This article presents our collaboration as supervisee and supervisor at the Changing the Conversation Conference held in New York City, March 2019. We address racial enactments in supervisory dyads, the absence of institutional holding, and the barriers to speaking candidly about these experiences. We locate these struggles in race as a “forcefield,” in which experiences of difference collide in ways that can both transform and threaten cherished aspects of identity. In the process, we reflect on how legitimate concerns about confidentiality can, in this context, mask analysts’ desires to protect their access to normative privilege, institutional power, and facilitate avoidance of their own racialized shame.