Due to mounting pressures to avoid offending individuals on the basis of demographic group membership, political correctness has begun to restrict student participation in our diversity courses. This restriction diminishes what can be learned from class dialogue, an important component of diversity instruction. This article offers a model of “political trans-correctness,” integrating discourse constructs of authenticity, sensitivity, and political correctness. When optimally functioning, a learning community will enter a “zone of understanding” where educators and students speak with candor and actively listen. Four key pedagogical tactics for adopting the model in the classroom are provided: building rapport, setting the ground rules, ensuring the right to remain anonymous, and maintaining the proper presence. Implications for operationalizing the model are discussed.