The present study explored how student support service administrators responded to the observed transitional challenges of students with disabilities during a period of systemic imbalance. Administrators at four community colleges in Tennessee, responsible for the coordination of student disability services, participated in a multi-site case study. Analysis revealed students with disabilities had unrealized expectations of postsecondary education, sought the same individualized attention experienced in secondary school, and misunderstood administrative processes, especially those associated with securing accommodations, upon entering college. Although the transitional challenges were not unique, increased enrollments and an inadequate infrastructure added difficulty to administrators' ability to respond. Administrators sought opportunities for collaborative inclusion with stakeholders, internally and externally, to resolve the observed transitional challenges. Investigators suggest administrators initiate early transitional planning with students who complete a Promise scholarship application during their senior year of high school, utilize cross-trained temporary personnel during peak periods of inquiries, and project accommodation needs earlier to secure adequate resources and help students remain scholarship eligible.