I have to Reset Pihole Password After Container Restart

[Bucking_Horn]

@BlueWings

This was the same config I used for few months and I did not have password issues until latest update.

That would be the expected behaviour if that container has been running without interruption during all that time. As an update requires a restart, that would be when a new random password from %randomAdminPassword% would have been set.

@BlueWings

So when do you have to use sudo pihole -a -p ? Only in non docker installations ?

Yes.
As mentioned before, use the WEBPASSWORD environment variable for a dockered Pi-hole.