With infrastructure and application automation we have gained the tools to change systems in the blink of an eye. However, with increasing size, complexity, and time, these components will inevitably challenge your expectations. This uncertainty will ultimately slow you down. This talk will introduce the workflow to gain back trust. We will cover the foundation of effective infrastructure tests and failure domains for isolation. Moreover, we will look into the management of divergent environments, from legacy systems to modern clouds. This talk will combine Delivery, InSpec, and Test-Kitchen in intensely mixed deployments.