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This study examines how disability accommodation policies support or hinder students with disabilities as they transition from K–12 to higher education. Grounded in the Social Model of Disability and Transition Theory, a document analysis was conducted of IEP/504 planning guidelines, district-level transition plans, and postsecondary disability services policies. The study identifies misalignments that disrupt continuity and equity in access. Findings indicate that while K–12 systems embed structured supports, higher education shifts responsibility to students, many of whom are unprepared to self-advocate. This research contributes to equity-focused policy development by highlighting barriers and proposing strategies for cross-sector collaboration. The findings underscore the need for reimagined, justice-oriented support systems that ensure inclusive, accessible transitions for all learners.