The Shift Left philosophy is a product of the Agile movement. Its practices encourage teams to test and validate software as early in the process as possible. It’s been shown that the earlier issues are found and addressed that overall quality, time to delivery, and project costs improve. As teams adopt Shift Left, one notable exception is often overlooked. That is deployment. Over the past decade, application deployment has steadily become more of a software effort. The argument can easily be made that validating application deployment, which has primarily become a software effort, is just as much a candidate for Shift Left as the application itself. With containerization continuing its rise on becoming the application deployment norm, the notion of a production-like system deployed as far left in the cycle as a developer’s workstation is a practical reality. In organizations that have adopted Kubernetes, each phase of the delivery pipeline is able to accurately replicate a production environment. In this session, we will examine the benefits and challenges of Shifting Left by building and validating Kubernetes-based deployments. Topics include replicating production environments starting with development workstations, strategies for maintaining deployment code alongside application source code, considerations for artifact registries and repositories, and tooling that can assist at each stage.