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The 2 treatments, in this case comparison study, are strategically chosen to illustrate one of many or a result from a randomized controlled study on the long-term effect of transference work (Høglend et al., 2006). Namely, the interaction between transference work, therapists' self-reported parental countertransference, and patients' personality pathology that were reported by Dahl et al. (2014). Their findings indicated that transference work in the context of relatively strong parental countertransference was positive for patients meeting criteria for high levels of personality pathology but negative for patients with low levels of personality pathology. To shed light on these results, 2 patients with different levels of personality pathology and divergent long-term results, treated by the same therapist who reported high levels of parental feelings while using transference work in this time-limited dynamic psychotherapy were chosen. Victor and Tim's treatments fulfilled these conditions and will be presented using interviews and questionnaires from before, during, and after therapy, until 3 years follow-up. The therapeutic interaction is examined with finer grained process analyses, and session transcripts are included to demonstrate how transference work is delivered in this study. This article illustrates treatments behind the statistical analysis. More explicitly it exemplifies how parental countertransference may color transference work for better or worse due to interactions between therapist and patient. The self-reported parental countertransference may be seen as an empathic response leading to new relational experiences and long-term positive change or an enactment leading to repetitions of earlier interpersonal patterns and no change in the long run.