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The Weak vs. Strong AI debate is certainly a philosophical matter. Even if we one day do have AI's that are indistinguishable from humans, there will no doubt be a debate on whether those AI's really "understand" what they're doing.
Like you said, this gets back to the Chinese Room idea.
Well, yes, it does. The Chinese Room Argument, IMO, isn't compelling in the least. There's no reason why we cannot say that the whole system is intelligent. Focussing on the guy inside the box is a canard. After all, something intelligent had to set the system up, produce the book etc.