This study examined the learning trajectory of five US humanities teachers when navigating learning to teach the difficult history of school desegregation within a context of a six-month inquiry-based professional development. The research questions were: What do teachers frame as problems when teaching difficult histories? How do they reconceptualize and resolve the problems in a teacher community? The primary data included video recordings of small group discussions, where each teacher contributed lesson ideas for feedback from fellow teachers. Analysis drew from three modes of belonging, in conjunction with four dimensions of historical inquiry. The findings revealed that teachers often identified problems in teaching school desegregation by emphasizing issues related to teaching perspectives. However, through collaborative interactions with their colleagues, they were able to resolve these challenges. This was achieved by clarifying teaching goals, renegotiating the meanings of learning tasks, and selecting appropriate resources.