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In this article, we examine progress and challenges in designing, implementing, and evaluating culturally sensitive behavioral interventions by tailoring health communication to groups or individuals. After defining common tailoring constructs (i.e., culture, race, and ethnicity), cultural sensitivity, and cultural tailoring, we examine when it is useful to culturally tailor and address cultural sensitivity in health communication by group tailoring or individual tailoring and when tailoring health communication may not be necessary or appropriate for achieving behavior change. After reviewing selected approaches to cultural tailoring, we critique the quality of research in this domain with a focus on the internal validity of empirical findings. Then we explore the ways in which cultural sensitivity, group targeting, and individual tailoring have incorporated culture in health promotion and health communication. We conclude by articulating yet unanswered questions and suggesting future directions to move the field forward.