iCloud Drive upload error "Try uploading the file again later"

Welcome to Apple Support Communities goodbyegodzilla,

Thank you for posting. Sounds like you are running into an issue when trying to add files to iCloud Drive, is that right? Are you using a Mac or Windows PC? Are there any software updates available for the OS? If using a Windows PC, are there any updates needed for iCloud for Windows?

You can also try using a different Wi-Fi network to see if this continues.

Download iCloud for Windows

I called Apple Support today (11-29-21) on this very problem. I noticed this yesterday and thought things would work their way out overnight. No such luck, I still couldn't copy files from my iMac to my iCloud Drive without triggering the "Try uploading the file again later." message. Apple support did not have an answer and said they would escalate it. I find it hard to believe they don't know about this as there have been a lot of reports for the whole month of November. It appears that iPhones and iPads are not afflicted with this. I moved the files from my iMac to a flash drive, plugged it into my iPad and was able to quickly move the files to my iCloud Drive. I was lucky I had a flash drive with both USB A and USB C plugs on it.

I'm having the same issue. I'm on my PC and trying to upload documents to iCloud. I've done this countless times before without issue. I've never had to download anything in order to do this. Is this a new requirement?

This "issue" has still not been fixed, Apple. It's ridiculous. Users are either tethered to iCloud for Windows if they are non-Mac users, or they cannot drag and drop or manually upload files to the cloud at all. This is PATHETIC. For the time being, you should REFUND users the $2 (or more, depending on the storage being purchased) per month for iCloud until this is fixed.

I concur and have the same issue - when logging into Icloud via Windows I am unable to upload any file to my icloud "Files". When access this via my Windows PC, using microsoft edge, i can login to Icloud, download FROM icloud to my PC, create new foldrers in the icloud 'Files' section which are then visible on my apple devices, but no matter what I do, i cannot upload a file from my PC to the icloud files via a web browser.

Ridiculous.

I'm having this issue too. Can't upload from 14" MacBook Pro or M1 MacMini. Works on my iPad but not from desktops using different networks. I've been working, unsuccessfully with Apple Support for 4 days now.

I am still getting this error (Jan 6 2022). Is anyone else still having issues.

Jan 9 2022 and I’m having this exact issue now too. On top of files not syncing, I also can’t open files already existing in my iCloud Drive.

What a crap answer. Who has more that one Wi-Fi network at home?

It is still doing this. funny thing is Google drive works great.

OneDrive on my Mac works perfectly, just uploaded 40 audio files very quickly, iCloud not so much, actually not at all. Apple has consistently had online issues and it looks like this continues.