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