Worked on the github-maccloud/runner-images repository to deliver a security-focused upgrade of OpenSSL to version 3.5.3 within the Windows 2025 build environment. The effort centered on dependency management and build system maintenance, using PowerShell to ensure a seamless integration with minimal disruption to existing CI pipelines. By prioritizing traceability through commit-based change management, the work enhanced both the security and compatibility of the build environment, allowing downstream teams to rely on updated cryptographic libraries. No major bugs were addressed during this period, as the focus remained on maintaining build stability and strengthening the overall security posture of Windows CI workflows.