Although college enrollment rates have expanded over the last several decades, low-income students and students of color continue to face formidable barriers as they seek entry into higher education. While the existence of these barriers are often viewed as macro-level roadblocks that are largely systemic, much of the literature around access to higher education continues to use comprehensive college choice models as a way to explain how students as individuals come to arrive at a particular decision about whether and where to enroll in postsecondary education (Hossler & Gallagher, 1987; Hossler & Stage, 1992; Hossler, Smith & Vesper, 1999). These models are only partially useful in examining the college decision-making process because they assume that all students have access to the same information. Underrepresented students bring with them experiences that are situated in their family, school, community, and cultural contexts. This study unpacks the complexity of the college choice process by situating one's family background and school context in the broader system of social inequality (Bergerson, 2010). This longitudinal qualitative multi-site case study presents narratives of eight high school students attending two high schools in one urban school district. Participants were followed for four years, where they described their college aspirations, actions, and decisions from the ninth grade until the end of their senior year in grade twelve. Pierre Bourdieu's social reproduction theory (1979/1984) was used as a theoretical framework to investigate how family background and school selectivity shaped students' college aspirations and choice. The findings offer two contrasting pathways relative to the college choice process. The first pathway to college was interrupted in some way by the students' school, family, community, or a lack of support. In the second pathway, college choice was a relatively uninterrupted decision about where to attend college rather than if they should attend. Findings call for a reframing of "college choice" by introducing "college social conditioning", a new lens which places one's structural environment at the center of decision-making. Implications suggest the need for more intentional interventions and strategies that are aimed at challenging institutions, especially larger systemic barriers of social inequality. [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.]