This chapter discusses challenges faced by students with disabilities when transitioning to college and focuses on the complexities faced by both students and disability services administrators when seeking and providing support services. It describes strategies, recommendations, and implications for policy and practice to move, namely the institutional iceberg in order help students with any or multiple disabilities transition to college and gain the self-advocacy skills required for academic success. The chapter considers institutional iceberg as a metaphor for the slow-to-change higher education system, disengaged policymakers, and disconnected secondary and postsecondary education systems. It explores the role disability services administrators play in facilitating inclusion, which was rooted in the larger study and focused on how academically successful college students with physical disabilities transition to and navigate higher education from a strengths-based perspective of intersectionality. The chapter highlights the gaps in three areas of college access research: college knowledge, transition to college, and persistence to degree attainment.