With multi-tier network archtectures, web services, custom applications, and heterogeneous server platform environments, keeping data and information assets secure is more difficult than ever. Coupled with this added complexity is the fact that criminal organizations have organized their hacking efforts; it is no longer just “script kiddies” trying to break into your network. Although there are many ways to secure systems and applications, the only way to truly know how secure you are is to test yourself. By performing penetration tests against your environment, you can actually replicate the types of actions that a malicious attacker would take, giving you a more accurate representation of your security posture at any given time. Although most penetration testing methods have traditionally been somewhat ad-hoc, that has changed in the last several years. Robust, repeatable testing methodologies now exist, and high quality commercial tools can be implemented to ensure that both testing parameters and results are high-quality and trustworthy