On the subject of the Turing test, Sherry Turkle's Life on the Screen discusses a clever MUD bot, Julia, that fooled someone into repeatedly hitting on her; an observer of Julia's is quoted, Frankly, it's not entirely clear to me whether Julia passed a Turing test here or [the suitor] failed one.
Jaron Lanier's One Half a Manifesto observes the same:
Turing's mistake was that he assumed that the only explanation for a successful computer entrant would be that the computer had become elevated in some way; by becoming smarter, more human. There is another, equally valid explanation of a winning computer, however, which is that the human had become less intelligent, less human-like.
This ancient Salon article expresses the same sentiment about the Office agent (Had the Office Assistant learned what I wanted? Or had it forced me into its own mold -- to speak paper clip pidgin, to think paper clip thoughts?
) while Lanier goes on to complain of other "features" with which Office tries to think for people. The general idea is that very clever programmers can write tricky programs that seem smarter than actual people less swuft in the clever department:
Julia turns to the subject of hockey whenever the human communication she receives is too complicated. This causes some MUD players to perceive her as a boring or limited human rather than as a clever piece of software. Foner describes the reactions of one young woman... who originally thought Julia's limitations might be due to Down's syndrome.
And some say this cheapens humanness. That's the general topic of this part of Life on the Screen and it's pretty intriguing.