This dissertation focuses on how class background and institutional context shape students’ experiences of faculty mentorship, academic success strategies, and the relationship of college values and academic decision-making. In this comparative study, I draw from 68 interviews with working- and upper-middle-class students at a regional and flagship university to identify how institutional variation matters across moderately-selective public universities, the kind where the majority of four-year college students matriculate. Mentorship, often informal, is a resource most easily accessed by students with preexisting cultural capital—specifically, the knowledge that mentoring relationships are available and advantageous, and the skills for cross-status interaction with professors. In this way, mentorship can be understood as a mechanism of social reproduction: it is often critical for accessing additional resources, such as letters of recommendation, and connections to cocurricular opportunities (e.g., research assistantships). Academic success strategies, shaped by class- cultural norms for how to be a student and engage with authority figures, have unequal traction in college. I focus on the strategies students use to navigate common trouble-spots like a missed deadline or a disappointing grade, finding pronounced differences by class background. Finally, regardless of class background, students claimed to value college as an opportunity for personal development and well-roundedness; however, only working-class students chose their courses in a way that was consistent with these values, while upper-middle-class students were more instrumentalist, prioritizing a high GPA and career preparation. Institutional context mattered significantly in each case. Class differences in mentorship experiences, academic strategies and decision-making were much less pronounced at the regional university compared to the flagship. Working-class students at a regional university accessed mentoring relationships despite lacking start-up cultural capital, requested extensions despite lacking a sense of entitlement, and integrated goals of career preparation and personal growth when selecting classes. Upper-middle-class students at the regional university were less likely to contest their grades and did not choose courses to maximize their postgraduate competitiveness. I theorize the difference using organizational habitus, demonstrating how the particular structural and cultural characteristics of an institution combine to shape how class matters in college.