Ed Skoudis' keynote at DerbyCon 2014 entitled "How to Give the Best Pen Test of Your Life" left Jeff hanging. He wanted to ask questions, get clarification, and most importantly suggest an alternative view of the purpose and goals of pen testing. This presentation is a follow-on or rebuttal to that presentation. The goal is to promote a conversation about pen testing that takes it to a higher level than ordinarily considered. Jeff will review, based on Skoudis' presentation, the key components of the "perfect" pen test, but take it farther to discuss the purpose, goals, and desired outcomes for pen testing. Join Jeff as he presents his notion of an ideal pen test, what it could/should be, how he came to this conclusion, and offer some direction for the future of pen testing.