Bruce Schneier presents a very cogent and convincing argument that "security awareness training" is a waste of money -- specifically, because the benefits of "security" are intangible, while the benefits of getting your work done are apparent.
To those who think that training users in security is a good idea, I want to ask: "Have you ever met an actual user?" They're not experts, and we can't expect them to become experts. The threats change constantly, the likelihood of failure is low, and there is enough complexity that it's hard for people to understand how to connect their behavior to eventual outcomes. So they turn to folk remedies that, while simple, don't really address the threats.
Even if we could invent an effective computer security training program, there's one last problem. HIV prevention training works because affecting what the average person does is valuable. Even if only half the population practices safe sex, those actions dramatically reduce the spread of HIV. But computer security is often only as strong as the weakest link. If four-fifths of company employees learn to choose better passwords, or not to click on dodgy links, one-fifth still get it wrong and the bad guys still get in. As long as we build systems that are vulnerable to the worst case, raising the average case won't make them more secure.
The whole concept of security awareness training demonstrates how the computer industry has failed. We should be designing systems that won't let users choose lousy passwords and don't care what links a user clicks on. We should be designing systems that conform to their folk beliefs of security, rather than forcing them to learn new ones. Microsoft has a great rule about system messages that require the user to make a decision. They should be NEAT: necessary, explained, actionable, and tested. That's how we should be designing security interfaces. And we should be spending money on security training for developers. These are people who can be taught expertise in a fast-changing environment, and this is a situation where raising the average behavior increases the security of the overall system.
I write books. My latest is a YA science fiction novel called Homeland (it's the sequel to Little Brother). More books: Rapture of the Nerds (a novel, with Charlie Stross); With a Little Help (short stories); and The Great Big Beautiful Tomorrow (novella and nonfic). I speak all over the place and I tweet and tumble, too.