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.
Complete Episode Five.
Make Thought crimes.
Choose the simple answer.
Uncover the truth.
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.
Allow catastrophe.
Know all favorites.
Complete Episode One.
Show the rebellious side.
Show the peaceful side.
See no crime in buying a bottle.
Avert catastrophe.
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.
End a career.
Set Thought free.