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