Hey guys, just a bit of and update from me on this. I was running into the issue where none of my pre-stages were running. I contacted support and they are aware of this issue. Enabling the above SSL is what we did to get it working, support helped me get that issue sorted.

Hello, I updated following @bentoms link. I just like to leave a followup. The plist that @gshackney posted is pretty much all that I added to our server. I also renewed my token and all was clear. I wish I posted this sooner but have had other projects come up.

Another +1 here for the @gshackney fix being the one that helped us on a Mac server. Restarted Tomcat after editing the plist and DEP synced immediately.

For those following this, the official PI for this appears to be PI-007522

Log into your account and check under My Assets > Product Issues

Still having issues with this, after switching to Amazon Corretto 11.0.5 and forcing TLSv1.2. I ran some packet captures and it appears that Apple is rejecting the initial TLS handshake. Right after our JSS sends the Client Hello, Apple's mdmenrollment.apple.com server sends back a TCP reset packet. TLSv1.2 is being used, the ciphers offered look good, so I opened a case with Apple Enterprise Support.

Had the same issue. Applied the fix detailed in PI-007522, I then had to download a new token from Apple School Manager and upload it to JAMF, but the issue is now resolved.

For those of you who also have SCCM managing your servers. My JSS is hosted on a windows server (which is running the coretto), and I manage it with sccm, after we applied the tls option to java, I still had issues with the web app starting. The solution was to disable or at least stop the SMS Agent Host service and restarting tomcat. It looks they are both trying to use the same port when starting up... port 8005. Once shut down service, the JSS web app started right up. I disabled the service and haven’t tried to restart it yet to see if they can both run but have a set startup order. Hope this helps some.

@alexjdale Did you ever get this resolved?

After resolving this issue, we are seeing some residual affects to macOS devices.

@wkelly1 Yes we were, to a degree. I had to go back to our firewall team since it turned out the connections were being reset by our firewall appliance, but I don't know why this happened at the same time. It was either related or a coincidence, but they were able to whitelist the traffic (again) and it started working. We haven't seen any DEP setup/sync issues since.

Adding TLS 1.2 and a reboot worked for me. Server 2016/Caretto.

@gshackney The fix you posted worked for us. @amityaccounts We also rebooted and refreshed the token.

We are running MacOS 10.14.5, Jamf Pro 10.18.0, MySQL 8.0.16, and Amazon Corretto (OpenJDK) 11.

For folks running the JSS (we are on JSS 10.15.1) on macOS, they will need to update: /Library/LaunchDaemons/com.jamfsoftware.tomcat.plist

You will want to add this to the plist: <string>-Djdk.tls.client.protocols=TLSv1.1,TLSv1.2</string>

<?xml version="1.0" encoding="UTF-8"?>

<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">

<plist version="1.0">

<dict>

    <key>Disabled</key>

    <false/>

    <key>Label</key>

    <string>com.jamfsoftware.tomcat</string>

    <key>OnDemand</key>

    <false/>

    <key>ProgramArguments</key>

    <array>

        <string>/Library/Java/JavaVirtualMachines/amazon-corretto-11.jdk/Contents/Home/bin/java</string>

        <string>-Xms256m</string>

        <string>-Xmx5000m</string>

        <string>-Djava.util.logging.manager=org.apache.juli.ClassLoaderLogManager</string>

        <string>-Djava.util.logging.config.file=/Library/JSS/Tomcat/conf/logging.properties</string>

        <string>-Djava.awt.headless=true</string>

        <string>-Djdk.tls.client.protocols=TLSv1.1,TLSv1.2</string>

        <string>-classpath</string>

        <string>/Library/JSS/Tomcat/bin/bootstrap.jar:/Library/JSS/Tomcat/bin/tomcat-juli.jar</string>

        <string>-Dcatalina.base=/Library/JSS/Tomcat</string>

        <string>-Dcatalina.home=/Library/JSS/Tomcat</string>

        <string>-Djava.io.tmpdir=/Library/JSS/Tomcat/temp</string>

        <string>org.apache.catalina.startup.Bootstrap</string>

        <string>start</string>

    </array>

    <key>ServiceIPC</key>

    <false/>

    <key>UserName</key>

    <string>_appserver</string>

</dict>

</plist>

A huge thanks to everyone for the help I found here, the /Library/LaunchDaemons/com.jamfsoftware.tomcat.plist edit solved the issue for our on premise, macOS JSS.
I wanted to add that applying the latest update (I went from 17.1 to 18) broke the fix as the plist was probably edited and garbled by the installer or server tools.

We high recommend not to include 1 (1.0).

Should look something like this:
Djdk.tls.client.protocols=TLSv1.1,TLSv1.2

Please do not include TLS 1 ( as this is 1.0) and it is deprecated and not secure.

Issue: Kept receiving an "Unable to contact Apple Services" while trying to upload the server token file in Jamf from Apple
Adding -Djdk.tls.client.protocols="TLSv1,TLSv1.1,TLSv1.2" to the Java Options in the Tomcat Properties resolved my issue

Just discovered my on-prem instance of 10.15.1 on Windows Server 2016 was having the same issue. Uploaded public key on Apple Business Manager and downloaded a new token. When I tried to load the new token on JSS I received an error that Apple Services could not be contacted.

Checked services.msc for Tomcat, but that did not have the java tab. Found that you need to launch tomcatw8.exe from <JSS Install Dir>Tomcatin. That allowed me to add -Djdk.tls.client.protocols="TLSv1,TLSv1.1,TLSv1.2" to Java Options. Restarted service, was able to upload token to JSS, and now we're sync'ing.

Many thanks to those on this thread!

@wsapplesupport We had the exact same setup as you except on our Windows Server the .exe to launch was tomcat8w.exe. Thanks to everyone here!

I've been seeing this the last couple of weeks. It doesn't seem to resolved and I am not seeing my new inventory. I've updated my token - what is the solution? - Patti

@gatesp If you edited the tomcat setting with the TLS lines listed above you should be good. But whenever you update your JSS you have to re edit those settings again.

If your still having issues call support and they should be able to step you through it.

Gabe Shackney
Princeton Public Schools

Just ran into this... years later. I had removed these settings at the advice of Jamf support and that immediately broke DEP. Odd that Apple or Jamf haven't fixed this, and it's concerning since Jamf lists disabling this functionality in future versions. =(