The story I specifically remember was called (I think) 20?S or 20QS. It was about someone who had written a computer program that could play 20 questions. I think it was written by the child of a professional computer programmer, and the father was blown away that it actually worked.
The twist was that the kid looked at the last letter of the question and if it was an "e" or some other letter, answered Yes; otherwise no. The theory was that no one would waste a question they already knew the answer to, so in this way they'd never get caught.
I believe it was in a collection of short stories, all about tech, SF and computers. I seem to recall it was connected with Creative Computing magazine, but all of the Amazon & Google searching I've done around this was to no avail.
Does anyone have any ideas or leads on where to look?