Sonoma 14.4 syncing problem between devices

I've managed to resolve my issues but it took quite a while and several attempts. What I did was:

1. Found this page online - https://apple.stackexchange.com/questions/465092/why-does-icloud-brctl-say-that-i-have-136-client-truth-unclean-items-unsynced - and downloaded the icloud_ubiquity_fix.sh from the github repository.
2. Installed a newer version of bash via brew (brew install bash). If you don't have brew installed install it from here (https://brew.sh/)
3. Backed up my Desktop and Documents folder (or confirmed I could access a Time Machine backup of my Desktop and Documents).
4. Turned off Desktop and Documents syncing in the iCloud settings page.
5. Using the web based iCloud Drive (https://www.icloud.com/iclouddrive/) I cleared out all the iCloud Drive Desktop and Documents and emptied the trash/ bin.
6. Rebooted the Mac.

Once logged in I then:

1. Restored my Desktop and Documents from the backup.
2. Created a Desktop-new and Documents-new in my home directory and moved the contents of Desktop to Desktop-new and Documents to Documents-new. This ensures nothing will try to sync when I turned syncing back on.
3. Opened a terminal and ran 'brctl status'. If there are any 'Client Truth Unclean Items' it means there are files stuck in the queue.
4. Ran the icloud_ubiquity_fix.sh to resolve any issues. At this point I had a load of ghost files appear in the iCloud Drive folder which I deleted and emptied the Trash.
5. Ran 'brctl status' again. If there were still issues I then removed all the files from the CloudDocs folder using Terminal: 'rm -r ~/Library/Application\ Support/CloudDocs/*'
6. If the bird process wasn't running (ps aux | grep bird or view in Activity Monitor) I logged out and back in again.
7. Went through steps 4-7 again until it said there were no stuck items found.
8. Rebooted the Mac.

Once logged back in I then:

1. Turned on Desktop and Documents syncing in the iCloud settings page.
2. At this point there are no files in either iCloud or the Mac's local folders so nothing will sync.
3. Opened a command prompt and ran 'brctl monitor -i com.apple.CloudDocs'. This will run continuously and show progress of syncing.
4. Moved a single file from Desktop-New to Desktop and watched the terminal window. If it's working correctly you'll see a load of information start scrolling and eventually stop. If all is well you should have a copy in your iCloud Drive (which you can view online at https://www.icloud.com/iclouddrive/)
5. Now move the rest of the Desktop-New items back into Desktop and let it all sync.
6. If that works then start to move items from your Documents-New back into Documents. I recommend moving a folder at a time and letting the sync complete before moving onto the next. Also compare the web based iCloudDrive to confirm files have been updated.
7. Once everything is completed reboot the mac and log in.
8. Run a Time Machine backup to save the new state of the Mac (so you have a restore point.)

Before calling Apple, if I may suggest 😎

Running 1 M1, 1 M2 and 1 M3 all with Sonoma 14.4

Do not experience any of your previously outlined issues

To avoid the question / answer and question answer scenario

Suggest the User starts with the Top Suggestion and test. 

Thereafter,  move down to the next and test again. 

Keep on going in the Order that they have been presented or until you reach the Final Suggestion 

Restart in Safe Mode. This will perform a Disk Repair, clear cache files and only load Apple Software, extensions and fonts. The boot up will be slow and can take some time - Normal.

Safe Mode will also eliminate Third Party Software, extensions and drivers from loading. It will only load the Minimum amount of Core Apple Processes to allow the the computer to function at a reduced Level of Performance 

Does the issue present in this mode ?

Sometimes a Safe Boot followed by a Normal Boot will just put things right.

If not - there could be something in the main User Account playing up. To further isolate this - Set up users, guests, and groups on Mac. Then log out of the Main User account and log into the dummy account and test again if the issue persists.

If the issue is present in the dummy account - then, this appears to be a System Wide issue on the computer.

Download the Application Etrecheck  ( External Link ) directly from the Developer.

The Application is Not a " Silver Bullet "  and is  only a tool to examine the Hardware / Software used on this computer 

This is a Diagnostic Tool that makes no changes to the computer Hardware / Software used on this computer 

The application is free or paid from added features. 

The Report will Not Reveal Any Personal Information. 

Post back the Full Report - copy and paste - >>>> using the Additional Text Icon ( 3rd Icon to last ) <<<<

Lastly - should you decide to use and post the Report now or at a later time, we are willing to have a very close look and offer some insights 

Here are some solutions to fix iCloud Drive not syncing on your Mac:

Check Internet Connection

Ensure the Mac has a stable internet connection, as iCloud requires an internet connection to sync files.

