Citizen Sleeper

Short version: Complete Ethan's tasks before disabling your tracker and/or leaving the station.

Detailed version:

Around Cycle 10, Ethan shows up at your home to collect a bounty on you. What you do here doesn't really matter, he will tell you to pay his bar tab. The Kompressor Club icon appears with nothing to do for 4 cycles.

After 4 cycles, you will see an option to pay Ethan's bar tab. Do so, go through another dialogue (choices don't matter) and he will go back to drinking. (If you don't pay his tab on time, he will show up at your place, shake you down, and you will lose condition.)

After another 4 cycles, go to Kompressor Club, and Ethan will find out that the bounty contract was cancelled and get run out of the bar.

After another 8 cycles, he will show up at your place again, saying that he needs your help to pay off his debt to Kompressor Club. The countdown will also begin (viewable at your home) that gives you 24 cycles, which is plenty of time.

At the Kompressor Club, complete either Endure action "Work the Back" and/or Engage action "Work the Front" enough times to fill the "Ethan's Debt" wheel. (Positive outcomes on "Work the Front" count for two wheel sections.) Once you fill the wheel, he then asks you to steal his gun back from the bar. Do so (you can get negative outcome on this critical action dice roll, the outcome is exactly the same), and long story short Achievement unlocks after the last story bit.

Missable as Ethan disappears if you disable your tracker before finishing his tasks.

Follow the Ethan storyline and work to pay off his debt at the Kompressor bar then a pretty awesome and violent scene ensues. This is not an ending and the game will continue.

Not sure if paying his bar tab prior is required for this or that any dialogue options in between makes a difference in the outcome, but paying his tab once (58 Cryo) at least earns you a fairly early upgrade point. Make sure to pay him on the first day it is due, waiting until the second day triggers a scene when you wakeup which fails the bar tab drive and can lose you more cryo and some condition as well.