Tesh2886 Said:
"Preview file damaged post annotation: […]my question (and frustration with Preview) is more regarding the lost annotations and not as much the lost file. Why do annotations keep getting lost - either by somehow wiping off the file, or, in the latest instances, by just losing the file itself?”
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Troubleshoot the Install:
No. This should not be occurring. I think you may have a bug in the Operating System. So, try troubleshooting a few things, and if none of them work, then it is time to fix the operating system.
A. Single Out this User:
For temporary use, create a new administrator, seeing if you still get this error. If you do get this error, then it is an error in the macOS. If not, then it is an error with just the current user.
B. Boot into Safe Mode:
Hold Down the Shift Key upon boot. Once at the login screen, release shift. See if it all now works. Get In Safe Mode, only necessary items load (i.e. the caches), and new preferences are set aside. So, try this in Safe Mode seeing if this no longer occurs.
C. Restore from a Backup:
Do you have a Time Machine Backup of your Mac that you created prior to this? If so, restore form it. If not, take this as a learning experience, knowing to always create a Time Machine backup of your Mac prior to making any major change to is (i.e. macOS upgrade), so that you can have something to restore your Mac from, should anything go wrong with the reinstall.
If nothing above works, then...
D. Reinstall the macOS:
Nothing would be lost, it's just that sometimes changes are made to your system, and then then processes become corrupted, technically. When reinstalling, deleted files are reinstalled, and misplaced files are moved back to where they should be. Go Here: How to Reinstall macOS from macOS Recovery - How to Reinstall macOS from macOS Recovery - Apple Support