1This article illustrates a little boy’s journey from autistic-like symptoms into more adaptive ways of coping with trauma and separation. Drawing from the psychoanalytic literature on autism and trauma, it discusses how traumatic events in the first two years of life may cause a child to withdraw from social relationships and cause developmental delay. Using the case of a young child in intensive psychotherapy, the article considers his experience of separation and looming loss at an early age and also explores how the author’s concomitant bereavement impacted on the countertransference. In addition, the shifts in the young boy’s relationship to inanimate objects and particularly his attraction to rubber, is considered with reference to the psychoanalytic concepts of ‘autistic sensation’ and ‘transitional phenomena’. The author demonstrates how planning and preparing for the end of treatment was an essential part of the psychotherapy, helping the patient to develop resilience and to live through the experience of separation.