This qualitative case study examined five preservice social studies teachers (PSSTs) working in an urban teacher preparation program as they learned methods of critical historical inquiry (CHI). Moving from a critical multicultural citizenship education frame, CHI supports analysis of multiple perspectives and sources to construct equitable, justice-oriented understanding of the past on its own terms. Study results detail participant conceptual (mis)understandings with CHI, difficult histories, and historical perspective recognition limited their production of social studies curriculum aligned with critical multicultural citizenship education. Findings highlight the significance of preservice teacher epistemic cognition when learning CHI while also underscoring the importance of addressing preservice teacher historical positionality and political clarity when teaching CHI. In the absence of deeper conceptual understandings of CHI and a concomitant epistemic stance, PSSTs are unlikely to overcome institutional and political barriers or strategically navigate curricular constraints which increasingly block critical multicultural education in social studies classrooms.