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