This practitioner-led dissertation used qualitative methods to explore the perspectives and lived experiences of historically underrepresented college students enrolled in higher education opportunity programs. This exploratory study engaged students of color, first-generation students, and students from low socioeconomic status (SES) backgrounds. Data were collected from students attending three selective, predominantly White, residential liberal arts colleges in New York State through an emic-focused practitioner research approach that employed semi-structured interviews, focus groups, document and archival review, and observational fieldnotes. This dissertation is grounded in theories of belonging, cultural capital, and social reproduction, and it is situated within the current context of higher education diversity, equity, and inclusion (DEI) programs at a polarizing sociopolitical moment in the United States. This study marks a departure from the corpus of research on college opportunity programs, which is primarily quantitative. This research connects students’ sense of belonging to their overall experience at selective liberal arts colleges, and to their specific experiences of financial, academic, and social support, program structure, recruitment, and outreach. Findings can be used to inform university-based understandings of program impact by those designing, implementing, and evaluating targeted opportunity programs. Belonging emerged as an exponentializing impact factor shaping students’ lived experiences and perspectives on the efficacy and quality of their programs.