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.
Make Thought crimes.
Make an unlawful arrest.
Win the war.
Forgive a crime.
Administer justice.
Keep quiet about the intention.
Allow catastrophe.
Show the peaceful side.
Complete Episode Five.
Set Thought free.
Uncover the truth.
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.
Complete Episode Two.
Don't read minds.
Avert catastrophe.
Know all favorites.
Complete Episode One.
Show the rebellious side.
See no crime in buying a bottle.