Game needs to be available on Game Pass or playable via cloud for the following to work. Possibly also works on the Series S. Does not work on the One X or Series X.
This achievement was glitched for me. Figured out it was the 4K patch that was blocking the achievement. Easiest way to get around it was to delete the game and all addon from the hard drive. Play the game via cloud/Game Pass. Load up chapter select starting at the Gulag. Busted out of prison, achievement was mine!
This solution may help with other glitched achievements by going about it in a similar way.