The psychotherapy skills of psychiatry residents were assessed by using a structured-response supervisor inventory, the Supervisor Report (SR). Longitudinal data on the same resident across time showed a small but positive trend toward the acquisition of skill in doing psychodynamic psychotherapy. Mixed cross-sectional and longitudinal comparisons between ratings of the beginning residents and advanced residents demonstrated a significant, but small, increase in skill over the course of outpatient training. SR score changes also corroborated observational data on individual residents. While these findings suggest the utility of the SR in measuring changes in psychotherapy skill, the results must be considered in light of the relatively poor interrater reliability and only somewhat better test-retest reliability.