This paper is about my experiences with psychoanalysis in Uruguay and Argentina during the upheaval of the 1960s and 1970s. It reflects the interweaving of personal, professional, and social factors at a given historical moment. During those years some psychoanalysts tried to expand the area of psychoanalysis to the larger community. This implied changes in praxis and training. The work was done in “operative groups” as a way of reaching a greater number of people. Some case examples show how this work was carried out. Eventually these changes were squelched by the military takeover in what became known as the “Dirty War.” All dissent was seen by the authorities as threatening to the social order and was eradicated with brutality and impunity. My experiences as participant/outsider during that time exemplified some of the personal adaptations and professional cost for advocating change.