The shift from life-prolonging and palliative care can be fraught with interpersonal complexities as patients face dilemmas around mortality and the dying process. Nurses can play a central role in managing these moments, often with a focus on promoting and enhancing communication around: the meaning of palliative care, the nature of futility and the dying process more broadly. These sites of nurse–patient communication can be highly charged and pose unique challenges to nurses including how to balance nursing perspectives versus those of other stakeholders including doctors. Here, drawing on interviews with nurses, we explore their accounts of communication about futility and the process of transitioning to palliative care. The interviews reveal nurses’ perspectives on the following: the art of conversing around futility and managing patient resistance, the influence of guilt and individual biographies in shaping communication, the importance of non-verbal and the informal in communication, the impact of conflicting organisational expectations on nurses and the process of learning to effectively communicate. We argue that these transitional moments articulate important, and at times problematic, aspects of contemporary nursing and nurse–medical relations.