Cloud Development Environments (CDEs) are critical for software development, offering a space where developers write and review code, but deciding between self-hosting or self-managing these environments can significantly affect operational efficiency. Gitpod's experience revealed that self-managed CDEs, while initially appealing for their control and integration, often lead to increased complexity, operational burden, and potential revenue loss, as seen when Gitpod discontinued its self-managed offering and laid off 28% of its workforce in early 2023. Instead, they transitioned to Gitpod Enterprise, a self-hosted but vendor-managed solution that balances control with reduced operational demands, simplifying updates and enhancing reliability. This model allows companies to maintain their infrastructure while offloading software management, providing a streamlined experience that meets stringent security and architectural standards. The Gitpod Enterprise architecture, developed in collaboration with early adopters, has been praised for its ease of installation and low overhead, significantly improving workspace startup times and operational efficiency compared to traditional self-managed setups.