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