Yeah, I’m not sure either here… I played around with pywin32 and GetDllDirectory() and it turns out it’s empty by default. I could dig deeper into finding what libraries are being chosen but I’ve exhausted my time budget for that now.
Considering the Monitor starts up it’s not a build-time or configuration problem as they’ll be loading the same Python interpreter. The fact that it’s happening outside of Nuke and Houdini also means it’s not part of their environment.
Just for fun, what happens if you clear PYTHONPATH before running deadlinecommand? We’re supposed to be ignoring that variable these days and using only our own location for everything.