Utilizing longitudinal data gathered in a public safety-net hospital, the present study explored the relationships between patient attachment and therapist countertransference across concurrent three-month intervals. The aim of the study was to examine if changes in patient-rated attachment were associated with changes in therapist-rated countertransference. Patients completed a self-report attachment inventory (Experiences in Close Relationships- Short Form) and therapists completed self-report countertransference measures (Therapist Response Questionnaire). An analysis of 60 therapy dyads (nested within 21 therapists) revealed that higher patient attachment anxiety three months into treatment was significantly associated with increased helplessness/inadequacy countertransference from three to six months. Additionally, results from our analysis using multilevel-modeling revealed that increases in anxious attachment from three months to six months were associated with concurrent decreases in therapist reports of disengagement countertransference over the same time interval. Taken together these findings better illuminate the relationship between patient attachment anxiety and therapist countertransference over time. The results of this study denote the importance of attuning to these constructs carrying implications for both theory and practice.