Weird Safari Bookmark Issue

I have a strange issue with Safari on macOS 10.15.3 that I cannot seem to get past. Periodically, when I launch Safari, I get a message such as this:

I don’t know why Safari is pointing to the 1Password keychain. Anyway, if I click “Cancel” then Safari hangs and never recovers. (I’m on Chrome now as I write this.)

The other day I turned off Safari sync in iCloud on the Mac and my IOS devices. Deleted Bookmarks.plist from the Mac. Downloaded a copy of Bookmarks.plist from Backblaze from a date well before this issue started. I added that to ~\Library\Safari. Then I turned on Safari in iCloud on the Mac. Waited. Turned on Safari in iCloud on each iOS devices – waited in between devices.

All was well for a couple days. Now the problem is back. I don’t know where it is originating or what else to do to troubleshoot root cause.

Yeah, I actually wrote an article about this awhile ago but I don’t think I ever published it anywhere.

The gist of it is this: the Bookmarks.plist file is now protected by macOS with some high-level super secret sauce that always seems to restore your old bookmarks, whether you want them or not. I tried all the things you described and had the same experience.

Here was the workaround that worked for me:

  1. Quit Safari

  2. Turn off your Internet connection (turn off AirPort is the easiest way, unplug from Ethernet if you have it).

  3. Restore your old Bookmarks.plist

  4. Launch Safari

  5. In Safari, go to File » Export Bookmarks… which will save them as a special HTML file

  6. Turn your Internet connection back on.

  7. Add some new, meaningless bookmark to Safari and call it something obvious like “THIS IS NEW”

  8. Wait for that new bookmark to show up in Safari on all of your devices

  9. Delete all of your Safari bookmarks

  10. Save some new, meaningless bookmark to Safari like “THIS SHOULD BE THE ONLY ONE”

  11. Wait for all of your devices to show just one bookmark (the one from step 10)

  12. In Safari on the Mac, use File » Import From » Bookmarks HTML File… and import from step #5

  13. (Optional) Set yourself a calendar/OmniFocus/Things/Reminder repeating event to export your Safari bookmarks to an HTML file every month or so

I don’t know why, but importing from that HTML file worked when nothing else would.


Thank you! Very thorough.

I’ve taken a slightly different tack. I clued into a pattern when I noticed that the files that Safari was prompting me to locate for it (and then freezing) were all file:///... URLs.

How these crept into my bookmarks, I’m not sure, I have well over 15 years history in my bookmarks – but those files definitely do not exist on this machine. Safari chokes on Catalina chokes on them. Perhaps it’s a security issue. I don’t know.

  1. In System Preferences > iCloud I turned off Safari to stop the bookmark syncing.
  2. I opened Chrome and had Chrome import bookmarks from Safari – at this point the import contains “missing” “file:///” bookmarks from Safari’s perspective (that’s my interpretation.)
  3. Bookmark management is easier in Chrome, so I could search for file:///... URLs there and delete those bookmarks. Here I recognized the names of the bookmarks Safari chocked on.
  4. I deleted the Bookmarks.plist file from ~/Library/Safari
  5. I opened Safari (still with iCloud Safari sync turned off) then imported the Chrome bookmarks.

I’ve turned on Safari sync in iCloud settings on the Mac again. Still crossing fingers this worked. If not I’ll try your recipe @tjluoma.

Thanks again!