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This paper describes the evaluation, initial psychotherapy and subsequent psychoanalysis of an adolescent who presented with a severe psychosomatic process involving total body pain and profound fatigue. The author details the complex and multifaceted nature of the psychosomatic process as it unfolded in the treatment. The psychosomatic problem was not a single entity, but rather was comprised of diverse interwoven elements such as somatization, conversion on pre-oedipal and oedipal levels, conflicts over aggression, sexuality, identity, masochism, secondary gain, anaclitic depression, internalized self-other interactions with a depressed mother and transgenerational transmission of trauma. The author uses the case material to discuss technical approaches to problems that often arise in the analytic treatment of patients with complicated chronic pain and fatigue as the primary complaints. Such approaches include respecting the mind–body split as a primary defense, speaking the language of the body along with the language of the mind and developing the verbal sphere around the non-verbal symptoms. The author emphasizes that complicated chronic pain problems are common and can be helped by psychoanalysis as long as the unique and complex features are understood and reflected in the technical approach.