While a number of studies have examined outcomes associated with early intervention programs that have a financial aid component, few have examined the experiences of student beneficiaries of those programs and the administrators charged with carrying out state mandates associated with the implementation of the programs. This gap in the literature exists for students and administrators at both the K-12 and higher education institution levels. This qualitative study reports findings from interviews and focus groups with 76 administrators and 150 students from colleges and universities in a Midwestern state that implemented a middle school-to-college access program. Findings highlight the disparity between institutional supports for students across the state, differential use of services provided, lack of clarity of financial support structures, and the resulting difficulties encountered by students in the program and the staff hired to administer the program.