This paper examines transference-countertransference convergences contributing to an impasse in the treatment of a patient with a history of being bullied and neglected. Issues of power and control saturate the patient’s intrapsychic and interpersonal worlds and impact the countertransference of an analytic candidate, eliciting shame, doubt, confusion, and alienation. To what extent do these feelings reflect empathic immersion in the patient’s world? To what extent are they byproducts of a budding analyst’s struggles with his own internal objects and with growing pains associated with choosing a theoretical orientation and developing one’s analytic voice in a pluralistic landscape? Clinical material is offered, tracing a clinical process in which the analyst’s varied attempts to engage with the patient culminate in a holding stance that is sometimes potentially defensive but ultimately facilitative.