Objective: The purpose of this research is twofold: first, to investigate financially eligible Pell Grant community college students’ perceptions of barriers and enablers to student success, and second, to critique the financial aid satisfactory academic progress (SAP) criteria through a cross-case comparison of students who are meeting and are not meeting the academic requirements. Method: To complete this investigation, I conducted semistructured interviews with financially eligible Pell Grant community college students ( N = 62) who were meeting SAP ( n = 31) and who were not meeting SAP ( n = 31). To analyze the data, I drew on Brint and Karabel’s theory of democratization and diversion as well as Gutiérrez and Lewis’s conceptualization of empowerment theory, and I followed Braun and Clarke’s six-step iterative thematic approach. Results: Financially eligible Pell Grant community college students believe students need motivation, enough resources to meet their responsibilities, and cultural capital to succeed. Observable differences were identified between the two student groups in three areas: environmental responsibilities to resources ratios, cultural capital, and powerlessness. Contributions: Through this article, I created a platform for the voices of financially eligible Pell Grant community college students and their perceptions of barriers and enablers to student success. By conducting the cross-case analysis, the potentially arbitrary nature of the SAP criteria is apparent, despite the real consequences they create for students. This research contributes a long overdue qualitative critique of the SAP criteria, but additional research is warranted.