As human services professionals, we in higher education value helping people and often get personally invested in their stories. The people we serve, primarily students, face challenges in applying and paying for college, completing coursework and degrees, and finding employment after graduation. Along the way, college administrators strive to provide support through policy-driven programs and services. However, the special admission policy for students with felony convictions may be contradictory to the philosophy of higher education (Custer, 2013). Upon investigation, what I observed raised more questions than answers, and the essence of my confusion springs from a single college applicant's story. This article, a case study at one institution, is meant to spark reflection about the way admission offices treat the students who may need higher education the most: ex-offenders.