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 an unlawful arrest.
Forgive a crime.
Administer justice.
Keep quiet about the intention.
Allow catastrophe.
Know all favorites.
Show the peaceful side.
Make Thought crimes.
Set Thought free.
Complete Episode Five.
Find out who is there.
Choose the simple answer.
Uncover the truth.
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.
Don't read minds.
Avert catastrophe.
Complete Episode One.
Show the rebellious side.
See no crime in buying a bottle.