This thesis examines the relationship between practices of citizenship and the challenges associated with the pursuit of, and threats to, security of individuals in contemporary Jamaica. This approach is accompanied by an unpacking of the ways in which people, occupying different spaces in Jamaican society, position themselves vis-a-vis the state. I argue that the security problem in Jamaica has to be understood in the context of a widening citizenship deficit, and the fact that there is a separate way, outside of the formal context of the state, of pursuing citizenship at the community level in what are referred to as garrison communities. This separate way has emerged in response to the failure of the Jamaican state to provide both citizenship and security to its most disadvantaged and disenfranchised members. The state, the legal rights it is expected to provide, and the universalistic discourses which form the basis of citizenship in the West, have not served as the primary means by which citizenship has been constituted for all Jamaicans. The character citizenship assumes is rooted in Jamaica's colonial past, and since the postcolonial period has been tied to a rather uneven and unequal developmental trajectory, influenced by colour/class relations, spatial formation, political culture and identity, as well as neoliberal policies and noticeable state failures. Through extralegal, dialectic, and contested practices, garrison communities have become essential sites for realising citizenship. The local practices that inform the social order of the garrisons are decidedly in conflict with, and contest, the state's legal-rational institutions, calling its legitimacy and the veracity of the social contract - derived from Rousseau - into question. The theme of the thesis is pursued through an in-depth, multi-sited study, carried out in three communities, that explore the particularities, the everyday security experiences and discourses of people occupying different places and spaces in Jamaican society, and through consideration of the security policies and perspectives of policy elites and policy managers.