The best security measures in the world, even the seemingly flawless and fool-proof of systems, can be beaten by the simplest of things: the failing to enforce it.
In Little Brother by Cory Doctorow, there was a point in which Marcus received an email from some followers who were caught jamming by some cops. However, after waiting to be interrogated in one a prison truck, they were released after a new shift of cops decided that they had "better things to do than bother [them] with more questions."
Isn't this so telling of our relationship with technology? It is the whole "Technology is only as good as the person using it" argument all over again. If someone somewhere along the chain of command decides that he/she doesn't care, the whole system goes down the drains.
This is also evident in other historical cryptographic events as well. The Enigma machine was cracked partially due to the fact that cryptographers got lazy. They had predictable language and sometimes even predictable keys (e.g. initials of loved ones). Without these, the Enigma could have been "uncrackable" for a much longer time.
This story from the book also interests me because it discusses human motivation in an almost real-world setting. Antoine de Saint-Exupery once said, "If you want to build a ship, don't drum up people to collect wood and don't assign them tasks and work, but rather teach them to long for the endless immensity of the sea." The DHS did not properly motivate their employees to ensure that they would follow through with their commands which led to failure in this situation. People will only go so far for so long when listening to orders before they give up. This can be due to any number of reasons. In one scene, when Marcus invited Ange over to use the XBox and chill for the evening, Ange points out one of these reasons and notes that Marcus's "only weapon is [his] ability to make [the DHS] look like morons." She points out that in order to derail the DHS, Marcus needs to undermine the motivation of the DHS to continue what they were doing.