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.
Complete Episode Five.
Uncover the truth.
Find out who is there.
Choose the simple answer.
Reunite a couple.
Complete Episode Four.
Don't bother the law.
Complete Episode Three.
Repay the debt.
Keep quiet about the intention.
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.
Don't read minds.
Know all favorites.
Administer justice.
Forgive a crime.
Make an unlawful arrest.
Pick up what was left behind.
Win the war.
Make Thought crimes.
End a career.