Youth with developmental disabilities are overrepresented in juvenile detention facilities when compared to juveniles without disabilities. In fact, juveniles with disabilities are four times more likely to be found in detention centers as they are to be found in public school settings (Griller Clark et al., 2011; Quinn et al., 2005). Recent efforts to improve the quality of care and services for these incarcerated juveniles have resulted in Los Angeles County’s adoption of new policies and procedures aimed at reducing recidivism for this vulnerable population. This dissertation study is situated within a comprehensive evaluation of these new policies and procedures. Employing case study methodology, and a framework of evidence-based practices from the field of special education (i.e., self-determination skills training, coordinated transition services, and disability-specific considerations), this project examined how a local detention facility implemented youths’ discharge plans, and facilitated the transition from detention back to the community for youth with developmental disabilities. Results showed that some elements of the evidence-based practices were present, but other vital elements were missing, such as a dedicated transition specialist, the integration of vocational training activities and self-determination skills training, and development of a meaningful feedback loop for staff who report feeling disconnected from the discharge planning process and implementation. Implications for research, practice, and systems change are discussed.