Nothing obvious based on that description. I knocked up an example of what I think you’re describing just to reassure myself that some unknown macOS sandboxing gremlin isn’t to blame and it seems alright to me. Here’s the example <https://drive.google.com/file/d/1QOtQJpowNx-WaxV3syikkJuOmbS_FW5r/view?usp=sharing>, build with pyinstaller --windowed --add-data=help:help test.py. If you can’t get your one to work based on my one then you’ll probably have to share your one (or a simplified version of it).
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