CockroachDB initially faced significant challenges in running on Windows due to the reliance on Docker, which created complications for a distributed database requiring robust network communication and persistent storage. This approach led to numerous issues, such as misconfigured nodes and isolated clusters, prompting Cockroach Labs to prioritize developing a native Windows binary. By May, they successfully released an executable for Windows, simplifying the installation process despite it not being as rigorously tested as those for macOS and Linux. The transition required extensive modifications to accommodate Windows' unique system characteristics and dependencies, including overcoming platform incompatibilities and leveraging open-source tools through MSYS2. Despite simplifying the build process by switching from go build to GNU Make, the company faced ongoing challenges in managing dependencies and ensuring cross-platform compatibility. As a result, CockroachDB now offers a more user-friendly experience on Windows, although production deployments are discouraged.