Developed a new CI debugging capability for the OctopusDeploy/Calamari repository, focusing on enhancing observability during automated builds. Introduced Open File Handle Logging, which leverages the lsof command-line tool to capture and log open file handles when specific error conditions are detected. This feature, implemented in C# with an emphasis on backend development and robust exception handling, enables rapid diagnosis of intermittent resource contention issues in CI environments. By surfacing detailed file handle information, the work improved diagnostics and reduced mean time to recovery for file-handle related failures, contributing to more reliable and maintainable continuous integration workflows.