[Python] How to programmatically auto-detach WinDbg from a process after it exits (in headless...

We have an internal test automation tool that runs tests on VMs. For each test: -A new process is spawned. -After execution, it ends with sys.exit(return_code) to trigger the next test.

Recently, I integrated WinDbg to attach automatically to the test process at start, in order to catch crashes during regressions and this helped identify some issues. However, I'm facing a blocker: When the test process exits gracefully, WinDbg remains attached. Since the next test is triggered via sys.exit(...), it won't start until WinDbg detaches manually. This means I need to log into the VM and run .detach manually every time which defeats the purpose of automation.

What I’ve Tried: pywin32, pyautogui, and pywinauto to send .detach to the WinDbg GUI.

Problem: These tools require an active desktop session and do not work on headless VMs.

I also attempted scripting through .scriptload and .shell inside WinDbg, but found no reliable hook to auto-detach on process exit.

Goal: We want to permanently integrate WinDbg for crash capture in our automation flow. So we need a headless-compatible method to ensure WinDbg: -Attaches to the test process automatically at start (this already works). -Detaches automatically once the test process exits (this is the missing piece).

Key Constraints: -No UI automation (no RDP access or active user session). -Must work on isolated VMs in CI/test infrastructure.

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