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