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