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.
Complete Episode Four.
Don't bother the law.
Complete Episode Three.
Repay the debt.
Complete Episode Two.
Avert catastrophe.
Complete Episode One.
Show the rebellious side.
Complete Episode Five.
Show the peaceful side.
See no crime in buying a bottle.
Allow 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.
Choose the simple answer.
Reunite a couple.
Uncover the truth.
Find out who is there.
Make Thought crimes.
End a career.
Set Thought free.