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This study employs the voices of Black and Latino 11th grade boys from low-income communities, at one college preparatory U.S. public school to consider their multiple perceived barriers and challenges informing their college going process. Drawing from social cognitive theories and research on perceived barriers to college attendance, this proposed paper explores college going dilemmas as internal (e.g. participants’ self-assessments of their academic unpreparedness and unease about creating college networks) and external (e.g. concerns about affording college given familial responsibilities). Mitigating these dilemmas requires educators and scholars to creatively think about college going supports for vulnerable youths accessing college and succeeding on arrival.