This is a recent issue and I'm beating my head against a wall trying to figure out where it's stemming from. After a machine is imaged, almost 100% of the time, it won't run policy the first time it boots up. My Check-In > Startup Script page has every option checked off on it (most importantly ensure ssh is enabled and check policies for startup). But our login options aren't set, SSH isn't enabled...none of the policies ran that were supposed to after startup.
Up until recently, another reboot after it hit the login screen would succeed in kicking the agent into gear and getting the start-up script to run. Now, no matter how many reboots we give a system, the jamf agent will not start checking in until someone manually runs jamf policy from the terminal.
Any assistance on this would be greatly appreciated. Thank you!