Background/Context: Facilitating dialogues about racial issues in higher education classroom settings continues to be a vexing problem facing postsecondary educators. In order for students to discuss race with their peers, they need skilled facilitators who are knowledgeable about racial issues and able to support students in these difficult dialogues. Yet previous research on difficult dialogues has largely focused on students' experiences in these dialogues and the outcomes they gain from participating in them with little knowledge about the roles of facilitators of these dialogues. Purpose: The purpose of the present study was to examine how postsecondary educators facilitate racial dialogues. Research Design: In this study, I employed case study methodology and conducted semistructured individual interviews with 22 participants, as well as examined participants' syllabi to see how they structured their courses. Findings: Findings reveal the practical strategies educators used to facilitate classroom-based racial dialogues, including utilizing group discussions, using various practical resources, developing ways for learners to apply racial concepts and theories to their lives, and providing ample space for students to debrief at the conclusion of the dialogues. Conclusions/Recommendations: Major conclusions and recommendations from this study include the importance of White educators facilitating these dialogues, educators conceiving of knowledge differently, the importance of paying attention to the institutional and classroom cultures for these dialogues, fostering collaborations between faculty and student affairs educators to enable students to grapple with racial issues in classroom and cocurricular settings, and connecting racial dialogues with other historical forms of oppression like sexism and classism.