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Students entering into higher education face a series of barriers, from administrative questions to financial problems to familial expectations. These factors could lead to a student not matriculating into higher education despite being willing and qualified. This paper aims to understand the challenges that a student faces. It utilizes an in-depth interviewing methodology of student facing staff members to understand their perspective on the barriers as well as potential policies to support students. Key themes that emerged from this research include the need for comprehensive support, the importance of integration with the K-12 system, and the role of institutional supports.