Freud, early in psychoanalytic history, modified hypnotic technique and recommended, in its stead, free association. This paper takes a close look at the theoretical foundations of that technique in light of theoretical developments over the past hundred plus years. It is argued that free association is similar to an asymptote, which is never quite reached. Moreover, it is argued that the direction to free associate is contraindicated in many, if not most, psychological disturbances. Guided association or avoidance of free association is sometimes required. For a limited group of patients, whose major ego functions (abstraction, integration, and reality testing), ego strengths (impulse control, affect tolerance, and containing primary process), object relations (capacities for empathy, trust, and closeness), and superego (shame/guilt) are intact, the direction to use the couch and attempt to free associate may still be quite useful. For most people who present for treatment, however, this approach is likely not beneficial. The complex arguments about the decision-making process regarding free association are discussed.