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