Installing Linux on a new PC isn’t that hard, right? How about replacing the operating system across a fleet of thousands of virtual machines across multiple clouds, and on-premises installations with major global enterprise customers relying on you to keep their infrastructure running 24x7? This was the challenge that faced Giant Swarm as they realized CoreOS Container Linux, on which their managed Kubernetes service was based, had been declared end of life — and decided to migrate to Flatcar Container Linux, with the help of Kinvolk. In this talk, we will explain the process Giant Swarm followed to decide on their migration strategy, the challenges of implementing it, and the lessons learned from the process.