Recent calls from senior managers, human rights groups and academics continue to scrutinize the impact of solitary confinement. But much less attention has been paid to prisoners’ own motivations for segregation. By analysing interviews with 16 segregated men in a high-security prison (Category-A) in England, this article foregrounds motivation. The argument involves a detailed description of the complex, and sometimes contradictory, motives that may lead prisoners into seeking isolation. It further attempts to explore the relationship between segregation and the wider prison environment. For many prisoners, segregation has a ‘negative benefit’ or amounts to a form of ‘lesser evil’. Such phrasing hints at the difficult decisions that prisoners navigate and offers an alternative perspective on solitary confinement.