Steps to reproduce on Mac Chrome Version 87:
1. Pack extension locally
2. Drag packed extension
3. Extension is disabled with the following error: "This extension is not listed in the Chrome Web Store and may have been added without your knowledge" . See attached screenshot.
4. Increment version and add new permission
5. Pack extension locally with same pem file
6. Drag packed extension
7. Permission dialogue appear - click cancel
8. As the extension is disabled, I'm not able to experience my users' experience of what happens after an update.
I hope this clarifies things.