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.
End a career.
Find out who is there.
Reunite a couple.
Uncover the truth.
Don't bother the law.
Win the war.
See no crime in buying a bottle.
Make Thought crimes.
Complete Episode Five.
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 rebellious side.
Show the peaceful side.
Allow catastrophe.
Don't read minds.
Administer justice.
Forgive a crime.
Keep quiet about the intention.
Set Thought free.