A community-based, multisite study using mixed methods examined the experiences and perspectives of Latino students and families in a low performing urban school district in New York State. This research project was spearheaded by a Latino Education Task Force which brought together multiple stakeholders in a collaborative effort to counteract high dropout rates and deficit thinking about Latino youth and their families. The findings reported here, drawn from a thematic analysis of data collected specifically from focus groups with parents, center on Latino fathers' perspectives and experiences. We utilized a conceptual framework of Latino family epistemology and alternative parental role theory to explore the role of Puerto Rican fathers in family-school engagement. Findings reveal that these fathers: (a) cultivate education as a family and community affair in order to promote school success; (b) critique dynamics within the parent-school--istrict system and advocate for their children; and (c) acknowledge their vulnerable positioning as fathers resisting racism and invisibility in schools and the larger community. Fathers understood middle-class forms of involvement as well as culture and power dynamics, suggesting their involvement was a form of agency--a pushing back against the system that made them distrustful in the first place. A common theme across the data sources is the idea of moving "contra la corriente" or going against the current. Our research highlights the need for collaboration and community action aimed at "adjusting the sails" as we move toward educational equity.