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.
Pick up what was left behind.
Allow catastrophe.
Know all favorites.
Show the peaceful side.
Complete Episode Five.
Make Thought crimes.
Choose the simple answer.
Complete Episode Four.
Make an unlawful arrest.
Complete Episode Three.
Repay the debt.
Complete Episode Two.
Avert catastrophe.
Complete Episode One.
Show the rebellious side.
See no crime in buying a bottle.
Don't read minds.
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.