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After recent update to 3.0 I noticed that winpty no longer works in standalone/onefile compiled version with Nuitka I found that some resource files (exe and/or dll) are not attached. Nuitka is supposed to handle data files used by dependencies, so it is most likely some misconfiguration of the package which doesn't communicate which files have to be included.
For others having the issue, the workaround is to manually add files. Example from using venv:
--include-data-files=./.venv/Lib/site-packages/winpty/*.dll=winpty/* `
--include-data-files=./.venv/Lib/site-packages/winpty/*.exe=winpty/* `
From my understanding, the package needs to specify files that have to be shipped with it to work and Nuitka just follows that. I guess @kayhayen can explain how that works a little better. I'm posting it as an issue with pywinpty because this most likely needs a fix in package configuration.
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