Purpose: The Workforce Innovation and Opportunity Act of 2014 mandates vocational rehabilitation (VR) counselors play a greater role in providing transition-related services for students and youth with disabilities, such as pre-employment activities and increased collaborative efforts with state and local education agencies and American Jobs Centers to improve employment outcomes. Method: We surveyed 538 VR counselors in 13 high performing State Vocational Rehabilitation Agencies to rate the importance of transition-related skills and their preparation to undertake these activities. Results: Overall, VR counselors rated the importance of all transition-related items highly, but rated their preparation to perform these practices significantly lower. Job exploration counseling was cited as the most important skill. In terms of preparation, working with employers was rated the lowest. In terms of barriers to serving youth, time and case management were cited most frequently. Implications for caseload specialization and preparation of VR counselors are discussed. Conclusion: The results of the study have implications for preparing VR counselors to comply with the WIOA mandates regarding transition services for students and youth with disabilities.