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This paper reports a case study of a small, urban high school driven by a mission to fundamentally alter the inequities experienced by the low-income, racially and culturally diverse communities it serves. Drawing on observations, interviews, a survey, and documents, the analysis charts how the school embraced critical cariño, a form of care undertaken with historical and political consciousness of students’ lives. Four foci characterized this school’s enactment of critical cariño specifically: (a) a cultura of transformational resistance, (b) staff hiring guided by cultural connectedness, (c) robust community partnerships, and (d) critical pedagogy. This case demonstrates a school harnessing critical cariño at an institutional level to foster students’ academic and civic engagement, as well as community wellbeing.