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