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