Purpose: To examine the outcomes (rehabilitated vs. nonrehabilitated) of youth with disabilities (ages 14-22 years) participating in the transition program from a midwestern state. Method: Five years of vocational rehabilitation transition data (N = 6,252) were analyzed to determine what demographic and system-level factors were related to rehabilitated or nonrehabilitated outcomes. Results: Postsecondary and employment outcomes were predicted by race, gender, type of disability, office region, total number of services, and case expenditure. Hispanic youth had the highest percentage of rehabilitation; males fared significantly better than females and participants in small towns were significantly more likely to be rehabilitated than participants living in large urban areas. Conclusions: Based on the data findings, it was recommended that the vocational rehabilitation agency alters and updates its transition program. Strategies to help youth with disabilities achieve positive employment and postsecondary educational outcomes are discussed.