Annually, 40% to 60% of students who graduate high school and enroll in higher education do not exhibit the skills necessary to succeed in college-level work and will need remediation in mathematics or English (Jimenez et al., 2016). Successfully graduating from high school does not guarantee academic preparedness for college. To understand why a significant number of students are unprepared for college mathematics courses 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 cognitive ability and attitude toward mathematics. This qualitative instrumental case study, guided by Walberg's Psychological Theory of Educational Productivity, explored how five remedial mathematics college students at a four-year research institution in the mid-southwest perceive the role internal and external influences (aptitude, instruction, and environment) played in their academic achievement and attitudes toward the subject. I collected data through semi-structured interviews and focus groups and analyzed it using Creswell and Poth's (2018) data analysis spiral. I used multiple strategies to maintain validity and reliability and to enhance trustworthiness. First, I acknowledged my biases. Second, I used three strategies to ensure my research was neutral and valid: member checking, auditability, and peer review I found that while internal influences (e.g. ability, motivation, development) impacted student attitudes and journeys with mathematics, external influences (e.g. unengaging mathematics environment, negative experiences with mathematics teachers, quality of instruction) more heavily impacted their mathematics attitudes. External influences on mathematics attitude and journey outweighed the internal influences on mathematics attitude and journey, with 464 to 181 mentions or 72% to 28%, respectively. I presented implications and recommendations to five target audiences, including K-12 mathematics teachers, high school guidance counselors, school district administrators, college admissions counselors, and students. Key decision-makers must work collaboratively to find solutions to help reduce remediation rates for first-year college students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]