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.
End a career.
Make Thought crimes.
Find out who is there.
Reunite a couple.
Don't bother the law.
Win the war.
Forgive a crime.
Administer justice.
Don't read minds.
Avert catastrophe.
Know all favorites.
Show the peaceful side.
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.
Keep quiet about the intention.
Complete Episode Two.
Allow catastrophe.
Complete Episode One.
Show the rebellious side.
See no crime in buying a bottle.