Automated restart problems after Windows10 Update

I have a machine running Windows 10 Enterprise 2016 LTSB and it is supposed to run unattended for long stretches of time (think months or longer). It is running without periphery, so I can only access it remote desktop. As the machine is connected to the internet, it every so often receives Windows updates (which is not a bad thing per se, IMO). Unfortunately, sometimes when it receives an update, the subsequent auto-reboot fails and I have to manually cycle the power to restart it. After such a cold reset, everything seems to be fine and the update is listed as successfully installed. Normal

Question by haarigertroll on Super User, licensed CC BY-SA. We show a short excerpt and link to the original thread as credit.