Given the disproportional rates of youth with disabilities who are being incarcerated, it is important to ensure they are receiving a free appropriate public education (FAPE) as defined under the Individuals with Disabilities Act (IDEA). Based on the policies provided by the Office of Special Education Program (OSEP), we developed and implemented the Detained Youth Dear Colleague rubric to conduct a systematic content analysis of cases involving these youth. Using the Special Ed Connection® database, the authors identified 37 FAPE cases involving detained youth with disabilities between 1997 and 2018. Findings showed that litigation in this area has increased since the reauthorization of IDEA in 2004. The highest prevalence of cases included the components of Child Find and individualized education program documentation and involved students who had a behavior label. In addition, correlations existed between accountability and personnel qualifications and training, r(33) = 0.37, p < 0.05, and secondary transition planning, r(33) = 0.37, p < 0.05. Results of the study, implications for transition practitioners, and future directions are discussed.