You know you have it in you , that drive to do the ULTIMATE penetrationtest: one that is technically deep, hyper current, super relevant, clever,and really helps the target organization understand their business risk andradically improve their security posture. In short, you want to perform thebest penetration test of your life, your masterwork in the art of pentesting, something you can look back on with pride and say, \That. Was. TheOne." But, sadly, many penetration testers never realize this dream, due tolack of resources, time, capabilities, or even organization politicalbacking. But, as a thought experiment, what if you could, just once, conductthat dream penetration test? What would it look like? How would you approachit? How could you tell you had really given it your all? And, if such a testis impossible, why bother even thinking about it? In this talk, Ed Skoudisexplores these questions, focused on what we can learn from the hypotheticalultimate pen test that we can directly apply to our real, world pen teststoday. Loaded with specific tips, tricks, and strategies, this talk strivesto provide actionable advice for all security pros to up their game inproviding great penetration tests.