Here is the full list of all 27 Orwell: Keeping an Eye On You achievements. It takes around 8-10 hours to unlock all of the achievements on Windows.
End a career.
Find out who is there.
Administer justice.
Set Thought free.
Uncover the truth.
Make an unlawful arrest.
Win the war.
Forgive a crime.
Don't read minds.
Allow catastrophe.
Show the peaceful side.
See no crime in buying a bottle.
Make Thought crimes.
Complete Episode Five.
Choose the simple answer.
Reunite a couple.
Complete Episode Four.
Pick up what was left behind.
Don't bother the law.
Complete Episode Three.
Repay the debt.
Keep quiet about the intention.
Complete Episode Two.
Avert catastrophe.
Know all favorites.
Complete Episode One.
Show the rebellious side.