Psychoanalysis, which at its core is a search for truth, stands in a subversive position vis-à-vis the contemporary therapeutic culture that places a premium on symptomatic “cure.” Nevertheless, analysts are vulnerable to succumbing to the internal and external pressures for the achievement of symptomatic improvement. In this communication we trace the evolution of Freud's thinking about the relationship between the aims of psychoanalysis and the alleviation of symptoms. We note that analysts today may recapitulate Freud's early struggles in their pursuit of symptom removal. We present an account of a clinical consultation in which the analytic pair were ensnared in an impasse that involved the analyst's preoccupation with the intransigence of one of the patient's symptoms. We suggest alternative ways of working with these clinical issues and offer some thoughts on how our own work as analysts and consultants to colleagues has been influenced by our understanding of what frequently occurs when the analyst becomes symptom-focused.