Not being prepared Whether it’s a product of laziness or just being on back to back gigs for weeks on end, at some point (usually now and again) a pentester goes on-site completely unprepared for the task at hand. Is it unprofessional? Yes, of course. Does it happen? Yes, of course. There are different forms of not being prepared, from simply not running the latest software updates through to the catastrophic situation of having pretty much zero knowledge of the test ahead and none of the equipment.