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This case study of Mario Molina High (MHS), a small, urban high school in California examines how a dynamic interplay between organizational structures and instruction contributed to a schoolwide culture of engaged learning. The case documents students and staff deeply invested in learning as an activity that generated meaning, pleasure, and possibility. Academic engagement in and beyond classrooms entailed rigorous disciplinary challenges, language-rich communication, collaboration, culture, and context. Situated analyses demonstrate how teachers’ enactment of intellectual cariño (heartfelt care for students’ intellectual development) coupled with a schoolwide mission to immerse youth in transformative learning experiences enhanced low-SES Latino/a students’ schooling experiences, college aspirations and civic mindedness.