This talk presents Workday’s journey towards deploying Istio Ingress to our Public Cloud environments. As we transferred our services from our legacy ingress to our new Istio ingress solution, a number of platform and application-layer issues surfaced. This talk presents how browser policy, HSTS, cookie stickiness, and headers can break applications, how we debugged those issues, and how we resolved them. Attendees can expect to learn some common and less common pitfalls of updating platform and infrastructure, the tools and techniques to triage them, and how they can impact the underlying applications.