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This paper explores ideas and practices that affect students with learning disabilities as they prepare for the transition into postsecondary education. Key points include how self-advocacy affects college preparation and navigation of the collegiate environment. Self-advocacy and learning disability literature is surveyed, finding evidence of highly resourced, well-informed high schools as a major tool in predicting college access for and preparing students with learning disabilities for the challenges of postsecondary education. The dearth of research about students who do not attend such high schools and therefore lack access to intentional self-advocacy preparation poses a threat to students with learning disabilities, and holds the potential to advance college access inequalities for this marginalized population.