Corporate, government and military bodies focus significant resources to develop sophisticated and capable information-based systems. The concept of people and resources connected by a robust network capable of extremely high rates of information exchange is very attractive because it allows smaller groups to coordinate together and focus effects from geographically diverse locations. However, there is also a hidden danger that comes with such advanced technology. For example, in the case of the U.S. Military, clearly United States holds a technological advantage over our adversaries and that this advantage continues to expand. This technology gap has resulted in the emergence of potent asymmetrical warfare. All too often in science fiction movies, we see a small group of humans defeat a technologically superior alien race by striking at a hidden weakness that renders all of their advanced weapons useless, as a result of pervasive connectivity and interdependence. The analogy holds for any large network-centric enterprise, corporate or governmental. This paper addresses potential vulnerabilities of network centric warfare and focuses on specific technologies and methods that preempt this Achilles Heal scenario.