This essay uses the concept of “Maroon in/securities” to refer to a number of creative practices of survival and a range of experiences and feelings that converge in the Maroon narrative. These two terms, when brought together, productively facilitate a dialogue between Maroon studies and security studies that might lead to keen interventions in both fields. The concept first allows us to talk about military praxis (and in particular, guerilla warfare) as a key part of the Maroon experience and narrative but also, at the same time, allows us to link this to strategies of survival. It discusses Maroon insecurity as a feeling forged in the unsettled intimacies of colonial relations. This feeling, in several ways, structured relations between Maroons and plantations and impacted the organization of daily life across both frontiers as well as the deployment of a range of surveillance assemblages. But even more than a feeling, Maroon insecurity might be said to describe an experience of precarity. This attention to these Maroon in/securities revises the grand narratives of marronage in heroic terms that have often been dominant in the cultural and popular imagination across a range of sites of representation. In attending to these different registers, the essay suggests that the concept allows us to think not only across Maroon studies and security studies but also across a range of experiences and relations that converge in the Maroon narrative and that resist and complicate easy categories and taxonomies.