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Jeremy Safran has presented seminal and widely applicable clinical theory and research around the therapeutic alliance and ruptures in the alliance. We explore areas of agreement with and departure from some of Safran’s key conceptualizations on these topics, focusing on overlap and distinctions between two constructs theorized to be fundamentally significant elements of all therapeutic relationships: the working alliance and the real relationship. We share Safran’s view that the alliance centrally implicates an emotional bond between patient and therapist, as well as an agreement about the goals of treatment and the tasks needed to attain those goals. We depart from Safran, however, in his belief that the real relationship should be seen as part of the emotional bond of the working alliance. Instead, we argue that the real relationship and the working alliance (including the bond aspect of the alliance) are best viewed as highly interrelated but distinct aspects of the therapeutic relationship. In addition, a distinction is made between the working bond (part of the working alliance) and the personal bond (part of the real relationship). Hence, we examine the concept of rupture in the working alliance, and in the real relationship as well. The nature of ruptures is discussed, as well as what therapists can do to repair them. A more limited definition of ruptures than the broader conception that has evolved in recent years is proposed. It is suggested that, whereas ruptures in the working alliance generally can be repaired to the benefit of the work, ruptures in the real relationship are likely to be more damaging to the treatment.