A protracted process of policy development has been underway in Jamaica to curtail the widespread incidence of informal settlements. Against the logic of emerging policy, this article aims to reconnect present-time unauthorised use of space to ancestral refusals of plantation land monopoly. Through ethnographic research and a reconsideration of historical texts, the article situates insecure tenure in a long history of conflict over land and livelihood-conflict that produces a boundary around the authorised use of space. That boundary is porous and mobile, the outcome of a palimpsest of colonial violence and its negation. This argument interrogates the gap between "landless" and "ownershipless", revealing both the role of incomplete dispossession in racialised social reproduction and the spatial practices through which Jamaicans "make life" even in the shadow of premature death.