Us too (10.17 on-prem) . All three of our Jamf environments stopped synching with Apple on 9/12 at about 17:00. I tried to upload a new token to our development instance (to see if it fixed it) but now get the "Problem Contacting Apple Services" message....

We are experiencing the same issues ALL our DEP-Sync are failing........ but our 6 caching servers are working and syncing fine.
Renewed all tokens... restarted our Jamf Pro and DBServer ... nothing changed all are sync failures

Looks like Apple reinstaed their change that broke TLS 1.3

You need to do the fixes listed in this Post:

https://www.jamf.com/jamf-nation/discussions/34219/dep-sync-failing

We need to add the following line to the JAVA_OPTS area of setenv.sh:
-Djdk.tls.client.protocols=TLSv1.1,TLSv1.2
Default filepath on Linux:
/usr/local/jss/tomcat/bin/setenv.sh
This will need to be done on all Tomcat servers. Tomcat will need to be restarted after doing

@jhalvorson the steps from this link worked for me. Needed to allow TLSv1.2, Restart Tomcat, Renew DEP Token, and all was good. The syntax needed is all at the link. Thanks for pointing me in the right direction!

bcourtade´s post solved it for us with JAMF 10.16.1 !
https://macmule.com/2019/10/01/more-dep-sync-errors/

@martenblank I appear to be having some DEP issues even after using that method to fix in v10.17.1

Running into PI-006472: UserList mdm command continues to be issued (and fails) when required preconditions are no longer met)

Some computers are having issues re-enrolling via methods provided by support. My theory is DEP related as I see errors in logs and devices assigned to prestages not showing as such in the Automated Device Enrollment section in JAMF Pro.

If you are still having issues, check with your firewall team as well. We had to have our FW team trace our traffic and re-allow it for mdmenrollment.apple.com. Not sure what could have changed since we had all of Apple opened and it was working before, but it was more than the Java/TLS 1.2 change for us.

After editing and saving my prestages as suggested by JAMF Support, now getting the following error after invoking

sudo profiles renew -type enrollment

Selecting details, and accepting enrollment

I was having the same issue. Apple School Manager was last connected to the MDM on December 9th. Our infrastructure was upgraded to 10.17.1 on the 4th of December.

Process I used to fix the sync was.
1) Add the TLS first in our Ubuntu server.
2) Then Renew the DEP tokens. Even though we were still within the time frame of expiration, it still worked.

Cross reference https://www.jamf.com/jamf-nation/discussions/34219/dep-sync-failing for another solution that fixed the problem for us.

I just performed an on-premise install (my first install), 10.19.0 here. Ran into the same issue when adding the MDM to Apple Bus. Mgr. The TLS adjustment to Tomcat advice from above fixed it. The page linked from above that showed the Handshake-error log entries were immensely helpful.

In my case, I needed to forward port 5223 to my Jamf Pro server.

Semi-old thread resurrection, but, is anyone experiencing issues today with this? I just noticed several ABM assigned Macs that I've added to a Prestage are still awaiting sync and in my ABM setup in Jamf it's saying Sync Failed - Awaiting Next Sync.
I tried re-uploading a token from ABM into Jamf and I'm getting the "Problem contacting Apple Services" error.

See, this is the kind of crap that keeps me up at night. ABM + DEP is cool and all, but it's relying on a process that could go down at any moment and we have zero control or influence over it. If this is on Apple's side, the only thing I can do is sit and wait and hope they address it sooner rather than later. I was just about to ship out several Macs to customers when I noticed they weren't syncing over to the Prestage, which I'm glad I checked. Gonna hold onto these machines until I know things are communicating again. *sigh*

Same issue for me. Been going on for some weeks though.

Awaiting sync is the error I see in the pre-stage and under device enrollment settings.

I AM able to upload a new token without issue.

I have a support ticket open with Jamf but this is yet to be resolved.

@Daikonran
The time setting saved me. 2021 and still useful. Thanks :-)

I run into the "Problem contacting Apple services" error every year and then forget the solution by the next year 😅. Adding the solution for my future self and anyone else with the same issue.

The token must be downloaded from Apple Business using the same account that you've used for previous renewals. If downloaded from a different Apple Business account, you will get this error when uploading the token to Jamf.

Hope this is helpful to someone!

I too got the same error message. Today is the last date for us to renew the Automated Device Enrollment Server Tokens. It assumed that the time may be expired, however expiration date only mentioned on the Console.