@chrisB I am discovering this as well. Here's what I know:

1. This situation occurs anytime I try to upload a modified package for an existing definition in our packages list.


2. Renaming the modified package and uploading it as a new package definition works fine (which generates a new MD5)


3. Only when I attempt to upload a package which has been modified to an existing definition do I get the "upload failed error"


4. This is probably because the modified package has a mismatched checksum and the JCDS errors trying to recreate the checksum

This means any package definition I have in Jamf cannot be updated, but can only be recreated. This obviously breaks links to existing policies and PreStages. I deploy a lot of zero-payload packages that run scripts in a PKG for the exact reason I can only deploy PKGs in PreStages and Patch Management.

Hope it gets some attention, my day just got a looooot longer

@KretZoR: I entered our activation code again, but this didn't help. The only effect I see is that the error message "Upload failed" appears much earlier.

@chrisB Damn..
Jamf Support also suggested to switch primary (principal) distribution point from Cloud to FileShare and then back again, if you've set that up..
Otherwise I suggest you contact Jamf Support! :)

@KretZoR: I switched the distribution point to "None" and then back to "Jamf Cloud" with no effect. I already opened a support ticket yesterday.
At the moment only zipping the PKG files makes uploads possible.

Things are getting even worse: At moment I can't even upload zipped PKG files, and when I want to delete these failed updates I run into timeouts and "Service temporarily unavailable" messages.

Jamf Europe just confirmed that this issue is an EMEIA-wide (Europe, Middle East, India, Asia) problem, and they'll work on it with highest priority.

Thanks for relaying that @chrisB ! For now I will go back to focusing on the other major topic of the day - macOS Big Sur!

@chrisB
Hello,
Thank you for this information.
Do you know if the problem is fixed because we still have the problem. We are still unable to upload files (pkg, zip or dmg) from Jamf Admin to the Cloud distribution point.
All our packages are "Upload failed" in the JSS (no error on Jamf Admin).

Thank you

I can confirm that re-uploading packages to existing definitions in Jamf works. Creating new definitions with names which previously existed in the package list does not work, however. If you rename the package and upload it it should work for now. Long term this is not fixed yet but it's a workaround for the time being.

Today my issue has been solved by restarting the cloud distribution server(s).

@chrisB Have you asked support to do this?

@glpi-ios I opened a support ticket and Jamf finally restarted the server.

What worked for me was creating a new Configuration Profile, then saving it with only its General settings (name, description, etc.) without configuring any payload. Then returning to the saved Profile to configure the payload.

I was having issues with this same error for simple .otf font files until attempting this method which worked for me. If it still doesn't work, consider using your browser in incognito/private mode while configuring the Profile/payload.