Children and young people are growing up in contexts which are politically complex, often exacerbated by conflict or societal divisions. Yet, whilst it is generally accepted that schools have a role to play in helping young people understand their society, the subjects best placed to facilitate this are often afforded a low status in national curricula and controversial political issues are often avoided, or at best diluted to issues of ‘identity’, in classroom contexts. Arguably, as a result young people are not provided with the necessary tools to navigate the political terrain surrounding them, nor are they equipped to understand the political perspectives of ‘others’ in their local and global communities. It is suggested that placing greater emphasis on political complexity and controversy in the curriculum can develop young people’s capacity for ‘political generosity’ towards those with differing political perspectives. In particular, evidence from a controversial educational initiative in the Northern Ireland (‘From Prison to Peace’) is presented as one example of how this might be achieved. This initiative seeks to open discussion surrounding the complex political nature of Northern Ireland through engaging young people with the narratives and perspectives of former ‘paramilitary’ combatants in the conflict. Drawing on this example, broader features of ‘school readiness’ to engage with political complexity will be delineated and pedagogical principles for developing young people’s political generosity discussed.