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In a time of increasing political fragmentation, it is more important than ever that educators are equipped to facilitate dialogue across difference in their classrooms and schools. Using interview and artifact data from an online professional development course, this qualitative comparative case study examines twenty-seven educators’ navigation of dilemmas related to supporting dialogue across difference, and the extent to which they see this dilemma management as emotional, rational, and/or technical work. Emergent findings from early stages of data analysis suggest that the emotions of educators, their colleagues, and the students they serve may play a key role in their conceptualization and management of dilemmas involving dialogue across difference.