With the U.S. government acknowledgement of the seriousness of cyber threats, particularly against its critical infrastructures, as well as the Department of Defense officially labeling cyberspace as a war fighting domain, the Cold War strategy of deterrence is being applied to the cyber domain. However, unlike the nuclear realm, cyber deterrence must incorporate a wide spectrum of potential adversaries of various skill, determination, and capability, ranging from individual actors to state run enterprises. What’s more, the very principles that achieved success in deterring the launch of nuclear weapons during the Cold War, namely the threat of severe retaliation, cannot be achieved in cyberspace, thus neutralizing the potential effectiveness of leveraging a similar strategy. Attribution challenges, the ability to respond quickly and effectively, and the ability to sustain a model of repeatability prove to be insurmountable in a domain where actors operate in obfuscation.