iCloud Upload Error - "try uploading the file again later" - no explanation

Thanks for the idea! As you know, it's not efficient or what we should have to do, but at least I can get my pictures copied to iCloud. It's also a pain to actual download anything as well, so I really hope that Apple will take this seriously and fix this major issue.

Exactly, it's major inconvenience. I have a few different home and work computers I simply can't or don't want to install official iCloud windows software to and sync like billion of photos and documents just to be able to upload a few files a week. If it's not fixed I'll have to move to another cloud service for my documents...

Getting this error trying to upload mp3s to iCloud, How is an issue that affects this many users still in production?

Will probably have to cancel if this doesn't get fixed soon.

Has anyone found a workaround?

@Sparks0829 -

Your response does not address the question. The issue is that the WEB interface for uploading files to iCloud drive appears to have stopped functioning about a month ago. Please acknowledge that you are aware of this issue and advise if Apple is intending to fix it.

I use this feature quite frequently. I am unable to install iCloud for Windows on one of my machines because it is a company-owned machine, but I have frequent need to upload files to my iCloud drive, so I have always used the web interface for this (Chrome browser).

Thank you

This was happening to me as well. The fix is easy:-). All you have to do is click any folder on your desktop. When the folder opens you will see a menu in its left margin. Select the iCloud icon and it will show all of your iCloud folders. Just drag and drop what you'd like into the "small" folders in the left margin menu. Works like a charm.

I'm sorry but your explanation isn't very clear. Do you need iCloud installed on your computer?? Because this sounds like the fix if you have iCloud already installed on your Windows computer. The issue everyone on this thread is having is uploading files to iCloud via web browser (Chrome, Edge), not via the iCloud program installed on your PC.

I don't think anyone here wants to install the iCloud app to their computer as the original way of uploading files via web browser was working just fine up until 3 months ago.

I use a Mac, so this is mostly a Mac fix. Maybe it will work with Windows.

First I have to be sure I’m connected to my cloud account. Then all I do is double click any folder on my desktop. Then a column of small icons appears in a new window. Then you just click on the iCloud icon and a list of all your iCloud folders appear. Then you simply drag the documents from your desktop into the desired cloud folders l. 

I hope this works for you, even though you’re using windows. 

Thanks for trying but that is only a Mac thing. I had Macs years ago and that is obviously the way a Mac works.

There is no way that I know of the get Windows to automatically see the iCloud Drive through a browser.

You have to drag the file into the browser window or select the Upload to iCloud button in the browser window.

And as jakoob said, that just stopped working for us.

THIS IS NOT A FIX, just a TRICK

Along with the files (for which you are getting the specified error) select an extra file which you are able to upload without any error.

So, one valid file with remaining files which you want would let you upload everything what you need.

Then you can delete the unwanted extra file.

This worked for me as a temporary trick.

I have also had this problem for weeks now. But I have been able to get around it by using a VPN.

Which is only convenient for me because I already pay for one, and I have no idea why it works, maybe be its being blocked at the ISP level maybe by a setting in the os. I'm using kubuntu linux and firefox by the way.

I just tossed the towel in on this as well. If you put DEBUG on via Safari, its pretty easy to see a FQDN that points to a CNAME that then points to another CNAME, that doesnt resolve to anything. Obviously thats an issue. Is it the only one? - Well if Safari is looking for this, it certainly will fail.

I've opened up 3 tickets on this over the last 2 months. The 1st two tickets were ignored. The last ticket, I showed them what we found, via screenshots and screen sharing. Problem is, it never seems to get up to the engineers and of course we are never allowed to speak to them directly. Heaven forbid.

I've been told Apple is no longer taking any NEW tickets on this as they are fully aware of it. Well they keep coming back and asking me for MORE debug and MORE information. I showed them and told them virtually everyone out here is having the same issue and it appears to have started around the time Monterey was released. Coincidence? I'm not sure.

But today I gave up. I cant deal with the lack of caring, lack of SKILL within tech support (did everyone join the mass quit-your-job) and overall decline of Apple. Since iOS 14 came out there has been 1 major bug that still isnt squashed. I've opened up tickets and got nowhere. I eventually gave up and went to the dark side and joined Android. Ironically I've yet to have any issues at all. It just works. Imagine that?

I still have a MacBook but once the Samsung Flex 360 5G is released this is being traded in.

Apple is no longer the solid decent company they once were. As a prior poster mentioned, we typically see more effort from startups than Apple nowadays.

I told the tech this morning to close my ticket down. I am done working with Apple as they all seem to be just buying time from us that are trying hard to prove where the issue lies and get it addressed.

For the record, even a brand new AppleID created this am, cant even upload to iCloud.

Good luck guys...it's been a trip

Wow. Lots of people complaining about this issue, and no one appears to have a fix. This doesn't bode well. Do I need to create a new Apple ID? How many? One every couple weeks when their software breaks? Did I really leave Android for this?

I'm so tired of crappy software, horrible interfaces, and companies that just don't care. I don't even have the energy anymore to get upset about it.

I feel bad for people getting new Apple products for xmas and needing to create an AppleID. Won't be able to use iCloud Drive but at least the pix and stuff do still upload and populate iCloud.

Just no files.

Manually upload or drag/drop within macOS will fail.

I tried my best with Apple and even showed them one (more?) of the issues present and they refused to listen and/or correct the problem.

As much as I detest Google products and Android, the stuff just works. It works as its supposed to and issues are quickly addressed if they come up.

Kind of like how Apple was once upon a time, if anyone remembers that way back when..like when we had just ONE iOS release a year. None of this crap sub updates to fix issues that just seem to cause even more issues.

I know Apple has our decryption keys to iCloud Drive and can view/open files if they want to or are instructed by LE.

So common sense is just fully encrypt anything you stash on ANY cloud provider.

I really thought I'd get this fixed after 2 months of fighting but maybe someone else can run this up the proverbial flagpole..

I’m afraid my solution was to install the iCloud app and do uploads from that. Fortunately, my issue was uploading music, and that’s much easier using iTunes. They are actually available more through the music app on the phone, and I couldn’t make that work, even when the web page was working. However, iTunes on Windows 10 is embarrassing. When it crashes (not if) you will likely have to reboot and run it as administrator. As a software engineer, i used to think getting a job with some would be difficult, little did i note that any warm body off the sidewalk would have all the skills they require. Makes me want to send my resume, lol. Wonder if they’d let me work from home in Pittsburgh.

I can confirm this is a problem on macOS Catalina with Safari, hard-wired to the internet. It doesn't matter, WiFi / no WiFi. Apple's iCloud has been broken for some time now. Uploading files from any device, be it a computer or iPhone / iPad, you will see the above mentioned error. It's not an ISP problem --- it's on Apple's own network. I switched to Google Drive, since Apple Support doesn't acknowledge this to be a problem. I suggest you do the same.