Racially and ethnically diverse youth with disabilities receiving Supplemental Security Income (SSI) benefits were randomly assigned to usual services, including available school and vocational rehabilitation (VR) transition services, or enhanced case management and transition services through the Wisconsin Promoting Readiness of Minors in SSI (PROMISE) federal demonstration grant. A hierarchical logistic regression analysis demonstrated increased age, being African American, having a psychiatric disability, and transition services predicted higher youth employment rates. However, enhanced PROMISE transition services were no longer significant in the presence of VR services, suggesting the effect of enhanced services was mediated by increasing engagement in VR. Limitations and implications are discussed regarding the relationship between school and state VR transition services and postsecondary competitive integrated employment outcomes.