I investigated how two U.S.-born Salvadoran eleventh grade boys formulated college-going mindsets at the nexus of family-based cultural influences, adolescent development, masculinity, and academic self-appraisals. With asset-based theories, findings show how immigrant families encouraged college going by shielding their sons from noneducational responsibilities and conveyed educational messages with words and deeds. Participants formulated mindsets by interpreting family- and school-based messaging and weighing college going against gender-based responsibilities. Implications for educational anthropologists and practitioners are provided.