Section 504 coordinators, special educators, and administrators at the secondary level are critical to student success in postsecondary education based on the transition planning and programming they provide. Despite the hard work and effort put into transition planning and programming, Best Colleges (March 2023) reported that the six-year graduation rate of students with disabilities at four-year colleges is 49.5%, compared to roughly 68% for students without disabilities. The graduation gap may be influenced by the fact that students with disabilities often need the same educational supports as they did in secondary school. However, in higher education, students (a) are required to self-request services and (b) supports may differ under Section 504 of the Rehabilitation Act (504) and the Americans with Disability Act of 1990 (ADA) (Hong, 2015). This presentation explores transition planning as one factor that negatively affects the completion rate disparity (Office of Civil Rights, 2011). At times, transition planning does not adequately prepare students for postsecondary education regarding how Section 504 and ADA are applied and impact the types of accommodations students receive in postsecondary schools. We will discuss the differences in how Section 504 is implemented in secondary and postsecondary schools, and what constitutes a “reasonable” accommodation. The expectations postsecondary institutions have of students regarding independence, self-advocacy, and meeting the requirements of a course will also be discussed. Finally, we will provide suggestions for a “Transition Toolbox” for secondary educators and administrators to assist with transition planning with their students.