice system are problematic for both the young person and leadership teams of their sending and receiving schools. Much of the literature focuses on barriers to successful transitions; however, there are some accounts of positive transition practices. In this article, we identify these positive practices and outline the steps school principals and executives involved in transitioning secondary school students with disability in and out of juvenile justice settings can take to smooth the way and improve student outcomes for this vulnerable population.