MacOS – iCloud Drive is stuck uploading items and no longer syncs

data transferfindericloudmacos

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.

Best Answer

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.

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