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.
Complete Episode Five.
Set Thought free.
Choose the simple answer.
Uncover the truth.
Complete Episode Four.
Make an unlawful arrest.
Complete Episode Three.
Repay the debt.
Don't read minds.
Complete Episode Two.
Avert catastrophe.
Complete Episode One.
Show the rebellious side.
Show the peaceful side.
See no crime in buying a bottle.
Allow catastrophe.
Know all favorites.
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.
Find out who is there.
Make Thought crimes.
End a career.