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 Five.
Set Thought free.
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.
Complete Episode Three.
Forgive a crime.
Complete Episode Two.
Know all favorites.
Avert catastrophe.
Complete Episode One.
Show the peaceful side.
Show the rebellious side.
See no crime in buying a bottle.
Allow catastrophe.
Don't read minds.
Repay the debt.
Administer justice.
Keep quiet about the intention.
Make an unlawful arrest.
Win the war.
Make Thought crimes.
End a career.