Private security work can be a brutal world of short-term contracts, exploitation, and under-regulation, where the imperative of profit is expected to trump collective notions of military brotherhood. Why then do so many demobilized soldiers turn to it as a vocation? While a rich body of work has revealed the vulnerabilities of demobilized military life, ethnographic investigations into how contractors experience and make sense of precarity are less common. Drawing on fieldwork with military veterans of European descent working and living in East Africa, this article argues that a central, yet underexplored, feature of contemporary security work is colonial nostalgia.