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The present study examines relationships between patient attachment and therapist countertransference in a large, naturalistic, longitudinal study of psychodynamic psychotherapy in a safety-net hospital. This study explored patterns in the relationship between therapist countertransference and patient attachment in two ways: (a) by studying cross sectional associations between patient-reported attachment and therapist-reported countertransference at 3 months into treatment, and (b) by studying if changes in patient-reported attachment over the course of psychotherapy are associated with changes in therapist-reported countertransference. In a sample of 101 therapy dyads, patients completed self-report attachment domains and therapists completed self-report countertransference measures 3 months following initiation of psychotherapy. Results showed initial significant positive associations between patient-rated attachment anxiety and therapist-rated “parental/protective,” “special/overinvolved,” and “overwhelmed/disorganized” countertransference. A sample of 119 therapy dyads (these included dyads in which therapists and patients completed measures at any point in time) was analyzed using multilevel modeling. Results showed that initial patient-rated attachment anxiety was associated with decreases in therapist-rated parental/protective and special/overinvolved countertransference over time. Decreases in patient-rated attachment anxiety were associated with subsequent increases in therapist reports of feeling overwhelmed/disorganized. These findings provide a greater understanding of how attending to patient attachment and therapist countertransference together may cofacilitate treatment and improve patient outcomes.