Across society, the consistent influx of students enrolling in higher education institutions without a comparable increase in degree attainment has produced a heightened awareness and a desire to identify the factors related to influencing college success. This dissertation aims to develop a greater understanding of three potentially relevant factors and their respective influences in facilitating college success at the University of Arkansas. First, I evaluate the Student Talent Enrichment Program (STEP) Grant program, designed to fulfill low-income first-year students' financial needs and encourage their persistence on to their second year of college. Second, I study the effectiveness of the BounceBack Mentoring program; it paired peer-mentors with first-year students on academic probation with the goal of changing each student's academic trajectory. Third, I examine the role of non-cognitive skills, such as conscientiousness, and students' subjective expectations about their future performance in helping themselves reach their desired goals and in turn, perform beyond their expectations. In general, my findings suggest that access to the STEP grant program neither harms nor promotes short-run outcomes. I also find that the BounceBack Mentoring program show promise in helping undergraduates who are on academic probation improve their academic performance. In addition, I find that students who possess non-cognitive skills, such as conscientiousness and grit, are actively performing beyond expectations. Such findings are important because they highlight the complications, failures, and rewards of building support systems intended to promote, encourage and facilitate student success in a heavily diverse college student population. Overall, this dissertation and its findings lends itself to the fact that facilitating college success does not come from a single source, but likely is a combination of support programs, additional resources, and internal mindsets. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]