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