Over the past decade, school psychologists' role in facilitating the transition from high school to college for students with disabilities has become increasingly complex. Practitioners are faced with the difficult task of navigating the conspicuous disconnect between disability eligibility criteria at the secondary and postsecondary levels (NJCLD, 2007). In addition, the increasing popularity of alternative programs such as dual enrollment and virtual schooling presents a changing landscape when considering responsibilities for accommodations for students with diverse disabilities. This article is intended to explore emerging professional issues pertaining to documenting disability and accommodation needs for students transitioning to postsecondary education. Consideration is given to recent changes in federal law, guidelines by national organizations, and the shifting infrastructure of educational services in high school and college. Finally, specific accommodation recommendations are provided.