Warning: This review contains some pretty heavy spoilers.
For those that don't know, a red herring is somthing used to throw someone off the trail of somthing. A red herring is also a picled fish, and was used to throw off scent-traking dogs.
Now, about the Machines statement in 9/10, the yes//yes//yes//probably are in fact answers, to the four questions before that.
1. Smugness IS a revelant clue.
2. It IS a red herring.
3. The Machine DOES know what a red herring is.
4. You probably know what a red herring is.
Since the Machine THINKS smugness is a revelant clue, and it ALSO thinks it is a red herring, there is the contradistion.
About the game: It was awsome, the fact that some answers were hidden didn't give me too much trouble. It would have been nice for the "Brain" to give better hints, say, every 10 or so minutes that you've been stuck.
Music fits the game pretty well.
I hope there is a sequel.