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Thank you for researching this. I'm going to (currently) postpone working on this because:
It seems to be fairly complicated - at least there are many steps
There is no guarantee that all of this work will have any impact on the "windows protected your PC" popup. Gum is not super popular so it's possible (likely?) that Microsoft will not accept the certificate and remove that popup.
I'll keep this issue open for now and we can revisit it later.
Seems like there are really 3 things.
I've put everything into a doc for you
How to Sign a file.docx
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