During our enrollment workflow we install a number of required applications, settings, branding, etc and then as the last step force a reboot. Post-reboot, icons now match standards, branding is set, etc and the system is ready for the user to take over. I started noticing that reboots weren’t actually occurring and am now actively trying to troubleshoot it.  My policy originally just used the Restart Option tab, standard restart, and then restarted immediately for both logged in/no logged in user.  At the suggestion  of the Jamf Support AI I moved to an MDM Restart.  Still nothing.  Lastly, I tried removing those and just adding an execution of “/sbin/shutdown -r now” to brute force it.  Still never reboots. Jamf Logs are vague, at best. 

Mon Oct 20 11:33:50 MacBook Pro jamf[1988]: Executing Policy 999 - Enrollment Complete-Reboot (update icon path in script)
Mon Oct 20 11:33:54 Test MacBook Pro jamf[7404]: Checking for policies triggered by "dock" for user "Ed_C"...
Mon Oct 20 11:33:59 Test MacBook Pro jamf[7404]: Executing Policy Dock Settings - Remove Default Icons
Mon Oct 20 11:34:08 Test MacBook Pro jamf[7404]: Adding launchd task com.jamfsoftware.task.checkForTasks...
Mon Oct 20 11:34:09 Test MacBook Pro jamf[7703]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:35:10 Test MacBook Pro jamf[8332]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:36:10 Test MacBook Pro jamf[8375]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:37:11 Test MacBook Pro jamf[8404]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:38:12 Test MacBook Pro jamf[8433]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:40:39 Test MacBook Pro jamf[8550]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:43:07 Test MacBook Pro jamf[8628]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:46:21 Test MacBook Pro jamf[8844]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:49:40 Test MacBook Pro jamf[8942]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:50:56 Test MacBook Pro jamf[8867]: Checking for policies triggered by "recurring check-in" for user "Ed_C"...
Mon Oct 20 11:52:10 Test MacBook Pro jamf[9079]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:55:32 Test MacBook Pro jamf[9181]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 11:59:04 Test MacBook Pro jamf[9353]: The management framework will be enforced as soon as all policies are done executing.
Mon Oct 20 12:14:31 Test MacBook Pro jamf[7707]: Removing existing launchd task /Library/LaunchDaemons/com.jamfsoftware.task.bgrecon.plist...
Mon Oct 20 12:14:56 No Name jamf[1988]: Blessing macOS System on /...
Mon Oct 20 12:49:24 MacBook Pro jamf[1988]: Removing existing launchd task /Library/LaunchDaemons/com.jamfsoftware.task.checkForTasks.plist...
Mon Oct 20 12:49:24 MacBook Pro jamf[1988]: Adding launchd task com.jamfsoftware.task.checkForTasks...
Mon Oct 20 13:20:33 Test MacBook Pro jamf[9593]: The management framework will be enforced as soon as all policies are done executing.

The logs show that it gets blessed for reboot, which makes me think it should be trying to perform the action.  But just never does.  I even get the alert pop on my screen that a reboot will happen. This worked previously fairly well, but now doesn’t.  Has anyone else noticed policies with a reboot action failing? Or any suggested workarounds?