The encounter between a patient and her surgeon is unique for several reasons. The surgeon inflicts pain upon a patient for the patient’s own good. An operative intervention is irreducibly personal, such that the decisions about and performance of operations are inseparable from the idiosyncrasies of the individual surgeon. Furthermore, there is a chasm of knowledge between the patient and surgeon that is difficult to cross. Hence, training in the discipline of surgery includes the inculcation of certain virtues and practices to safeguard against abuses of this relationship and to make sure that the best interests of the patient are prioritized. The stories in this issue are evidence that in contemporary practice this is not quite enough, as surgeons reflect on instances they felt were ethically challenging. Common themes include the difficulty in communicating surgical uncertainty, patient–surgeon relationships, ethical issues in surgical training, and the impact of the technological imperative on caring for dying patients.