Somalia today stands as one of the most persistent contexts of child soldier recruitment and use globally. The emergence of the Islamic militant group Al Shabaab has intensified fears about the insecurity of – and threat posed by – children as agents of war in Somalia. This article contextualises Al-Shabaab’s recruitment and use of children within its specific historical, political and cultural dimensions, challenging the emphasis in terrorism studies on the ‘unique’ phenomenon of children in extremist groups and relating the pathways of youth in Al-Shabaab with wider trends in criminality and violence, including piracy. This research responds to the need for deeper analysis of Somalia’s history of youth mobilisation that considers the specific constructions of age and masculinity that have influenced the participation of young people in diverse armed groups.