This chapter focuses on the rise of the contraband culture in Hispaniola in response to the economic challenges the island faced during the last decades of the sixteenth century. Smugglingexisted in some measure throughout the earlier years of the colony, but contraband as a widespread phenomenoninvolving all social groups of the island’s inhabitants appeared during the second half of the sixteenth century and had its origins in the lack of official trade and the search by local residents for alternatives to the Sevillian trade. By the early seventeenth century, contraband had become an intrinsic part of Hispaniola’s culture, and that of many other parts of the Spanish Caribbean. Thisraised the suspicions of some authorities and members of the clergy who feared the consequences that such close relations with foreign Protestant traders might have for the economic and spiritual life of the local residents. These concerned observers made no distinctions between French or English merchants. They were all seen as a threat to the economy of the island and the faith of its residents. This chapter also reveals the complete inability of Spanish bureaucracy to curve illicit trading.