Can patient-therapist moment-by-moment transactions uncover contrary treatment outcomes? The current study answers this question by analyzing the transcripts from eight therapy sessions of 20 patients each, for a total of 160 sessions and nearly 30,000 units of analysis. Patients were matched into ten pairs, each having the same diagnosis and the same clinician but with opposite treatment results: Ten patients were classified as responders (i.e., good-outcome patients) and as many as nonresponders (i.e., poor-outcome patients). Patient and therapist behaviors were coded using the Structural Analysis of Social Behavior (SASB) model. Overall, patients and therapists engaged in complementary relational patterns: Good-outcome patients tended to adopt loving and protecting interaction styles, similarly, therapists treating good-outcome cases employed protection and self-disclosure behaviors. In contrast, poor-outcome patients tried to interpersonally separate from the therapist, and both—patients and therapists alike—exhibited attacking and recoiling behaviors. However, when taking a closer look, i) separation appeared to be disruptive per se, that is, beyond any evidenced interpersonal asymmetry; ii) self-disclosure on the therapist side turned out to be supportive of therapeutic complementarity; iii) when facing failure, highly experienced therapists seemed to indulge into noncomplementary or even hostile behaviors. Findings confirm that the target of the patient- therapist transferential transactions should be distinguished from transactions regarding other people or other life circumstances in order to avoid misleading interpretation of data and, consequently, conducting therapy based on misleading grounds.