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Force a MacBook/iCloud Drive Sync?

Everything except for some small percentage of documents on my MacBook is synced to iCloud. Just two document folders have the little grey cloud by them. In fact, when I click on the little cloud next to "iCloud Drive" I get: "iCloud is not syncing - There are pending items to sync." It has been this way for months. I cannot tell which specific documents are misbehaving and I do not know how to force a synchronization.

MacBook Pro 16″, macOS 13.2

Posted on Feb 11, 2023 1:47 PM

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Question marked as Top-ranking reply

Posted on Mar 3, 2023 1:23 PM

This is ridiculous. My iCloud is not syncing on one MacBook... this is like the third time this has happened over the last year. Telling me that iCloud has pending files to sync is laughably unhelpful. Why not tell WHICH files are pending so I know where to start looking?


Doing a complete re-download of cloud files is unreasonable. I used Dropbox for many years and never once had to do this on any device. Maybe Apple should consider hiring some Dropbox people to help them get the bugs out of iCloud. These problems have been going on for a number of years. Certainly longer than the old Apple would have tolerated.

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Question marked as Top-ranking reply

Mar 3, 2023 1:23 PM in response to justin_900

This is ridiculous. My iCloud is not syncing on one MacBook... this is like the third time this has happened over the last year. Telling me that iCloud has pending files to sync is laughably unhelpful. Why not tell WHICH files are pending so I know where to start looking?


Doing a complete re-download of cloud files is unreasonable. I used Dropbox for many years and never once had to do this on any device. Maybe Apple should consider hiring some Dropbox people to help them get the bugs out of iCloud. These problems have been going on for a number of years. Certainly longer than the old Apple would have tolerated.

Feb 13, 2023 3:11 PM in response to JB's Forum Name

Hello JB's Forum Name,


Welcome to Apple Support Communities!

We want to help ensure the files are syncing to iCloud Drive as expected. Are you using the files with another file management service? See here to ensure your settings are correct:

"On your Mac

  1. Go to Apple menu  > System Settings or Apple menu  > System Preferences, then click Apple ID. 
  2. Select iCloud.
  3. Sign in with your Apple ID, if you need to.
  4. Turn on iCloud Drive.

To add the files from your Mac Desktop and your Documents folder to iCloud Drive, turn on Desktop and Documents

  • You can then find your Desktop and Documents folder in the iCloud section of the Finder sidebar. 
  • If you add a second Mac Desktop, you can find the files in your Desktop and Documents folders in iCloud Drive, in a folder with the same name as your second Mac. The files from your second Mac won't automatically merge with the files on your first Mac.

If you already use a feature from another cloud provider that syncs or manages your Desktop and Documents folders, you need to turn it off to use Desktop and Documents. Desktop and Documents requires macOS Sierra or later."

This Apple Support page has the full details: Set up iCloud Drive - Apple Support


Since it sounds like you've already take these steps, does a normal restart of the Mac have any impact? Does testing while connected to another network help isolate the issue?

We hope this helps to get the files to sync as expected again.

Cheers!


Feb 13, 2023 5:09 PM in response to justin_900

Justin, thank you for your response. Yes, iCloud sync works for most everything and restarts do not help. You do have me wondering if our two MacBooks, two iPads and two iPhones (all with the same Apple ID may have something to do with it. The vast majority of my files were made on the one MacBook possibly some were made on the other. I have iCloud syncing set on both but maybe the second system is the problem.


I can see that the folder is not syncing but I do not know how to determine which particular files are an issue without a simple stare and compare.

Feb 13, 2023 5:19 PM in response to JB's Forum Name

Hi JB's Forum Name,


A good step to isolate potential software or user configuration problems is to test in safe boot. How to use safe mode on your Mac outlines the specific steps to complete to perform this test. Additionally that article provides follow-up steps depending on the results of the test to further isolate or address common problems.


If those don't help, reach out to Apple Support directly for further investigation into this.


Regards.

Feb 14, 2023 8:22 AM in response to Bill_T1

Thank you Bill, safe mode did not help and for kicks I also ran first aid. Then I tried stare and compare on two of the three directories that had the 'iCloud is not syncing' note. A weird thing is even though I have the little cloud that says there is a problem, all the files in iCloud had the same date and time as the files on the MacBook.


I think I will see if Apple Support has any guidance.

Mar 3, 2023 7:56 AM in response to SparkleTaco

Taco,


Turned off and then back on; yeah, it worked! Unexpectedly if created an iCloud Archive directory on the MacBook and the took a looooong time syncing/loading. I still do not quite understand that or where the original files are stored on the MacBook. Luckily the MacBook has tons of space so I am not spending anymore time trying to figure it out! Hope it works out for you!

Force a MacBook/iCloud Drive Sync?

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