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I have an Apple M1 Mac mini (model Z12N00038CZ/A) with Ventura 13.5 (22G74) installed. It is my personal (private) computer, i.e. not issued to me by a company.

A few days ago, the iCloud Desktop & Documents Folders option turned itself off and messed up the iCloud folders in the Finder. Then, multiple Documents folder shortcuts have appeared in the Finder sidebar as can be seen in the first screenshot below.

When I try to enable iCloud Desktop & Documents Folders now, the slider always returns to the off position as shown in the second screenshot below.

I have tried logging out and in normally as well as restarting and logging in under the safe mode.

enter image description here enter image description here

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  • Have you tried to log out and then back in with your Apple ID?
    – agarza
    Commented Aug 11, 2023 at 16:49
  • @agarza I tried that now and it didn't help
    – obrsaki
    Commented Aug 11, 2023 at 17:57
  • @Alper When I click on one of the folders, it says The operation can’t be completed because the original item for “Documents” can’t be found. I tried to remove Documents folder and it remove. I tried adding it again in finder setting -> sidebar and when I check that I want to display documents, more and more folders of documents appear in the finder. I already have about 20 of them.
    – obrsaki
    Commented Aug 11, 2023 at 18:04
  • @Alper Thx :). I can't do anything with the documents folder on the sidebar because of the error I wrote. it is strange that 2 folders "documents" and "documents 2" have been created on iCloud. the "documents" folder is empty and when I delete it, it always comes back. The "documents 2" folder is the one that contains the content that was originally in the "documents" folder on the sidebar before this problem.
    – obrsaki
    Commented Aug 11, 2023 at 19:47
  • 1
    I'll let you know how it goes. Thanks for your time and help. You are the best!
    – obrsaki
    Commented Aug 11, 2023 at 22:29

3 Answers 3

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I figured out the issue, at least for me.

Go to Finder > iCloud.

For me, there was a pre-existing Documents and a preexisting Desktop folder. When you turn on the setting in Settings, it wants to re-create these to match the local version. But it detects that they already exist, and that they are not linked to your local folders, and so it then exits the process.

Rename these to something else (I did Documents,, for example).

Then turn the setting on. Then it should work.

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My slider was also also returning to the left/off position. I had moved the "Documents" and "Desktop" folders to my Dropbox folder and created aliases for these folders in my User folder.

After deleting the aliases and returning the "Documents" and "Desktop" folders to the User folder, the slider stopped returning to the left/off position and remained in the right/on position.

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It is hard to say exactly what might have caused these problems on your Mac.

The screenshots and other information you have provided tells me that iCloud and iCloud Drive are turned on and your Mac is not issued to you by a company. The latter is important because companies may prevent the users on their Macs from turning on iCloud Drive or other iCloud features through special software.

I suggest you try the following in the given order (all links are to the related Apple support webpages):

  1. If you have not restarted your computer recently, restart it, login to your user and see if the problems continue.

  2. Restart your computer under the safe mode, login to your user again and see if the problems recur. If they don't, login to your user under the standard mode, i.e. normally, and see if the problems recur.

    If the problems don't recur under the safe mode but continue under the standard mode, it is possible that some software you have installed on your computer that do not come with macOS by default is somehow causing the problems. In this case, login to your user normally, disable any software that starts automatically when you login, logout and login and see if the problems recur.

    If the problems don't recur when all startup programs are disabled, try turning them on one by one and see if the problems resume. Once you identify the program causing the problems, check that program's settings or seek an alternative to that program.

  3. If none of the above works and assuming the computer is not a brand new computer with no files, pictures, videos of yours on it, it would be advisable to have a backup of all your files, pictures, videos, etc. This would not be crucial if your iCloud Drive seemed to work correctly, but it is hard to be sure in your case, so backup your files.

  4. Create a new user with admin capabilities, login to it and see if the problems recur after turning on iCloud with the same Apple ID and iCloud Drive. If they don't, this means somehow certain settings for the original user are corrupted and it is best to continue using the new user. Assuming there is enough space on your computer's drive, stay logged into it for a few hours or more so all your files are downloaded for the new user. If anything appears to be missing with the new user after waiting for long enough, you can either get it from the original user or restore from the backup.

  5. Assuming the problems do not continue under the new user for at least a few days and you make sure that all your files appear under the new user, you can delete the old user to save space.

  6. If the new user does not solve the problems, try reinstalling macOS after making sure that you have a good backup.

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