Throughout the eighteenth century, the Spanish Bourbon Crown ordered a series of reforms– the Bourbon Reforms –intended to strengthen Spain’s position both in Iberia and its colonies. Among the institutions reformed was the Cuban Negro Militia, which then served in Spanish East Florida shortly before its annexation by the United States. This study has two aims: first, it explores the underlying causes of Spain’s loss of Florida and, more broadly, the loss of its other New World colonies – the failure of the Bourbon Reforms – through the militia’s eyes. It develops a new model with which to view the limitations of the reforms and the fall of Florida. This study also considers the militia’s tenure in Florida, particularly its desertions, as a microcosm of a larger breakdown in race relations taking place in the Spanish Caribbean, and argues that, far from being criminals, militia deserters had compelling reasons to flee.