Relations between militaries and masculinities—and hegemonic masculinity and the state—are well-established in the literature on gender and development. However, there is less research on how militarised masculinities relate to state governance strategies. This paper, based on qualitative research conducted in northern Uganda between 2014 and 2017, offers a gender analysis of youths participating in informal security arrangements. Civilian male youths accept poorly paid or unpaid work in the informal security sector in the hope of gaining access to livelihoods that will enable them to fulfil masculine ideal-types. However, this arrangement denies them the resources necessary to achieve the ideal-type of civilian masculinity, as well as the state’s military masculinity, which produces young men as subjects of the ruling regime. To reconfigure this relationship between civilian and militarised masculinities, one should understand informal security organisations in the context of alternative livelihood arrangements and take a long-term approach to the demilitarisation of the Ugandan state.