Sonoma 14.4 syncing problem between devices

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.

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.

Having a look right now.

Will dissect it in detail and get back to you shortly

Very much agree on the Private Internet Access Application

Good one there 😎

To each their own

So unhelpful to just cut and paste boilerplate articles that shift the blame the customer instead of admitting how buggy this OS update is, and fixing it.