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