Abstract: A system and method for modeling viable threats and for evading deployed defenses on a network are described. As a defensive tool used for threat modeling, the system and method allows those responsible for the safety of their critical infrastructure and intellectual property to have a clear view of all failures in the security countermeasure products they have deployed. As an offensive tool used for defense evasion modeling, the system and method can be used to quickly ascertain a viable attack vector, select exploitation code, and cross-reference those exploits that will bypass every layer of countermeasure technologies to commercially- and publicly-accessible crimeware and security testing tools.