The biggest challenge for any adoption in an enterprise is how to adapt new technology alongside generations of legacy applications and tools. Similar challenges exist while adopting Docker as containerization technology. This talk covers how to solve the challenge of Dockerizing hundreds of legacy apps across thousands of world wide developers, without transforming (imposing) the developers into overnight Docker experts, causing minimum overhead/touchpoints for the conversion and ensuring risk-free production migration. PayPal is in the middle of the journey, with the goal of containerizing all legacy applications to Docker containers. Containerization is the first step in the goal of moving to a dynamic cluster managed environment where any legacy application can live anywhere in the cluster.