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Using theory from philosophy and from race studies, the author explores the countertransference confusions and enactments that can arise in working with trans and gender nonbinary patients. Case material is presented to explore in vivo the potential for enactments and toxic anxiety in the analyst in work with patients exploring or inhabiting new forms of desire and identity. Primitive states of anxiety and dysphoria may inhibit the analyst's capacities to allow freedom and reflection in cases of complex gender construction.