The rise in numbers of students with disabilities entering higher education necessitates stronger transition programs between high schools and postsecondary institutions. Under current transition plans, many students with disabilities leave high school without the self-advocacy skills they need to survive in college. Further, although some universities understand their legal obligations in serving post-secondary students with disabilities, the litigation suggests that more needs to be accomplished. It appears that in some cases both university professors and administrators lack full awareness of their legal obligations. This manuscript examines the challenges students with disabilities face in college, reviews relevant case law regarding the transition for students with disabilities from high school to higher education, and provides suggestions to assist high schools and universities in forging programs to better serve students with disabilities.