I have similar problem.

imac 27" with Ubuntu 18.04 LTS, 4.18.0-25-generic
Thunderbolt display
VGA compatible controller: NVIDIA Corporation GK104M [GeForce GTX 775M Mac 
Edition] (rev a1)

Sometimes, after logging in, both screens are on.
After shutdown, the second screen sometimes is off. 
Then, I have to restart and it could or couldn't work.

Looks like random behavior.

It would be good to have the second screen on since the boot startup.

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which is subscribed to xorg-server in Ubuntu.
https://bugs.launchpad.net/bugs/1771185

Title:
  Secondary monitor not connecting in 18.04 LTS

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https://bugs.launchpad.net/ubuntu/+source/xorg-server/+bug/1771185/+subscriptions

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