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.
Complete Episode Five.
Choose the simple answer.
Complete Episode Four.
Make an unlawful arrest.
Complete Episode Three.
Repay the debt.
Complete Episode Two.
Avert catastrophe.
Know all favorites.
Complete Episode One.
Show the peaceful side.
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.
Pick up what was left behind.
Win the war.
Reunite a couple.
Uncover the truth.
Find out who is there.
End a career.
Set Thought free.