Whiteness, a sociopolitical racialized hierarchy, has been normalized, codified, and internalized by psychoanalysis and psychoanalytic spaces, including psychoanalytic institutes. In order for psychoanalysis and its practitioners to situate ourselves in society as relevant and useful, and mitigate racism and racist enactments, collusions with whiteness must be interrogated. Interrogating whiteness is an iterative process which presents an urgent need in the field of psychoanalysis. Linking theory with personal accounts, the author introduces a whiteness interrogation process. As a candidate in a psychoanalytic training institute, the author also describes how candidates and members can interrogate whiteness in psychoanalytic spaces, including theory, praxis, and institutions, while simultaneously engaging in personal whiteness disruption work.