The end of a therapeutic relationship is experienced in a unique way by each patient and triggers complex feelings relating to early attachment issues, losses and traumas. It is an immense rupture: a process of attachment and separation, intimacy and loss that is an emotionally intense experience for both participants. This case illustration provides insight into the difficulties experienced during the process of forced termination in an analytic community‐training clinic. Following a 2‐year treatment, Peter, a patient who had been severely traumatized in youth, had to tolerate the pain of another loss; having to say goodbye to a therapist. We describe the therapist's initiation and engagement of the termination phase. A series of measurements of patient personality, therapist attachment, and change in alliance and outcomes provide information on the impact of Peter's history and the therapeutic relationship. Clinical illustrations highlight different parts of the decision‐making process in terms of the patient's sensitivity to loss, as well as the therapist's uncertainty around self‐disclosure. We suggest ways therapists may facilitate endings by addressing positive and negative feelings, providing a good‐enough attachment experience, and stimulating an internalization of the therapeutic relationship. Implications for clinical practice, research and supervision are discussed.