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I ran into the exact same problem like some other people here. After clean-installing Monterey to my two machines yesterday (MacPro 6.1 and a MacBook Pro 15" Late 2015) my iCloud Drive got stuck syncing on both machines!

If I try to copy folders within the folders in iCloud Drive (documents / desktop / etc.)I get this Error: Finder cannot complete the operation because some data in “” cannot be read or written Error -36

If I click on a folder's cloud icon to download it it says folder "" can't be downloaded check your internet connection. But I am online, no ports are blocked.

Copying files is not a problem! Just folders. When I deactivate iCloud Drive I can copy folders on my desktop without any problems.

The same problem is also documented here: https://discussions.apple.com/thread/253885938?page=2

What I did:

Nothing worked. Just deleting the CloudDocs Folder helps for a couple of Minutes. While it starts resyncing I can copy folders an everything is ok till it finished syncing. Then the problem is back.

So what I can do?

Would be great to get your help and expertise!

12557
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  • not sure about the iCloud sync issue but I do know that the -36 is a premature end of file error in the file system. In other words the file is damaged, somehow. You may want to run Disk Utility First Aid and let it scan your data volume for problems. – Steve Chambers Feb 15 '23 at 20:26
  • Don‘t think so. Both machines are freshly formated and clean installed with Monterey. Both with the same problem. I found some topics with the same problem, the -36 error is always part of that problem. If i generate a new file or folder its the same. The problem is that icloud drive gets stuck again and again… – 12557 Feb 15 '23 at 22:43
  • You’ve got two very different machines which are what I assume running the latest version of macOS. I would check two thing: downgrade one of the machines to Catalina and see if that helps. Next, use https://speedtest.net and ideally iPerf3 Public servers to check your internet speed. If you have high latency things may be timing out. – Allan Feb 15 '23 at 22:48
  • Ok i will check the speed which was never a problem when i was on Catalina. Both machines are supported for mac os 12. – 12557 Feb 15 '23 at 22:58
  • Speed Test was: down 46 up 25 ping 10 – 12557 Feb 16 '23 at 08:11
  • the -36 is a file/filesystem error, has been back to Classic Mac OS. Freshly formatted and new O/S has no bearing on user files as the macOS installer doesn't touch user files. You may have run into a bug in macOS, iCloud or a number of other things, or the source file may be damaged. The thing with troubleshooting is to try everything, even if you don't think it could be the problem. because sometimes that long shot, "couldn't be that" actually was the cause after all. I've seen it over and over again. The only problem with AD is we can't get our hands on your Mac, we can only advise. – Steve Chambers Feb 16 '23 at 21:15
  • Thanks Steve. You are right! Strangely enough, the error disappeared on my Macbook after I did all the steps in the one post and ended up completely disabling and re-enabling i Cloud. On my Mac Pro I do not manage to do this. – 12557 Feb 17 '23 at 07:48

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