iCloud iCloud won't sync (Mysterious login item causing issue)

[Loa]

Hello,

I've been having iCloud syncing issues between my Mac Studio and Macbook pro for more than a week now. I created a file on my iCloud drive on my Mac Studio. I see the little pie-chart icon next to iCloud drive, but it's stuck at "0KB of 300MB".

Both Macs have undreds of gigs of free space, I have 20GB of free space on my iCloud plan, internet access is fine and fast on both computers (which are in the same network in the same room).

[Edit: when I start in Safe boot, iCloud works fine. I checked the login items, but there's nothing in "Open at login" and I know all the apps that are allowed in the background and they've been there for months.]
Any ideas?

P.S. The stuck on 0KB thing has been going on for 20 minutes now.

 

[Bigwaff]

You might benefit from installing these free utilities for investigating and diagnosing iCloud Drive problems -

Cirrus & Bailiff

Cirrus – takes control of iCloud, investigates and diagnoses its problems Updated! Cirrus has four main functions. It can download and evict (from local storage) items stored in iCloud so tha…

eclecticlight.co

 

[Loa]

That looks like exactly what I wanted. Thanks!

 

[Loa]

Edit: Safeboot solves my problems, but login items are fine.

Any ideas?

 

[creativesmith]

Wait, did you resolve your issue?
I've encountered iCloud issues of a similar nature. The Mac will not sync with iCloud. And it's been going on for months. Was only recently made aware of it, though—when I noticed that something tiny was endlessly uploading to iCloud. Stuck. Ugh.
Have been in touch with Apple Support for more than a week now, been led through numerous diagnostics, visits to Safe Mode, and a bajillion cold boots. No hint as to the cause. They've gathered a vast amount of diagnostic data and are now working with engineering. Am to hear back from them tomorrow.
The only thing that I could find as a possible issue is a residual listing of a deleted VPN—which, btw, shows that it's disconnected. Am holding off on clicking the "Remove Configuration" button until my response from engineering.

 

[Loa]

I didn't solve the issue, but it solved itself eventually. No idea why. Please share your solution if Apple helps you find one.