A rabbit trail is a simulated chain of unintentional leaks and links inevitably leading to something secret. It's designed to test the ability of open source intelligence (OSINT) operatives to find out information about their targets and their target's intended activities. It can also be used to simulate the reconnaissance phase of a penetration test. During specific types of tests, it may be necessary to find out about individuals involved in the target company, and when assigned this task, few know what to do short of googling the individual's name. There's a great deal of skill that goes into effectively finding people on the Internet and uncovering their secrets (OkCupid is mild for the kind of people the world holds).

We're going to create a chain of social media accounts and open pages to lead the testers from one location to a completely different one that contains our key. We'll also set some ground rules for this kind of test. It's important that when...