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Dynamic Interpersonal Therapy (DIT) is a brief psychodynamic therapy for depression, developed from the fundamental competences of evidence-based psychoanalytic/dynamic therapeutic methods. The 20-Day DIT training programme at the Anna Freud Centre in London is offered for clinicians who do not meet these psychoanalytic/dynamic competences. 28 therapists, each with three patients, underwent the 20-Day DIT training in 2019. The current study evaluated the 20-Day DIT training by investigating factors associated with the successful patient outcomes of this cohort. Reliable recovery and reliable improvement of patients was 69% and 90%, respectively. Quantitative analyses found that patients who have positive outcomes were likely to have lower baseline Patient Health Questionnaire-9 (PHQ-9) scores and lower patient complexity. A thematic analysis of the therapists’ perspectives suggested that the most important elements of DIT perceived to be associated with successful patient outcomes cluster around four superordinate themes: aspects of the DIT model/training, characteristics of the patient, aspects of the patient-therapist relationship, and characteristics of the therapist. The results suggest that the DIT protocol can be acquired by novice therapists in psychoanalytic/dynamic methods and offer insight into the factors that may be associated with successful outcomes.