Schools along the Irish border operate on the cusp of two national education systems, two conflicting political affiliations, two opposing religious ideologies and, during the worst of the Troubles, two warring factions. While individual secondary schools have not formally operated in more than one national jurisdiction, their pupils frequently attend schools on one side of the border while living on the other, and in any case have been affected on a daily basis by the socioeconomic decline and political conflict going on around them. This chapter is essentially a case study of how school leadership is understood in this context, which includes the internal dimension of how the conflict impacts on students and on the curriculum; and the external dimension of how it influences parents and the local community. Some of the issues and challenges are distinctive, if sometimes subliminal, but generally the challenge is one of capability: a headship can only occur at a particular place at a particular time – we cannot choose when to live – and in conflict societies like Northern Ireland, schools deal on behalf of innocents with events that are outside their control.