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Successfully graduating from high school does not guarantee college readiness. Annually, 40% to 60% of students who graduate high school and enroll in higher education will need remediation in mathematics or English, meaning they do not exhibit the skills necessary to succeed in college-level work (Jimenez et al., 2016). To understand why so many students are unprepared for college mathematics upon enrollment, it is vital to understand their journey with mathematics leading up to needing remediation and the internal and external influencing factors that shape their perceived ability and attitude toward mathematics. This qualitative case study explores what internal and external factors are common among remedial mathematics students and how their self-perception of math ability and attitude affects their college readiness.