This session explores how eighteenth-century racial understandings shaped British imperial and colonial Caribbean notions of allegiance, and how members of marginalized racial groups sought to challenge racially exclusionary concepts of national belonging. The roundtable focuses on three central questions, all addressed with reference to a cross section of marginalized racial groups in the colonial British Caribbean: Jews, slaves, enslaved African and Afro-Caribbean soldiers, and free people of African and mixed African and European ancestry. First, how did the British imperial state facilitate opportunities for the inclusion of marginalized racial groups as free subjects of the British monarchy and simultaneously increase racial tensions in the colonial Caribbean? Second, to what extent did demonstrated loyalty to the Crown and the white colonial order—though military service, for example—alter British imperial or colonial attitudes toward members of marginalized racial groups? How did more expansive notions of allegiance and subject status in eighteenth- and early nineteenth-century Britain clash with racialized definitions of belonging prevalent in the Caribbean slave colonies? Third, to what extent did the efforts of individuals or groups who spoke out against their subjugation on the basis of claims of loyalty to the Crown influence racial attitudes and imperial policy in Britain? Focusing on debates regarding Jewish claims to the franchise in Jamaica, Dana Rabin will address how metropolitan imperial policy collided with colonial notions of race, belonging, and allegiance. Maria Alessandra Bollettino will discuss the difficulties that lay in store for slaves who obtained freedom by cooperating with the colonial government, while Matthew Dziennik will consider how efforts to educate the soldiers who comprised the West India regiments aligned with broader attempts by the British state to “civilize” othered peoples through military service. Brooke Newman will address the rhetorical strategies deployed by the free descendants of slaves to claim equal rights with white subjects under the law.