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The intense espionage activity between the two most powerful political entities in the Mediterranean in the sixteenth century, Spain and the Ottoman Empire, has left the Spanish side of the large archives, relatively understudied for the most part. Some of these archives discussed here suggest various connections in the vast spy network in which, from the great Italian centers where it was established, the Spanish monarchy kept the expensive agents and messengers who seemed to be operating in enemy territory with apparent ease while reporting news of uncertain reliability. We can also see how the hunting for Turkish spies, in Sicily for example, became an obsession for the Spaniards.