Sorry, I haven't had a chance to set up a test machine with all the requirements.

It's almost certainly something in jpype, to be clear. Most likely it loads a DLL that hasn't been loaded yet, but does it under conditions where it won't load. Nothing we build as part of CPython should do anything interesting on load, at least nothing we can change/fix. So jpype will probably need an update to import something manually.

The only thing I can think of that changed along these lines in 3.9.0 is that we no longer LoadLibrary("api-ms-win-core-path-l1-1-0.dll") at startup (because we can assume that it's present now). That shouldn't matter at all unless jpype is doing some really weird stuff, as it's a system library with no code. But maybe it'll give someone a hint who knows the module better?