Depressive disorders in adolescence pose unique challenges for assessment and treatment, particularly due to their high comorbidity with various personality disorders. Moreover, young depressed patients may elicit very intense and difficult-to-manage emotional responses in therapists (in this context, countertransference). This study aimed at empirically identifying specific personality disorders (or subtypes) among adolescents with depressive pathology and exploring distinct countertransference patterns emerging in their psychotherapy: 100 adolescents (58 with depressive disorders; 42 with other clinical conditions) were assessed by their respective clinicians (n=100) using the psychodiagnostic chart-adolescent of the Psychodynamic Diagnostic Manual (PDM) - second edition, and the therapist response questionnaire for adolescents. Results showed that depressed adolescent patients exhibited marked traits of four personality subtypes (i.e., depressive, anxious-avoidant, narcissistic, and borderline) characterized by different levels of mental functioning and personality organization. These subtypes were predictably related to specific clinicians' emotional responses, even when controlling for the intensity of depressive symptomatology. Patients with depressive or anxious-avoidant personality subtypes evoked more positive countertransference responses, whereas patients with narcissistic or borderline subtypes elicited strong and hard-to-face emotional responses in therapists. Consistent with the next edition of the PDM, the study emphasizes the importance of comprehensive psychodynamic assessment in the developmental age, which frames depressive disorders in the context of accurate emerging personality and mental functioning profiles. This approach, which also relies heavily on the clinician's subjective experience in therapy, provides crucial information on how to specifically tailor interventions that more effectively meet the needs of adolescents with these heterogeneous and complex clinical conditions.