In June 1607, a Tuscan fleet of about twenty ships and two thousand two hundred men attacked the fortress of Famagusta in Cyprus, with the aim of making it the base for the subsequent occupation of the whole island, which had been in Ottoman hands since 1570. The attack was a total failure: the Tuscan fleet, divided into two parts, did not meet as planned and the Greek inhabitants of the island, who according to Tuscan information should have rebelled, did not. Moreover, the Ottoman garrison was aware of the attack, which meant that the attempt at a surprise attack was in vain. It is clear that, excluding the logistical problem of the fleet meeting up, the enterprise’s lack of success was due to a total inadequacy of what we today would call “intelligence”. The information in Tuscans’ hands did not turn out to be completely correct and they were unable to keep the planned operation secret. However, by contrast, the Venetian intelligence was able to manage the information in its possession in a more cautious way, taking advantage of the situation effectively. Through this case study, the article aims to follow the scholarship on information-gathering in the Early Modern Mediterranean world, showing, once again, how important and extensive such networks were. The aim of this short study, which is based largely on archival documentation, is not to deal with the Tuscan raid on the island, but to identify the faults of the Tuscan “intelligence” that led to the misfortunate attack. Moreover, through the analysis of the documents, it is also possible to add some elements to the knowledge about the Tuscan Grand Duke’s Levantine network.