Worked on the Shopify/grpc repository to improve CI reliability and test stability for Python projects, focusing on Windows environments. Consolidated multiple tooling tests into a single Python script, streamlining the test phase and reducing maintenance overhead. Adjusted and later reverted Windows CI timeouts to address flakiness as the test suite expanded, demonstrating careful configuration management and responsiveness to evolving test needs. Used Python, Shell, and Batch scripting to automate and maintain CI/CD pipelines, ensuring more predictable feedback for developers. Documented changes thoroughly and coordinated with teams to validate compatibility, supporting safer releases and a more robust continuous integration process.