Yes, that great maybe-existed, maybe-didn't simultaneous example both human ingenuity and total stupidity, the Trojan Horse, got its day in the sun way back on April 24, 1184BC. Wired has a great post on how the TH, while perhaps historically dubious, has become a cultural touchstone. There's also something in there about network security, but I kind of glossed over it. Some lessons:
Cassandra was a Trojan prophet who warned against accepting the gift. Today, her name means a person whose warnings are ignored. Another skeptic was Laocoon, who Virgil says first uttered, "Beware of Greeks bearing gifts."
I'm a bit dubious of the last one. I lived with a Greek roommate for a while, and his gifts were always thoughtful and of high quality, rarely containing hidden soldiers who waited until night before sacking my bedroom. I also wonder why 'Trojan' became a brand name for condoms. As the Horse-full-of-Greeks episode demonstrates, Trojans aren't particularly adept at keeping anything out of anything else. I'll leave it up to you to draw the obvious analogy.