Hello Tigrenok,
We'll be happy to help. First, let's verify the steps taken to turn on sync Desktop & Documents for iCloud Drive: Add your Desktop and Documents files to iCloud Drive - Apple Support
Next, start up in safe mode and test. This can help and possibly isolate this unexpected behavior:
Start up your Mac in safe mode - Apple Support
"Before you begin
To start up your Mac in safe mode, you need to know what type of Mac you have.
- On your Mac, choose Apple menu
> About This Mac. - Look at the information in the window to determine what type of Mac you have:
- If you see an item labeled Chip, followed by the name of the chip, you have a Mac with Apple silicon.
- If you see an item labeled Processor, followed by the name of an Intel processor, you have an Intel-based Mac.
- Use the corresponding set of instructions below to start up your Mac in safe mode.
Start up your Mac with Apple silicon in safe mode
- On your Mac, choose Apple menu > Shut Down.
- Wait for your Mac to shut down completely. A Mac is completely shut down when the screen is black and any lights (including in the Touch Bar) are off.
- Press and hold the power button on your Mac until “Loading startup options” appears.
- Select a volume.
- Press and hold the Shift key, then click Continue in Safe Mode.
- The computer restarts automatically. When the login window appears, you should see “Safe Boot” in the menu bar.
Start up your Intel-based Mac in safe mode
- Turn on or restart your Mac, then immediately press and hold the Shift key until you see the login window.
- Log in to your Mac.
- You might be asked to log in again.
- On either the first or second login window, you should see “Safe Boot” in the menu bar.
Verify your Mac started up in safe mode
If you’re unsure whether your Mac started up in safe mode, you can use the System Information app to check the mode.
- On your Mac, press and hold the Option key, then choose Apple menu > System Information.
- In the System Information app, select Software in the sidebar.
- In the System Software Overview, look at the value listed next to the item labeled Boot Mode.
- Safe: The Mac is using safe mode.
- Normal: The Mac is not using safe mode."
** It may take longer to finish the start up, and you'll also see some differences in the display. This is expected with safe mode, and when you restart normally, they'll be gone.
After testing, go ahead and restart normally and test again.
Hope this helps
Cheers.
