This paper examines the new “interactive” theorizing in the context of a fundamental paradox of psychoanalytic practice which has shaped theories of technique beginning with Freud. The paradox resides in the extent to which the work of psychoanalysis depends upon undependable capacities of the patient. This tension creates pressures on psychoanalytic practitioners which are often reflected in the creation of new theory in an effort to find “ways out” of the paradox. I propose that many of the significant historical shifts in our theories of technique, including the current “paradigm shift” emphasizing interactive aspects of psychoanalysis, have been surprisingly kindred efforts at “solving” the problems of this paradox.