National rates of juvenile incarceration show that about 33% of the population in correctional confinement has disabilities such as behavioral disorders or specific learning disabilities. All students identified under the Individuals with Disabilities Education Improvement Act (IDEIA) as having a disability are entitled to special education and transition services when they are incarcerated if they need specialized services. Despite the requirements for education and transition, research shows that rates of recidivism increase from about 55% for the general population of incarcerated youth to approximately 85% for youth with disabilities. This article addresses three related questions: (a) What educational and transitional services does IDEIA require schools to offer students in juvenile correctional facilities in the United States? (b) How are parents involved with the education and rehabilitation of their children with disabilities in correctional confinement? (c) What are the challenges associated with parental involvement and transition to and from incarceration for students with disabilities?