This article suggests that opportunities exist to harness the potential of history and citizenship education with the processes of transition in developing programmes which support young people in exploring conflict and the challenges associated with attending to its legacy. Drawing on the experience of Northern Ireland, it is suggested that the narratives of those who have been involved directly as both combatants in conflict and latterly as agents of change in their communities provide unique opportunities for young people to reflect on these issues. By way of illustration, an account of one such initiative is presented: ‘From Prison to Peace: learning from the experience of political ex-prisoners’; a structured programme which invites young people to engage directly with loyalist and republican ex-combatants in the Northern Ireland conflict. The article suggests that such programmes have the potential to assist young people in exploring the complexity of conflict and the intricacies of transition. Furthermore it is suggested that the relationships which exist between these ex-combatants arguably can challenge sectarian perspectives and foster capacity for ‘political generosity’ towards those with opposing political aspirations.