Youth with disabilities are disproportionately represented in juvenile justice populations and their education-related outcomes and rates of high school graduation are poor. This study examined academic characteristics of youth with and without disabilities (N = 4,066) and reports on the education-related outcomes of these youth 3 years after release from juvenile justice facilities in Florida. During commitment, youth with disabilities earned high school credits and grade point averages on par with their peers without disabilities. The number of credits earned during commitment improved the likelihood that youth returned to school after release. However, only 44% of the school-age cohort returned to school after release. Students with emotional/behavioral disorders (EBD) and learning disabilities (LD) returned to school at higher rates but did not maintain gains made during commitment as they earned significantly fewer high school diplomas after return to school. Implications for transition practice are discussed.