In their first endeavors to colonize the Philippines the Spaniards needed local knowledge. It is true they had maps, most of them not very detailed. Sources of information were vital – but that information had to be in a language they could understand. Even Magellan had an interpreter when he “discovered” the Philippines in 1521. When Legazpi came to settle the islands in 1565, he used a number of different people as interpreters and guides. However, being a go-between could be highly dangerous, even deadly. From accounts in the Lilly Historia manuscript from about 1600 it is possible to supplement what is in the standard sources. I give an account of the roles of a number of interpreters and other informers in the Spanish period up to 1600. We know the names of a handful of them, such as Cabocotan, though the Spaniards usually only noted names of chiefs. Surprisingly, despite the Spaniards’ intolerance of Muslims, some were not just employed; they even had good relations with the invaders. I also provide more information about Juanes, a Mexican castaway on Samar from the Villalobos expedition, who promised to be very valuable but turned out to be somewhat of a disappointment at first. Of course, the Spaniards also had their own spies, for example Brother Gaspar Gómez, a Jesuit lay brother who was sent to spy on Maluku. As now, information is power.