Purple Teaming is the idea of using a Red Team exercise with clear training objectives for the Blue Team. Great exercises should not just be focused on testing a product, they should also test your active Blue Team members and their skills. But how does one start to think about a Purple Team exercise, how does one go about running one and what does it look like? In this talk we will explain what, why and how, to plan an effective purple team exercise and give some examples. Most enterprise networks are Windows heavy so examples will heavily lean on this. Testing Assumptions, gaps, blind spots is what being proactive is all about. This talk is both for the console folks and non-console folks.