This article investigates distances between therapists and their clients in their experience of the therapeutic alliance across the duration of the psychotherapeutic treatments in a naturalistic study. We looked at the working alliances from different vantage points—rupture, repair of ruptures, distances in the alliance impressions of both clients and therapists—and their correlation with treatment outcome. The only predictive variable of alliance ruptures was the inability of therapists to bond sufficiently with their clients regarding a sustainable working atmosphere, which could be identified through a continuous distant alliance rating by the therapists. Alliance ruptures in turn significantly predicted premature termination of treatments, whereas alliance ruptures per se did not necessarily predict treatment outcome. The paper discusses the possible role of the quality of therapists’ attachment styles as a potentially crucial variable in an effective working alliance in psychotherapy.