This manuscript presents the outcomes of a qualitative research investigation centered on the experiences of African American college students in terms of their preparation for high school, college, and careers within a Predominantly White Institution (PWI) situated in rural southeastern Wisconsin. At the time of this research, the comprehensive public university had an undergraduate enrollment of 10,196 students. Among these students, 82.1% self-identified as White, 7.8% as Hispanic or Latinx, 5.4% as African American, 3.2% as Asian or Southeast Asian, and 0.9% as American Indian or Alaskan Native. Using semi-structured interviews with willing student participants, the primary objectives of this study were twofold: (1) to recognize the sociocultural and institutional elements that influence the career trajectories of African American students attending the institution and (2) to effectively capture the educational and career viewpoints and voices of these students as they navigate the complex sociocultural and institutional landscape. Key findings from the research highlight the students’ perspectives on the substantial connections between their high school experiences, particularly those in and around a major urban center in the Midwest, and their subsequent college and career paths. Additionally, the study underscores the challenges these students encounter while navigating the physical and social spaces on a rural PWI campus. Recommendations are made for creating a more welcoming space for African American students and for supporting those engaged in the work.