Debugger silently crashes as it seems

I have quite a journey already behind, so my apologies if I'm wrong here. It started with the debugger not working at all, but let me try to make it as short as possible.

1. observation: run file & debugger is silently crashing via remote tunnels connection (from macOS to Windows)
2. observation: run file & debugger is silently crashing when invoked locally (fully uninstalled VS Code as good as I could with deleting cache folders and registry entries)
3. partial solution: run file & debugger works again when invoked locally

now I am with a tunnel connection where I can run a file but when I try to debug the file (just with the debug play button) the debugger still crashes silently. at least that's now narrowed down somewhat.

all configs were working before (launch.json, venv, etc) and I'm using the latest VS Code (not insiders) everywhere.

How can I further debug this and bring helpful information?