Health care in prison and particularly the health care of older prisoners are increasingly important topics due to the growth of the ageing prisoner population. The aim of this paper is to gain insight into the approaches used in the provision of equivalent health care to ageing prisoners and to confront the intuitive definition of equivalent care and the practical and ethical challenges that have been experienced by individuals working in this field. Forty interviews took place with experts working in the prison setting from three Western European countries to discover their views on prison health care. Experts indicated that the provision of equivalent care in prison is difficult mostly due to four factors: variability of care in different prisons, gatekeeper systems, lack of personnel, and delays in providing access. This lack of equivalence can be fixed by allocating adequate budgets and developing standards for health care in prison.