Youth with developmental and psychiatric disabilities encounter significant vocational challenges, even when they receive supported employment services. We examined the barriers to employment for 280 transition-age youth with disabilities enrolled in supported employment in eight community rehabilitation centers. Employment team members identified each youth’s top three barriers to employment using a 21-item checklist. Lack of work experience, transportation problems, and program engagement issues represented common barriers for both youth with developmental disabilities (53, 36, and 25%) and youth with psychiatric disabilities (20, 33, and 26%). Additional common barriers among youth with developmental disabilities included cognitive problems (32%) and lack of social skills (23%) and among youth with psychiatric disabilities included poor control of psychiatric symptoms (23%). Despite receiving evidence-based employment services, youth with disabilities encounter many barriers to employment. Awareness of typical barriers for transition-age youth, including those specific to different disability groups, may help employment programs anticipate challenges and develop strategies that avoid these barriers and their effects on employment opportunities.