This article focuses on a small urban high school that developed a culture devoted to caring for their historically underserved students. Interviews with school founders, teachers, and alumni, as well as observations of classrooms and professional activities, revealed the high school attended to the affective needs of their students, which improved attendance and graduation rates, but often neglected to hold students to high academic standards, which led to future underperformance. The article concludes that, absent a fundamental belief that students are capable of high-quality work, other forms of caring are insufficient. (Contains 1 table.)