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Adolescent boys have the highest rates of disengagement and drop out from mental health services. Further, research suggests that when boys do enagage with services, they may value therapies that provide practical strategies rather than those that advocate the exploration of thoughts, feelings, and relationships. Research is therefore needed to gain a better understanding of teenage boys’ experiences of participating in such therapies. This qualitative study aimed to explore the therapeutic experiences of five male adolescents (aged 16 to 18 years) with moderate to severe depression, who engaged in Short-Term Psychoanalytic Psychotherapy (STPP) as part of a randomized controlled trial. Interpretative Phenomenological Analysis of semi-structured interviews was used for an in-depth and idiographic exploration of their experiences. Three themes were identified: ‘Pain in therapy for a worthwhile purpose’, ‘A relationship unlike others: creating a space for reflection’, and “Ending with ‘a little bit of relief and a little bit of hope’”. The findings offer insight into factors that made it possible for these adolescents to engage in and benefit from STPP – a positive therapeutic relationship and gaining self-understanding – and, aspects that hindered their engagement and led to premature endings. This knowledge could inform clinical practice with depressed adolescent boys.