Kubernetes, despite its scalability and container orchestration capabilities, proved unsuitable for building development environments at Gitpod, as the company's journey revealed numerous challenges with resource management, security, and operational complexity. Development environments are inherently stateful, interactive, and unpredictable, necessitating unique infrastructure solutions that Kubernetes struggled to provide effectively. Experiments with micro-VMs offered potential benefits like enhanced security and resource isolation but introduced their own set of challenges. Consequently, Gitpod developed "Gitpod Flex," a new architecture that retains beneficial aspects of Kubernetes while prioritizing security and simplicity, enabling seamless integration with devcontainers and offering improved deployment flexibility. This new system, built with over six years of experience, aims to enhance the developer experience by reducing operational overhead and focusing on a zero-trust security model.