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.
Allow catastrophe.
See no crime in buying a bottle.
End a career.
Complete Episode Five.
Choose the simple answer.
Complete Episode Four.
Pick up what was left behind.
Make an unlawful arrest.
Complete Episode Three.
Repay the debt.
Keep quiet about the intention.
Complete Episode Two.
Avert catastrophe.
Know all favorites.
Complete Episode One.
Show the rebellious side.
Show the peaceful side.
Don't read minds.
Administer justice.
Forgive a crime.
Don't bother the law.
Win the war.
Reunite a couple.
Uncover the truth.
Find out who is there.
Make Thought crimes.
Set Thought free.