Not sure if this will overlap with anyone else, but my experience was a combination of 2 things:
1. Reboots were happening, caused by unattended-upgrade
2. The device causing trouble was a renamed device.
Turns out it was trying to get renamed twice: Once very early in boot from eth1 to eno2, then again based on my neplan from eno2 to the name I wanted. This was failing, and leaving the device down.
Not sure if this will overlap with anyone else, but my experience was a combination of 2 things:
1. Reboots were happening, caused by unattended-upgrade
2. The device causing trouble was a renamed device.
Turns out it was trying to get renamed twice: Once very early in boot from eth1 to eno2, then again based on my neplan from eno2 to the name I wanted. This was failing, and leaving the device down.
See my comment #117 on this issue for more details: https:/ /bugs.launchpad .net/netplan/ +bug/1770082