Postsecondary education is quickly becoming a requirement for many flourishing and emerging career fields. Because of this, an increased focused on postsecondary enrollment and attainment has been seen in the education community, particularly in K-12 education systems. To that end, a large number of programs and organizations have begun to provide academic and college preparation assistance to these students in the form of academic advising, college coaching, and personal enrichment. Since the enactment of the Economic Opportunity Act of 1964, there has been a burgeoning population of such programs like the TRIO family. This article focuses on a group of graduating high school students who were participants in such a TRIO program. Their academic metrics as well as factors like demographics and TRIO program participation were examined, and although these results will not be a component of this work, they prompted additional questions concerning what could be done to provide more effective support for these students. Concurrently, suggestions for policy were provided and include an increased focus on individual student contact and mentoring relationships, as well as a stronger focus on academic preparation in line with the academic metrics measured in this study