I have a symbolic link from ~/Documents to ~/Dropbox/MyDocuments.

However I noticed that Catalina from time to time deletes my symbolic link and replaces it with a new Documents folder. I think its happening at a reboot but may happen at other times as well. Any way to prevent this

  • Are you using iCloud Drive? – Allan Jan 20 at 0:28

I have found a workaround for this that I got from the Dropbox forum. As for many years, I 've been syncing my Desktop using Dropbox. However, because of the new layer of security in Catalina, it deletes the folder.

Here is a solution that I did it and it is fine for me now.

After creating the symlink to my Dropbox desktop folder, I locked the link file by displaying its info and checking the 'Locked' checkbox. That seems to do the trick. I checked that I can still write and save to my desktop.

Link: Dropbox Symlinks

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I had a similar issue with the Desktop folder. I would do this :

$ sudo rm -Rf ~/Desktop
$ sudo ln -s ~/Dropbox/Desktop ~/Desktop

And the symlink was replaced by a new folder at the next reboot.

As other users experimented (here and here), it turns out we can not lock a symlink anymore in macOS, the option is greyed out.

I found 2 solutions to this issue :

  • Lock the parent folder (your home folder, /Users/you/) but this will prevent you from adding/deleting files there (source)
  • Disable completely iCloud Drive in System Preferences > Apple ID (Keeping it enabled with "Desktop & Documents Folders" uncheck does not do the trick) enter image description here
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I have another solution to overcome the problem of greyed locked checkbox:

  1. sudo rm -Rf ~/Desktop
  2. sudo ln -s ~/Dropbox/Desktop ~/Downloads/Desktop
  3. Using the Finder, select ~/Downloads/Desktop icon, select Get info from File menu, and click the Locked checkbox (it is not greyed out!).
  4. Using the Finder, copy ~/Downloads/Desktop icon to ~/ (home) folder.
  5. Delete ~/Downloads/Desktop symlink.

You can use another folder instead of ~/Downloads. And you can do the same to have a Documents symlink pointing to ~/Dropbox/Documents.

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