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This article deals with the psychological therapy of a patient incarcerated for repeated offenses. It illustrates the difficulties in treating this patient, who presented with massive addictive vulnerability related to significant narcissistic fragility, leading us to question these dimensions in terms of transference in an enclosed space, such as mirroring a psychopathological patient’s difficulties. First, we discuss the context of the therapeutic encounter. Then we focus on the impact of addiction on the transference, as well as links that this issue has with various traumatic events brought up at the time of the interviews. Finally, we focus in the light of this case on the specifics of the prison environment in the care of borderline patients.