As few studies document how teachers in urban contexts positively contribute to a college-going culture, this study adopts a counter-narrative approach, with a conceptual framework grounded in emotion and caring in teaching, to ask: How do teachers exhibit (com)passion in their efforts to support a college-going culture? Interviews with 12 teachers, supplemented by school documents, archival and observational data, and field notes from a qualitative case study at three urban high schools revealed how teachers maintained high expectations of students, exhibited high degrees of emotional understanding, and conveyed a strong commitment to students, their success, and postsecondary pursuits.