Anti-Black racism is often overlooked in predominantly White spaces such as psychotherapy. This pervasive disregard and dehumanization reflects the perpetuation of ongoing racial trauma that can influence the psychological health of Black people seeking psychotherapy. Therapists, therefore, ought to be equipped and comfortable to have conversations about anti-Blackness and anti-Black racism in sessions, though evidence suggests they are often uncomfortable discussing race and racism in practice. To understand therapists' comfort when clients discuss anti-Black racism, we used a multiple case study approach to interview five practicing clinicians (two White, two Black, one biracial Asian and White). Within-case analysis elicited a sense of participants' personal experiences of being comfortable, and at times less so, when clients discussed having endured anti-Black racism. Cross-case analysis led to the identification of four themes: (a) Beyond Acknowledgment, (b) Drawing Personal Awareness into the Moment, (c) Engaging with One's Own Emotional Responses, and (d) I Am versus I Should: Proactive and Reactive Comfort. These findings are discussed within the scope of multicultural competence, multicultural orientation, and the value of cultural comfort when clients' discuss anti-Black racism. (PsycInfo Database Record (c) 2023 APA, all rights reserved).