Bordin's (1979) theory suggests that therapist techniques that call for client introspection and self-observation will be more effective when the working alliance (WA) is stronger. Psychodynamic therapists use expressive techniques to elicit this introspection and self-observation. We examined whether therapists' use of expressive skills (e.g., encouraging expression of thoughts and feelings; helping clients understand the reasons behind their thoughts, feelings, and behaviors) when the WA is high, versus low, was related to client outcome in open-ended, psychodynamic treatment. Ten therapists rated the WA with their 47 clients, who rated their perceptions of helping skills, after 2,284 counseling sessions. Clients also completed the Outcome Rating Scale (ORS) in reference to the week following each session. We examined time-ordered relationships by creating lagged variables for WA (T-2) and therapist expressive skills (TES; T-1) and used these scores to predict ORS ratings (T) in a three-level Hierarchical Linear Modeling (HLM) analysis (sessions nested within clients, nested within therapists). Lagged WA (T-2) and expressive skills (T-1) were decomposed into between-therapist, within-therapist, and within-clients components. We found a 3-way interaction for within-therapist working alliance, within-client WA at T-2, and expressive skills at T-1 predicting ORS at T. When clients who had a weaker WA with their therapist than the therapists' other clients, had a session with a stronger WA than the client's usual WA, then more expressive skills in the next session was related to better psychological well-being in the subsequent session. Implications and future directions are discussed. (PsycInfo Database Record (c) 2022 APA, all rights reserved).