Back in high school I spent some extracurricular time to build a river model as a Biology project. Basically a huge sandbox that could be elevated and have a water pump circulate/recycle water through it to simulate the effects of a river. To me, security is like building that sandbox and planning it all out, but once you turn that water on, it goes damn well wherever it wants to go, taking paths of least resistance using decisions you didn’t even know were possible. (Hence the usefulness of the model!)
People do the same thing in business and technology. Security puts down security measures (roadblocks, direction signs, suggestions, speed bumps, rules…), but people that want to do things a certain way will do them that way. The classic example is our current situation of using port 80/443 as universal tunneling ports. Security is blocking ports? Use the one they do open. Ops limits email attachments? Security filters out CC/PII in emailed attachments? Well, use your personal email account. Security/HR has web filtering? Use your smart phone and the guest wireless network to do your personal stuff.
And on, and on. It’s not so much a security problem as it is just a path of least resistance problem. Like driving through a parking lot outside the lines and risking not seeing the car to your side, rather than driving within the ‘rules.’
Which is funny, since we should also value creativity, outside-the-box thinking, innovation, and doing things new ways. Which is easily at odds with such rules.
This is why I’ve come to like Hoff’s blog name: Rational Survivability. If you/your business continue to survive, that’s really the goal, isn’t it? Every now and then, I think he knows what he’s talking about.