Patients receiving long-term dynamic psychotherapy often have both depression and personality disorders (PDs) and take medications concurrently. Our goal was to determine the extent of medication use in an outpatient sample and the relationships of medication use and PD status to diagnostic and symptom measures. Fifty-three patients (25 of whom were taking medications at intake) who entered a long-term psychodynamic psychotherapy study for the treatment of chronic or recurrent depression, anxiety, and/or PDs were followed up to 7 years. PD patients who received combined therapy showed significant improvement in functioning and distress, while those receiving only psychotherapy showed significant improvement in depression and distress. Non-PD patients receiving only psychotherapy showed significant improvement in functioning. Long-term dynamic psychotherapy was associated with improvement in symptoms and functioning for the sample as a whole. PD pathology and being on medications at intake acted as moderator variables: PD predicted a smaller effect size in depression and functioning, while medications predicted a smaller effect size in depression only.