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