Hi @tcarlson I've had issues with Jamf's built-in reboot payload for a while now. You may have heard this elsewhere, but you are better off setting up an "after" script that performs an immediate reboot:

shutdown -r now

To inform the user a reboot is about to happen, you can precede the above command (or use a "before" script) with something like:

jamf displayMessage -message "Your Mac will reboot immediately following this policy.  Please click OK to continue."

If you do want to debug the built-in restart payload, try adding a custom trigger to your policy and on a test computer, run the policy via terminal (sudo jamf policy -event YourTriggerName) and simultaneously open another Terminal window and "tail -f /var/log/jamf.log".

Hope this helps!