This paper is intended to promote discussion among professionals, policymakers, employers, parents, and individuals with disabilities concerning current and future challenges facing secondary education and transition services nationally. The issues identified and discussed should not, however, be viewed as inclusive of the full range of possible challenges needing to be addressed. This paper (1) presents findings from research identifying key issues influencing the implementation of federal legislation relating to transition services at state and local levels; (2) examines the impact of national organizations, government reports, policy groups, and the courts on secondary education and transition services; and (3) presents the major challenges that the Center must begin to address immediately. These challenges have broad implications for special education and its relationship with general education and community agencies and organizations responsible for supporting youth with disabilities as they make the transition from high school to postsecondary education, employment, and other aspects of adult life. [This paper is based, in part, on a synthesis of research funded by the U.S. Department of Education, Office of Special Education and Rehabilitative Services to the National Transition Network at the University of Minnesota and prepared by the National Center on Secondary Education and Transition for Youth with Disabilities.]