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