I had a similar problem with my Dell Latitude 5289 using Ubuntu 17.10.
After trying different things, I got it to work by using hdajackretask.
I got a clue from norteo on this thread:

https://askubuntu.com/questions/926590/headphone-not-working-on-
ubuntu-17-04-dell-xps-15

To get it to work for my specific setup, I ran hdajackretask, checked
the box to "show unconnected pins," selected "override" for pin 0x21,
and set it to "Headphone." I did not override or adjust any of the other
pins.

I realize you're using a different version of Ubuntu, but I hope this
might help you or someone else using a Dell Latitude 5289.

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https://bugs.launchpad.net/bugs/1728093

Title:
  [16.04, ALC3253] Dell Latitude 5289 Combo Jack Does Not Recognize
  Devices

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