Advances in S&T coupled with universal access to cyberspace have motivated both state and non-state sponsored actors to new levels in the development of novel and non-traditional modes of attack to coerce, disrupt, or overthrow competing groups, regimes, and governments using unconventional warfare strategies. Threat vectors, caused directly or indirectly are asymmetric, kinetic, and unconventional. Current national and defense strategies in Cyberspace are mostly reactive and defensive, rather than pro-active and offensive. The web-crawlers research innovative ways to target security breaches. Securing critical infrastructure requires a top tier protection. This chapter is focused on ways to understand and combat unconventional warfare in cyber-space from CIS standpoint. This is crucial in avoiding a potential Cyber 9/11. To provide accurate intelligence, surveillance, preparedness and interdiction of such combative postures, ongoing studies of the ways that advance S&T may be employed so as to remain aware, alert and proactive for any/all such contingencies of use, are advocated.