Worked on the python/cpython repository to enhance the reliability of Windows C Runtime installation, focusing on environments with non-updated Windows machines. Addressed a critical installer bug by introducing compatibility checks and improved error handling, which prevented install-time failures on older operating systems. Utilized C programming and XML to modify the installer logic, ensuring smoother first-run experiences for enterprise Python distributions. Validated the solution through CI/CD pipelines and Windows runners to confirm stability and prevent regressions. This work reduced post-installation issues and support requests, contributing to a more robust and maintainable Windows development and installer ecosystem for CPython.