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macOS v11.1 Big Sur iCloud drive one way syncing issue, files from elsewhere register but files added (drag/drop via finder) stuck on upload

I'm experiencing one way syncing issues with iCloud drive. I have tried breath of troubleshooting steps, including restarting the device, creating another admin account, signing out (restarting) signing back in to iCloud, removing iCloud then turning it back on, safe mode, and many combinations thereof.


The current behavior is as such. Files edited on iOS / iPadOS sync to iCloud Drive. These files are shown in finder of macOS (v11.1 big sur). Creating a new file or editing the file on mac fails to upload.


If I open iCloud drive in Safari, I can do the following "neat" trick.


Creating a new empty folder on macOS, will appear in iCloud Drive on safari.

Creating a new empty folder on iCloud Drive on safari, will appear on macOS.

Creating a text.txt (utf-8) file in this new folder on macOS will have it get stuck at "uploading" for the 4kb file.

If I upload this file directly to iCloud drive, it will still register as uploading on macOS.


I don't know what else to do to get big sur to upload files.

MacBook Pro 13″, macOS 10.14

Posted on Dec 30, 2020 7:37 AM

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Feb 5, 2021 6:48 PM in response to SumNeuron

I have this exact problem. I have studied it at length and the issue is:


*Files* on my *MacBook Pro* that are *created or updated* do not sync to the cloud. Change any one of the highlighted terms and it works. Folders work anywhere, deletes work anywhere, and creates and changes anywhere except my MacBook Pro work (including appearing on the MacBook Pro).


But here's the fun part. I first experienced this on a 2016 MacBook Pro and got so sick of the problem and Apple failing to do anything about it, and also saying they tried to contact me without actually doing so* that I sold the laptop and got an iPad Pro. Then the M1 MacBook Pro was launched and I couldn't resist. I sold the iPad Pro, got a brand new MacBook Pro and it has *the same problem* as the old one! Better still, the 2018 Mac mini I have works perfectly fine. Did when I had the old laptop and does now.


I have raised it with Apple again and it is currently with engineering. Who have had nothing to say for 3 weeks. And this is exactly how it went last time — 3-4 week wait, followed by my asking for an update and then they'd make me collect more logs, usually in a slightly different way, then 3-4 weeks of waiting... repeat. At the point I gave up it had been 4 months.


After the problem surviving complete wipes of the (2016) laptop and fresh installs of both Catalina and High Sierra, I tried to insist the problem must be in the cloud but was told not to jump to conclusions. Now it has survived a gap of 9 months and a whole separate piece of hardware on different technology and different operating system.


I really think it's in the cloud!


*A senior adviser I spoke to this time told me that there is an "old" way of calling out of the US to other countries where the phone rings on their end but does not connect to the customer, so they think they didn't get an answer, but they're doing the call wrong. Why this is a known problem among some advisers and still happens a year later is beyond me.

macOS v11.1 Big Sur iCloud drive one way syncing issue, files from elsewhere register but files added (drag/drop via finder) stuck on upload

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