Jason Haddox, CISO and Chief Hacker at Buddotbot, shares his insights from a deep dive into modern breaches, sparked by a 2022 breach of his well-resourced and security-conscious organization by Lapsus$. Seeking to understand how such breaches could occur in prepared organizations, Jason engaged in one-on-one discussions with CISOs and meticulously analyzed breach notifications and articles. He presents the patterns he uncovered and shares both defensive and offensive strategies gleaned from his journey.