Just as a good chess player thinks five moves ahead, a great penetration tester should be able to visualize their attack in order to compromise high-value targets. This presentation will explore how a penetration tester can learn to leverage attack chaining for maximum impact. A penetration test is supposed to be a simulation of a real-world attack. Real-world attackers do not use expensive automated tools or a checklist. Nor do they use a single technique or exploit to compromise a target. More commonly they combine several techniques, vulnerabilities, and exploits to create a “chained” attack that achieves a malicious goal. Chained attacks are far more complex and far more difficult to defend against. We want to explore how application vulnerabilities relate to one another and build a mind map that guides penetration testers through various attack scenarios. Prepare to be blown away on this roller coaster ride with real-world examples of massive compromises. If you are not a thrill seeker, this presentation may leave you a bit queasy.