Background/Context: Schools have attempted to address stratification in black and Latino students' access to higher education through extensive reform initiatives, including those focused on social supports. A crucial focus has been missing from these efforts, essential to improving the effectiveness of support mechanisms and understanding why they have been insufficient: how students experience these reforms. Purpose: How can the social context of schools keep underrepresented minority students on track to transition to college? This study investigates how students experience the social contexts of their schools in relation to their college ambitions, and the particular attributes of schools'social contexts that might positively affect their transition to four-year colleges. Research Design: Using a mixed-methods case study design, this three-year study examined students' educational pathways in a Chicago charter high school. Data collection methods included ethnographic fieldwork, interviews, and a longitudinal survey. Supplemental secondary data sources were utilized to contextualize the case study. Analysis: Interview transcripts and field notes were transcribed and coded to examine variation in students' experience of their social context and their college transition plans. To contextualize these findings, the author utilized descriptive, associative, and logistic regression techniques to analyze quantitative data from the case study survey and corresponding city and national datasets. Findings: The school's organization facilitated academic, social, and college preparatory support through structured relationships. Notiuithstanding, there was notable within-school variation in students' transitions to college. Students in this urban charter school often experienced multiple obstacles that interfered with the college ambitions they generally shared with their families and school peers. School regard is a mechanism identified in this study as central to students'transition success. Students'perceptions of their teachers'and their peers' regard for their capacity for educational success was associated with their persistence through the transition to college in the face of academic, socioeconomic, and other challenges. Conclusions/Recommendations: This study demonstrates the effort and engagement under-represented students expend in the effort to become college-ready, and the risk for burnout as a result of both academic and nonacademic hardships during their high school years. School regard may mitigate these effects. Mere expectations for college appear insufficient in the current access-for-all climate. Rather, it is important that students perceive value and esteem for their potential from school faculty and peers, sustaining their ambitions through the obstacles they encounter in high school and expect in college. [ABSTRACT FROM AUTHOR]