I got the macOS Sierra update when it went into public beta, and I've been trying to use the automatic Desktop / Documents upload feature with iCloud Drive.

I've enabled the feature, however since September 7 no files have been uploaded. By this point, the bottom of my Finder windows say:

15.78 GB available on iCloud, uploading 156,106 items (543.2 MB of 543.2 MB)

However the files are never actually uploaded. I keep my screenshots folder on my desktop and I take a lot of screenshots, so I can see that September 7 was the last date any file was actually uploaded.

What should I do? Is there a way I can disable and re-enable the feature without risking loss of data? Are there any solutions to this problem? What should I try? So far I've tried rebooting, and tried software update to macOS 10.12.2 public beta.


Happened to me as well, here is what I did:

  1. Back up all items in the Documents and Desktop folders
  2. Open up System Preferences
  3. Click on iCloud
  4. Click on Options next to iCloud Drive
  5. If Desktop and Document Folders is disabled, enable it
  6. If it enabled, un-enable it.
  7. Uncheck the Optimize Mac Storage and click Done
  8. Redo the opposite of this to re-enable iCloud
  9. Move all Documents and Desktop items back to their respective area.

It is helpful to note if you are experiencing sync issues in any of the other categories in iCloud Drive, try disabling them and then re-enabling them.

  • Since not all items are backed up won't this cause a loss in data? It displays a warning about how documents will be removed... – Luke Taylor Dec 15 '16 at 5:56
  • @LukeTaylor I don't think it should wipe anything from your local storage, and when you turn it back on, it will start the sync again, replacing all duplicated files. – Rushil Srivastava Dec 15 '16 at 22:45
  • 1
    Unchecking the box brings up a warning that "if you continue, items will be removed from the Desktop and Documents folder on this mac and will remain available in iCloud Drive". It's kind of ambiguous about how it will treat unsynced items. – Luke Taylor Dec 15 '16 at 22:49
  • @LukeTaylor, In finder, do you see the iCloudDrive on the top left? Click on it and let me know if your files are inside the documents and desktop folder – Rushil Srivastava Dec 16 '16 at 1:05
  • They are, but I haven't yet disabled the iCloud sync for these. Most of them have the ☁️ icon indicating that they haven't yet been uploaded. – Luke Taylor Dec 16 '16 at 1:19

Have you changed the date and time on your computer or phone? This is a possible explanation of why iCloud is not syncing.

  • They're all correct. I rely on those times and dates daily, I'd know if they were off. – Luke Taylor Feb 13 '17 at 2:40

Be careful, this method will Delete the files. Managed to solve it by:

  1. Go to System Preferences
  2. Select iCloud
  3. Untick iCloud
  4. At the prompt select Remove from Mac
  5. At the next prompt select Stop Updating and turn off

Should be fixed, worked for me, really annoying

Second scenario that worked, on iPhone:

  1. Open Settings
  2. iCloud Drive
  3. Manage Storage
  4. Click on the folder that's at fault and remove it from iCloud

You can try the following command from the console. It will recursively traverse your directory while updating the last modified date of each file. It will do this for all files but "*.icloud". The command will also print the name of each updated file.

go to the iCloud directory,

cd /Users/admin/Library/Mobile\ Documents/com~apple~CloudDocs

Please: double check that you are in the directory above. Use pwd

and trigger the date update for those files

find . ! -path "*.icloud" \( -exec echo {} \; -a -exec touch {} \; \)
  • Can you please explain what exactly this command does? – pkamb Dec 25 '19 at 23:03
  • yep, the answer is updated. – user9869932 Dec 27 '19 at 13:10

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