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.
Know all favorites.
Complete Episode One.
Show the rebellious side.
Complete Episode Two.
Complete Episode Three.
Complete Episode Four.
Complete Episode Five.
Show the peaceful side.
See no crime in buying a bottle.
Avert catastrophe.
Allow catastrophe.
Don't read minds.
Repay the debt.
Administer justice.
Forgive a crime.
Keep quiet about the intention.
Make an unlawful arrest.
Don't bother the law.
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.