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.
Administer justice.
Keep quiet about the intention.
Allow catastrophe.
Show the peaceful side.
See no crime in buying a bottle.
Complete Episode Five.
Set Thought free.
Choose the simple answer.
Uncover the truth.
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.
Don't read minds.
Forgive a crime.
Don't bother the law.
Win the war.
Reunite a couple.
Find out who is there.
Make Thought crimes.
End a career.