This article explores the colony of Santo Domingo just after it had passed from French back to Spanish hands in 1809. Although impoverished and at the very margins of the Caribbean plantation system, revolutionary winds were nonetheless buffeting the colony. Using the testimony of a failed 1810 conspiracy known as the “Italian Revolution”, the article explores the enduring inequalities present in Santo Domingo, the immediate influence of the Haiti to the west, and the beginnings of Latin American independence more generally. Whereas Spanish authorities and other Caribbean elites might have dismissed the colony as marginal to the political events, therefore, the conspiracy sheds light on its importance to subaltern travelers and migrants from neighboring islands. Finally, it shows the tremendous concrete and symbolic importance of the Haitian Revolution on the neighboring colony, complicating a historiography that often argues for conflict, and not interrelation, between the two sides of Hispaniola.