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