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.
Complete Episode Five.
Reunite a couple.
Uncover the truth.
Complete Episode Four.
Pick up what was left behind.
Don't bother the law.
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.
Show the peaceful side.
Allow catastrophe.
Don't read minds.
Know all favorites.
Administer justice.
Forgive a crime.
Keep quiet about the intention.
Make an unlawful arrest.
Win the war.
Choose the simple answer.
Find out who is there.
End a career.
Set Thought free.