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The therapeutic alliance is frequently cited as one of the most critically important common factors associated with therapeutic outcomes. While ruptures to the therapeutic alliance are inevitable in all treatments, more research is needed to investigate the contributions of both the psychotherapist and the patient in effectively repairing these ruptures in a manner that facilitates therapeutic progress. In appreciation of Sidney Blatt’s research demonstrating the powerful role that the therapeutic alliance plays in determining therapeutic outcomes, this exploratory report examines transcripts from the beginning, middle, and end phases of the analyses of three creative writers with a focus on the therapeutic alliance and therapeutic ruptures as related to transference-countertransference dynamics. The Collaborative Interactions Scale – Revised (CIS-R) was the coding system used to rate the analysands’ Direct Rupture Markers, Indirect Rupture Markers, Direct Collaborative Processes, and Indirect Collaborative Processes and the analysts’ Direct Collaborative Interventions, Indirect Collaborative Interventions, Rupture Interventions, and Form of Therapist Intervention. The key findings, which support the theoretical and empirical work of Blatt and colleagues, are as follows: (1) most of the analysand-analyst interactions were indirect, rather than direct, in nature; (2) the analyst’s used many supportive interventions in addition to more classic exploratory and expressive ones: (3) the presence of rupture markers was limited and the reflections of ruptures was primarily indirect and included affective withdrawal and verbal avoidance; and (4) analysands may make important and unique contributions to the rupture process. The empirical and clinical implications of the results are discussed.