This session will cover the foundations DevSecOps and the application of Chaos Engineering for Cyber Security. We will cover how the craft has evolved by sharing some lessons learned driving digital transformation at the largest healthcare company in the world, UnitedHealth Group. During the session we will talk about DevSecOps, Rugged DevOps, Open Source, and how we pioneered the application of Chaos Engineering to Cyber Security. We will cover how DevSecOps and Security Chaos Engineering allows for teams to proactively experiment on recurring failure patterns in order to derive new information about underlying problems that were previously unknown. The use of Chaos Engineering techniques in DevSecOps pipelines, allows incident response and engineering teams to derive new information about the state of security within the system that was previously unknown. As far as we know Chaos Engineering is one of the only proactive mechanisms for detecting systemic availability and security failures before they manifest into outages, incidents, and breaches. In other words, Security focused Chaos Engineering allows teams to proactively, safely discover system weakness before they disrupt business outcomes.