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Jeremy D. Safran’s contributions to our understanding of the complexities of the therapeutic relationship, and its role in the process of patient change in psychotherapy, have been profound. In this paper, we briefly summarize the evolution of his thinking about the alliance and highlight how his ambivalence about this construct contributed to his seminal work delineating rupture resolution models, defined as negotiated intersubjective processes between patient and therapist that are the very essence of the therapeutic process for some patients. Responding to strains in the alliance throughout the rupture resolution process is critical and is an aspect of the treatment model that trainees find most challenging. A clinical example is included to illustrate how Jeremy’s attempts at metacommunicating about his experience with a frustrated patient initiated a productive shift in the process that also contributed to additional ruptures, requiring a simultaneous focus on the strained alliance.