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