I really tried to use PyInstaller and Nuitka to deploy a Python command line [1] to Windows, Mac, and Linux users. We couldn't get around some system dependencies like OpenSSL needing to be available and not broken on user machines. We ended up re-writing the whole program from Python into Go [2].
Using Go solved so many long-tail bugs for us and just simplified the whole process of shipping code to user machines.
Here's the old but working build script that built both PyInstaller and Nuitka [3].
Much as I love Python, there certainly are some corners of the ecosystem like that which have issues. Zip file support is another one where it's fine for many common cases but you don't have to try very hard to hit some niggles. The thing is I don't know if that's particular to Python, or whether every language ecosystem has this but Python is so widely used more people hit these issues.
https://github.com/bazelbuild/starlark