This article presents the lessons that a team of evaluators learned during a study of a multicultural initiative in a large, Midwestern school district. During the evaluation process, three incidents brought the evaluators' multicultural best intentions into sharp focus. This article describes the evaluation's framework and process and then recasts the critical incidents as dilemmas, analyzing them to highlight the inherent challenges of culturally competent evaluation. It concludes with the implications of the evaluators' experience for evaluation practice and theory. As the authors of this article discovered, even the most deliberate attention to cultural issues does not guarantee a smooth ride. (Contains 5 tables.)