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A joint experience report from Fico and cosee of working together with development and operation teams to deliver a legacy on-premise application with high security requirements to the cloud using EKS. Imagine you have an on-premise application for financial transactions that additionally needs to be available in the cloud. As if this journey alone would not be a risky venture considering the security requirements, you also decide to use a cutting edge technology – EKS. In this talk, we present to you how we automated deployments for multiple customers, created parallel delivery streams for cloud and on-premise, each having different access patterns. Furthermore, we show how we dealt with encryption at rest and in-transit, automatic scaling, customers triggering long living workloads and a sufficient monitoring approach for the customer-support team.