Update macOS

Updating to the latest macOS version can fix bugs and improve iCloud syncing performance. Open the System Preferences app, go to Software Update, and install any available updates.

Check iCloud Storage

If your iCloud storage is full, it can prevent files from syncing. Check your available iCloud storage and upgrade your plan or remove files if needed.

Paste a new small file to iCloud Drive in Finder

Sometimes this can kickstart the syncing process

Check for recent large or corrupted files

Trying to upload these to iCloud Drive can sometimes interfere with the syncing process. Finder will often freeze. Go to iCloud Drive in Finder and look for any recent files you have created which are trying to upload to iCloud Drive (designated with a cloud symbol without the down arrow). Archive.zip files can cause a particular problem. Try to open or delete the file to restart or stop the uploading sequence. Restart the Mac and see if the problem clears

Restart Bird Process

The "bird" process manages iCloud syncing on Mac. You can try restarting it by opening Activity Monitor (in Utilities), searching for "bird", quitting the process, and then reopening a Finder window.

Reboot in safe mode

Shut down the mac. Press and hold the start button until loading startup options appears (Apple chips).  Select Macintosh HD, press the Shift key on your keyboard and the press Enter on your keyboard. Safe Boot will appear in red in the top right. Key in your password and wait for the system to load (you may have to do this twice). Check if the sync problem clears (give the system say 20 minutes to sort itself out). Restart the Mac (it will restart in normal mode).

Sign Out and Back Into iCloud

Sign out of iCloud on your iMac, restart the computer, and then sign back into iCloud. This can sometimes resolve syncing issues. Can take a while.

Reinstall macOS

Reinstall a fresh copy of macOS (this doesn’t affect existing data or apps). Shut down the mac. Press and hold the start button until loading startup options appears (Apple chips). Select Options, then Continue. Select yourself as the User and type in your password. Select Next, then select Reinstall macOS. Can take a while.

If syncing suddenly stops working properly then it is likely to be a file that has recently been created or transferred to iCloud Drive. Look for the upload symbol next to files in iCloud Drive and identify the most recent ones. Try copying these to a local folder on your Mac and then reopening them. Should indicate if they have a problem. Files I have had a problem with are unusual file types, images, large files and archive.zip files, so not always corrupted ones. Patience and trial and error. Sometimes I get an instinct for the problem file, but nothing scientific to it. I hope this helps.

I am unfamiliar with TripMode filter but might it intervene with iCloud? "Optimize your Mac's data usage by blocking unwanted background updates."

You might also try to uninstall privateinternetaccess.vpn.

A few further thoughts:

Once you've identified the problematic file, move it out of the iCloud Drive folder, then move it back in. This can trigger the sync process to restart and complete the upload.

Create a new file in the problem folder: Another trick is to create a new file in the folder that is having issues uploading. This can sometimes kickstart the sync process.

Check for special characters in the file name: Files with special characters in the name can sometimes get stuck during the upload process. Try renaming the file and moving it back into iCloud Drive.

I have the same issue since installing 14.4. Finder locks up and iCloud Drive syncs either fail to complete or sit at uploading without changing until I either log out or reboot the Mac. Then they run for a while before stopping again. Changes do not appear in the iCloud Drive so currently I only have the files on my Mac.

The 'bird' process also vanishes and cannot be restarted without logging out/ rebooting.

Definitely something up with 14.4.

Add in the Suspicious Package - /Applications/Suspicious Package.

Generally suggest not using any Commercial VPNs at all for a variety of reason

They are not adding any additional Protection for the Bad Actors on the Internet for one

https://gist.github.com/joepie91/5a9909939e6ce7d09e29

Added, are the results from the Diagnostics Information (past 60 days): aspect of the report

Some, of which could be directly relate to Internet Access issues

Below is just 1 of a whole Host of other crashes

2024-03-16 21:53:55 bird - Crash (313 times)

The " Bird " process from my present Activity Monitor >> View All process >> Network >> Inpection >> Open Files

System/Library/PrivateFrameworks/CloudDocsDaemon.framework/Versions/A/Support/bird

iCloud Sync issue you have been reporting as Main Issue Sonoma 14.4 - right ?

I am a normal user, not a representative of Apple or trying to defend Apple. I am running Sonoma 14.4.1 on an M1 iMac and it is working fine at present. The above is a list of things I check when I am having a syncing issue. My most recent problem was a corrupted file trying to upload, which was interfering with the syncing process and causing Finder to hang. Once I removed the file, normal syncing was restored. It wasn't a bug in the system.