Explore the complexities and challenges of effective Red Teaming in this 19-minute conference talk from USENIX Enigma 2019. Delve into Aaron Grattafiori's insights on how proper Red Teaming goes beyond simple penetration testing, requiring a deep understanding of organizational functions, diverse technology stacks, and potential business risks. Learn why the "win and go home" model falls short and discover how adopting an adversarial perspective can critically inform detection, prevention, and response strategies. Gain valuable knowledge on the true goals of Red Teaming and its potential to significantly improve an organization's security posture.