In seeking to affirm queer identity, clinical social work practice and psychotherapy has potentially foreclosed consideration of how aspects of race inform gender experiences as well as desires for both cis and trans patients. This foreclosure may limit the complexity with which we understand both cis and trans subjectivities, particularly when whiteness is left uninterrogated as a structuring force in identity formation. The authors utilize composite clinical case vignettes and psychoanalytic thinking to bring attention to how colonial legacies are woven into experiences of gender and desire. Rather than seeking categorical affirmation, the authors propose resisting the drive toward clinical certainty and adopting a stance of uncertainty as a deliberate tactic for advancing decolonial practice. This stance potentially opens the space for patients and clinicians to explore potential colonial legacies embedded in all gender experiences.