Yes, codesigning remains a mystery to me too, and even worse since they
added 'notarizing' in Catalina. I've found an application which I use now
for code signing and packaging which takes a lot of pain out of the
process: App Wrapper (https://ohanaware.com/appwrapper/). It's not free,
but I find it very useful.

Even when using App Wrapper, I still had an issue with 'base_library.zip'
and code signing, but it appears that it should be located in the
/Contents/Resources folder instead of /Contents/MacOS. I found this issue
discussed at: https://github.com/pyinstaller/pyinstaller/issues/3550
[Solution]
If you move base_library.zip to Contents/Resources
Then provide a soft link:
cd Contents/MacOS
ln -s ./../Resources/base_library.zip base_library.zip

I used to employ a python script which walked through my app and signed
absolutely every file! When it encountered the base_library.zip file, it
would unzip it, sign every file inside, and then zip it again; then sign
the zip file itself and then the app again. Absolute overkill, I'm sure,
but I was a desperate man! Now, with the zip file located with the
resources as described above, just normal code signing seems to work just
fine.

Best regards,
Tim

On Sat, Jan 2, 2021 at 8:51 PM bwoodsend <[email protected]> wrote:

> Hi Tim,
>
> Did you ever managed to get your build signed? We're wanting to add a
> codesign feature to PyInstaller so that you don't have to dismantle your
> build, sign it then glue it back together. Or at least work out what to
> tell users when they ask us how to get it to work. But very few of us have
> access to macOS and none of us know what codesign magic needs to be done.
> Could you chip in your story?
>
> Brénainn
>
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