Sync issue with iCloud Drive

I use iCloud Drive and a Win 11 machine. Files are saved and accessible on PC but shown as 'sync pending' in Explorer. Internet articles suggest to sign out of iCloud to fix the issue.

But: Unchecking the box for iCloud Drive in the iCloud app gives a warning that I may loose files. Which I do not want (duh!).

What to do?

Posted on Oct 3, 2023 10:03 AM

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Posted on Oct 5, 2023 3:37 PM

I just got off the phone with Apple support. The way we fixed it was to sign out of the iCloud, then sign back in. The files were erased off the PC then it redownloaded them once you logged back in.

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10 replies

Oct 5, 2023 10:37 AM in response to Sportster_CH

Hey there Sportster_CH,


Thanks for reaching out to the Apple Support Communities.


Before signing out and back into your Apple ID in the iCloud, do you by chance use any security software on your PC?


If so, let's ensure that the security software isn't  preventing iCloud for Windows from connecting to Apple servers. For steps that can help with troubleshooting this issue, check out this link here: Resolve issues between iCloud for Windows or iTunes and third-party security software - Apple Support


If your security software is causing an issue with iCloud for Windows
* You can't sign in with your Apple ID.
* You see "Verification Failed: An unknown error occurred" or "An error occurred during authentication. Please try again." 
* You see "Your setup couldn't start because your username or password is incorrect" or "Your setup couldn't be started because the iCloud server stopped responding."
* iCloud services won't update. 

Things to check first
Before you change your security software's setup: 
* Make sure that the date, time, and time zone are set correctly on your computer. Learn how to update these settings on a Mac or on a PC
* Log in to an administrative user account, not a guest account. Learn how to do this on a PC
* Update to the latest version of iCloud for Windows or update to the latest version of iTunes.
* Make sure that you have the latest software on your Mac or on your PC.
* Make sure that you set up Windows Hello. Learn how to set it up
* Make sure that you only have one type of security software installed. If you have more than one type of security software installed, you might experience performance issues.


Let us know if that's able to help.


Take care.

Oct 5, 2023 12:59 PM in response to Sportster_CH


Hello Sportster_CH,


Did you restart your computer after turning off your VPN? System wide changes like security require a restart to change.


If that doesn't help, another possible cause is running out of iCloud storage: Manage your iCloud storage - Apple Support


"If you run out of iCloud storage, your device won’t back up to iCloud, new photos and videos won't upload to iCloud Photos, and iCloud Drive and other iCloud apps won't stay up to date across your devices. And you also won't be able to send or receive emails with your iCloud email address."


Thanks.

Oct 5, 2023 12:45 PM in response to Chris_V89

Thanks Chris_V89.

However, this is not the issue. I don't run security software on my PC.

A known possible problem is my VPN. But even completely shutting it down is not solving the problem.

Is there any way to 'force' a sync?


Additional info: all recent files show as 'sync pending', but I can open them fine from my PC.

There are also some old files (some are several years old) with the same status. Those I can NOT open. Strange.

See image (note the time stamps: some of the 'sync pending' are recent, some are old):

Oct 5, 2023 1:25 PM in response to Eric--F

Of course I did...

I can tell you what also is NOT the problem:

  • internet connection - I'm on a wired 1GB connection
  • storage space on my PC or on iCloud Drive - I have ample free space on both (several GB)
  • software updates - all programs, apps, and my operating systems are up-to-date


About the older files: those are available on my other devices, where I can also open them. They don't open on my Windows PC and I get an error 0x800701AA instead.

The recent files (2 months and younger): those are not available on other devices. But they open just fine on my Windows machine where I generated them.

Oct 5, 2023 11:05 PM in response to mcothran2069

Thanks for your efforts mcothran2069.

I'm still afraid that this will lead me to loose files. As explained above, I have two separate issues with the iCloud:

  1. new files that I created and saved on my WIN11 PC do not sync with the iCloud. I don't see these files on my other devices
  2. old files that show on both, PC and other devices' iCloud app, but that I can't open on my PC


I'm not worried about 2. The first is what I'm concerned about. If I log out of iCloud on my PC, then I fear that those new files will be lost.


I developed a workaround, which is extremely cumbersome but is the only solution I could think of. For issue 1., I copy all those new files to a hard drive on my PC (there are 100s, stored in dozens of folders, so not an easy task). Then, for issue 2., I download the files that I can't open on the PC from the iCloud web app and add them to the new physical backup on my hard drive.

It'll cost me probably 8-10h of work. I whish there was a more economical way of doing it. But if there isn't then that's what it takes.

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Sync issue with iCloud Drive

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