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Teaching about local, difficult history can center students, their communities, and civic action. However, teaching this kind of history through inquiry poses personal and professional challenges. This study explored secondary social studies teachers’ perceptions of these challenges as they considered and designed source-based instruction about the history of policing and activism in Detroit from 1954 to 1973. In this paper, we discuss three areas of tension that emerged: 1) Supporting structural critiques without dehumanizing individuals, 2) Challenging oppression while presenting and respecting multiple perspectives, and 3) Building bridges between difficult content and students’ experiences without fostering hopelessness. These findings highlight the need to incorporate teachers’ concerns when designing critical historical inquiries.