Throughout the eighteenth century, the Spanish Bourbon Crown ordered a series of reforms- the Bourbon Reforms -intended to strengthen Spains 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 Spains loss of Florida and, more broadly, the loss of its other New World colonies - the failure of the Bourbon Reforms - through the militias 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 militias 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.