This is the first achievement gained through the Operation Anchorage DLC.
For this you'll need to pick up the radio signal of the outcasts, I personally picked it up around the Citadel, once you've done that fast travel to the "Red Racer Factory". Head south from this location and you should come across a door called; "Door To Baileys Crossroads Metro", once in the tunnels just follow your marker while fighting through the enemies, once you've fought your way through the tunnels and you're outside you'll be greeted and continue to fight some more enemies. Eventually you'll find yourself at the Outcast Outpost, when inside head down and you'll get to speak to a bunch of people, which will in turn unlock the ability to go into the simulator, then you'll net yourself this achievement!
If you're having trouble with the quest, check out the video walkthrough below!
*Credit to MahaloVideoGames for the videos