In an environment where you use certificates this can happen.

CLientIDManagerStartup.log will mention

Regtask: Failed to refresh MP. Error: 0x80004005

alot of times...

Below I have the 2 fixes!

Fix 1 is to take advantage of the TS Variable SMSTSPostAction to restart the computer once completed
with the value 'shutdown /r /t 0 /f'

This should ensure the cert is requested.

Fix 2:

From testing - after Fix 1 you may need to re-start the SCCM agent.
To do this create a scheduled task that runs on start-up

Program: Powershell

Arguments: -Command "& {start-sleep 120; restart-service ccmexec; Unregister-ScheduledTask -TaskName 'Restart SCCM Initial boot' -Confirm:$false;}"

Run whether or not user is logged on.

Export the scheduled task as 'RestartSCCM.xml' and create a package and command line to run at the end of OSD

SCHTASKS.exe /CREATE /RU system /XML "RestartSCCM.xml" /TN "Restart SCCM Initial boot"

Happy deploying!