From the inception of the colonial enterprise on Hispaniola, Tainos and Africans challenged the body politic of coloniality by implementing resistance tactics to contest enslavement and assert their autonomy. My research uses a range of archival evidence and works of revisionist historians to examine the sustained rebellious activity by indigenous and Black rebels up to the end of the eighteenth century. Enslaved Tainos, ladinos, and bozales engaged in guerrilla warfare, plundered Spanish strongholds, established maroon enclaves, and constituted alternative identities and socio-political realities to assert their freedom. Hence, this essay demonstrates how these resistance tactics debilitated plantation slavery and consequently tempered the violent apparatus of control established by the Spanish colonial regime. Thus, this exercise intends to fill the gap in the understanding of a three century long generational saga of anti-colonial struggle that adeptly disrupted the matrix of colonial power. Keywords: Dominican Republic, Caribbean History, Slavery, Rebellion, Marronage, Tainos, and African