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Although Blatt's two-polarity model of depression has suggested that patients' interpersonal styles may shape countertransference phenomena in psychotherapy, empirical research on this topic has remained scarce. This article provides an in-depth study of countertransference processes in clinical work with dependent (anaclitic) depressed patients using a qualitative methodology. Thematic analysis of narrative material of psychodynamic therapists discussing patient cases during supervision (n = 7) resulted in four recurrent themes: “empathy, compassion, and support,” “anxiety, feeling overwhelmed, and protection,” “frustration, irritation, and confrontation,” and “inadequacy, incompetence, and fatalism.” We found that these countertransference processes mainly revolved around perceived adaptive and maladaptive aspects of patients' relational functioning. Regarding clinical practice, our study suggests that therapists can use countertransference to determine in which position they are maneuvered by patients, although we caution against the exclusive use of subjectively informed data as a benchmark in the diagnostic and treatment process. We conclude that further in-depth research on countertransference and personality styles is needed to identify pitfalls in the treatment of depression.