The goal of this paper is to explore arguments about the moral (in)appropriateness of counter-contempt as a justified moral and pedagogical response to racist contempt. Drawing on debates for and against contempt in moral philosophy, the paper suggests a "contextual" approach to contempt that pays attention to both the specifics of the concrete situation that agents are in when they are experiencing racist contempt and the context of the agents themselves, understood as the conceptual and affective tools that are available to them in order to discern and challenge the meaning of racist contempt. The paper discusses the moral and pedagogical dilemmas entailed in efforts to cultivate in the classroom (and beyond) the "right" kind of contempt--both as a pedagogical stance and as a political message--which does not backfire but instead inspires a productive engagement with racism.