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The present case study aims to explore the unfolding of the working alliance in a case that ended with the client dropping out of psychotherapy, unilaterally cutting off her contact with the therapist. However, both quantitative and qualitative outcome assessments strongly suggested that. An analysis of session transcripts, the Client Change Interview, and the Interpersonal Process Recall interviews for three selected sessions was used to analyze the development of the working alliance and its contribution to the dropout. This case study illustrates how the working alliance is constructed differently during the different phases of the therapeutic process. Specifically, the fruitful problem-solving in the first part of psychotherapy helped the client to improve her functioning. Yet this intervention seemed to exhaust its potential over time, and later the dyad had trouble finding another useful mode of interaction due to the interpersonal context, leading to more serious ruptures and, eventually, to the dropout. The findings are discussed in terms of therapist responsiveness and of its role in the continuous negotiation of the working alliance.