This article will place escapes during the War of Independence into the context of both the revolution as a whole and the specific context of political imprisonment. It examines the reasons the IRA engaged in escapes and how they sought to effect them. It also investigates the impact escapes had on prison staff, how the actions of staff influenced the outcome of an escape attempt, and how escapes affected the staff–management relationship within the prison service. Escapes provided numerous benefits for the IRA and the nationalist cause, ranging from material to symbolic benefits, and they were often successful thanks to various facilitating factors. For prison staff, escapes built on the demoralising effect the presence of political prisoners generally had: they increased tensions and provoked confrontations within the prison service; exposed serious deficiencies in the ability of some staff; and exhibited the impossibility of enforcing safe and secure custody in the ameliorated and highly charged atmosphere of Irish prisons. This is the first research that analyses escapes during the War of Independence collectively, and establishes that escapes were more than simply another IRA operation and another failing of Dublin Castle’s response to the nationalist movement. Instead, escapes reflect broader themes and factors that overshadow the Irish revolution in general.