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.
Make Thought crimes.
Administer justice.
End a career.
Reunite a couple.
Don't bother the law.
Win the war.
Forgive a crime.
Keep quiet about the intention.
Don't read minds.
Allow catastrophe.
Know all favorites.
Show the peaceful side.
See no crime in buying a bottle.
Set Thought free.
Complete Episode Five.
Find out who is there.
Choose the simple answer.
Uncover the truth.
Complete Episode Four.
Pick up what was left behind.
Make an unlawful arrest.
Complete Episode Three.
Repay the debt.
Complete Episode Two.
Avert catastrophe.
Complete Episode One.
Show the rebellious side.