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@kovidgoyal (FYI)
I had a similar issues with a Macbook and an iMac MacOS 10.15.7 + Calibre 5.* I reverted to
Calibre 4.23 and it fix the problem.
The problem: Calibre not opening after update but opening later after 2 - 3 attempts. Once opened it reopened okay but failed to open when I clicked on an epub or awz file. It would start to open and then stop (close)
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