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.
Allow catastrophe.
Know all favorites.
Show the peaceful side.
See no crime in buying a bottle.
Set Thought free.
Complete Episode Five.
Uncover the truth.
Choose the simple answer.
Reunite a couple.
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.
Don't read minds.
Administer justice.
Forgive a crime.
Keep quiet about the intention.
Make an unlawful arrest.
Win the war.
Find out who is there.
Make Thought crimes.
End a career.