The networked software systems we build are increasing in complexity every moment. Today the most successful builders and operators are embracing complexity through CI/CD, Chaos Engineering, and innovation in Incident Response. They realize that the adaptive world around us is advancing at such a breakneck speed, it is leaving our capacity to understand it in the dust. That humans and technology must race a gauntlet of automation surprises and collaboration challenges as a team, learning and improving along the way. This session showcases methods of deploying, running, and navigating complexity. It offers a practical view of how software systems can scale and remain robust to failure (like fallbacks or high availability), achieve highly reliable socio-technical operations (via runbooks and game days), and adapt to surprise through techniques of resilience engineering (graceful extensibility and building for adaptation).