Scholarship on St. Vincent during the Age of Revolutions has grappled with building a fuller narrative of the Black Caribs that explores their lives beyond the limitations of colonial warfare. Because the Caribs left little to no written documentation, scholars have had to rely on the biased accounts of British and French administrators to extract a wider field of possibilities. New methodologies have emerged over time that answer to these challenges of building narratives around groups that have been historically neglected in the Assembly and care of traditional archives. More recently, articles and histories of the Black Caribs have been written with a critical eye towards racialization, colonialism, and claims of genocide. However still, the Caribs are still historicized in relation to a framework of colonial warfare that considers declarations of success and defeat as finite, overlooking the potentials of a variety of experiences of the Black indigenous population, and others on the island. In this dissertation, I examine British colonial anxieties in the “interwar” periods and the points of departure from prominent logics of differentiation on the island. Specifically, I look at the political and social ruptures that occurred in between moments of official warfare and treaties, to determine what that meant for attempts at racialization and class structure for the rest of the island’s inhabitants. By exposing the colonial anxieties during times of “ceasefire,” and their panicked attempts at legislation to remedy both interior and exterior attack, I uncover a much more complex system of precarity, fear, and subversion in the British settlement. Through problematizing ideas of what it meant to win, lose, conquer, own, succeed, defeat, and petition, this work reveals the unstable modes of hierarchy that the British settlement desperately tried to enact. In this revealing, more possibilities for who the Black Caribs were, as well as other criminalized populations on the island, ultimately transpired. The research for this dissertation draws from a close reading of British Council Assembly meeting notes, property petitions, letters to parliament, newspapers, and governmental and military records from the National Archives in Kew, Britain. I examine British colonial insecurity and the Black Caribs during the final two decades of the eighteenth century, starting before the British claimed control of the island through the Treaty of Paris, up until the months following the end of the Second Carib war. I look at the condition of British militias, struggles for land holdings, precarious support from the metropole, prolonged legislation, and interior and exterior threats, and how these factors rendered frail the colonial settlement in St. Vincent. Throughout, I employ a method of “corroborated imagination” for Black Carib groups and individuals, that is grounded in evidence from primary documents, but also fills in the phantom context with details from secondary source materials and critical supposition. This dissertation argues that changing racial, gender, and class logics towards populations in St. Vincent were vital in erecting and maintaining the frail British settlement. These logics of differentiation and hierarchy were unstable, and constantly refused by the Black Caribs. These periods of social and political instability contribute towards my reframing of St. Vincent, “unmaking” the settlement and stripping it from its historicity of a unified and ideologically secure colonial state. Ultimately this dissertation explores how St. Vincent was a multi-space of possibility, not just for land surveyors and capitalists, but for Black indigenous people as well.