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.
See no crime in buying a bottle.
Allow catastrophe.
Administer justice.
Forgive a crime.
Pick up what was left behind.
Make an unlawful arrest.
Win the war.
Set Thought free.
End a career.
Uncover the truth.
Find out who is there.
Make Thought crimes.
Complete Episode Five.
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.
Don't read minds.
Complete Episode Two.
Avert catastrophe.
Know all favorites.
Complete Episode One.
Show the peaceful side.
Show the rebellious side.