In spring 2020 the COVID-19 pandemic collided with a national reckoning on racial injustice and ruptured our country's core. The effects of this collision necessitated something other than business as usual in school leadership: it called for the kind of courageous leadership rooted in equity and justice we describe in this paper. In this qualitative case study, we draw on nine months of data collected at a Title I middle school in the southeast to describe how the administration leaned into vulnerability and courageous leadership by naming and acknowledging uncomfortable realities and inviting collaborative engagement with the school community about these realities.