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Files will not upload to iCloud via iCloud.com

I have been trying to upload several files into my iCloud folder using iCloud.com and each time I get an error message saying "(File Name) couldn't be uploaded. Try uploading the file again later."


I have 1.88 TB (out of 2 TB) of storage space left in my account, so space is not the issue. I have tried uploading in multiple ways...drag-and-drop and using the actual Upload button/tool. Neither works; the error message is the same.


I have never encountered this problem before. Does anyone know why it's happening or how to fix it?




Posted on Nov 3, 2021 3:16 PM

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66 replies

Dec 20, 2021 2:05 PM in response to AllfatherWodan

That might explain why no one has returned my requests for a callback. I did try creating a brand new Apple ID and used it to try and upload a file. That failed too.


I knew it wasn't my Apple ID but was really surprised that a new account still cant upload a dam thing.


...its like Apple just doesnt care here. No way this should be going on this long especially if its a crappy DNS issue.

Jan 7, 2022 9:58 AM in response to rob1234567

Its not the source (browser/windows/iOS etc) - its either the Web API and/or the CNAME DNS issue I found and reported to Apple.


Guys - just find another cloud provider and use them. Just fully encrypt anything before storing it in the cloud, even on Apple's servers if/when they eventually become functional again.


Apple has the decryption keys for your files. If you encrypt them with say Keka for example, they and no one else can ever see the file(s).


Jan 15, 2022 8:51 PM in response to vendorwizard

Yes, vendorwizard, you're correct. I tried to pin it down and found that the filename was not the issue. But somehow manipulating the file was, at least in my case. Something changed, but I don't know what. Unfortunately I don't see any way to edit or delete my previous post.


Just glad I was able to get my stuff uploaded. Maybe this will help someone at least, if not you.

Jan 23, 2022 1:43 PM in response to Hanadark0

Hi. I continue to get the "(File Name) couldn't be uploaded. Try uploading the file again later." I spent an hour or so on the phone with Apple support last week trying multiple browsers and multiple computers and provided the requested error logging information. Apple support called me back a few days later with a request to provide more logging information, but could offer no solution.


Given that this issue is effecting many people for more than 2 months, I declined to spend more time on the phone with Apple or provide additional logging information that was requested. I assume there is nothing special about my computer.


Has anyone actually solved the problem (Apple apparently can't)?

Jan 23, 2022 2:32 PM in response to howard288

I too went thru the same issues with tech support. I gave them tons of stuff, they asked for more. I said NO. I declined to waste anymore time with them. I even showed them the DNS issue and spoon fed Apple the problem. Its still broken.


I wish people would realize it's not their computer nor their choice of browser. Until Apple corrects the CNAME -to- FQDN entry that's borked, this will continue to fail...


Nothing else and I mean nothing else will fix this.


As always I have just recommended to people to just find another cloud storage provider that actually works. There really isnt anything super special about iCloud Drive. There are other options. Google drive works or Dropbox or even OneDrive.


Just remember to fully encrypt ANYTHING you put on a cloud server, regardless of whom the provider is.

Even Apple can view/read/download anything you put into iCloud or iCloud Drive. They hold our decryption keys unless you encrypt it on your own prior to uploading.


I opened a total of 3 tickets and spent hours with Apple engineering and even after showing them via screen share EXACTLY where the problem is, they don't seem to care or have no one left that can fix this simple issue.


Its beyond frustrating. I just dont know anyone internally at Apple to chase this down with..

Files will not upload to iCloud via iCloud.com

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