Black and Latino adolescent boys and young men from low-income communities face numerous perceived and actual barriers to achieving their postsecondary educational goals. To advocate for more precise interventions, this study investigated how black and Latino eleventh grade boys' college ambitions were shaped by their school's college-going culture, racial stereotyping, and their families' economic marginalization. Drawing from social cognitive theory, the author examined the boys' college-going dilemmas as internal (e.g., participants' self-assessments of their academic [un]preparedness and [un]ease about making new friends) and external (e.g., concerns about affording college, given limited financial resources and familial responsibilities).