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This article draws on a qualitative study of 31 Millennial and Generation Z students to examine the meaning of teacher “caring” in a higher education context. Prior research clearly documents the importance of caring to student engagement, although much of that scholarship focuses on secondary schooling. Research also examines the changing demographics of higher education and new expectations brought to college classrooms by Millennials and others. In this article, we connect the existing research on caring and on generational differences to explore how traditional-aged undergraduates define caring and the degree to which that impacts their willingness to learn. Our findings indicate that students value approachability and relatability as traits in a caring professor; we also find that in-class pedagogical practices can dramatically demonstrate care or lack thereof. Our research suggests that the student success agenda in higher education must take in-class teaching practices seriously in order to impact students’ engagement and motivation to learn.