Could a machine ever think dialectically? There are many ways to make this a stupid question, or to make it beside the point. You could say, for example, that even a machine that can play Chess and beat up Chess grandmasters is not really thinking Chess (cf. Searle, Dreyfuss). But I think it’s enough of a question that, to treat it properly, you have to handle it with kid gloves. You have to define its terms in such a way that it is a good question, even if the definitions are not good definitions but only barely passable ones.
Maybe it can be rephrased this way. Could a computer be programmed to manipulate symbols such that a clever drudge – someone not entirely shut away from latent dialectical possibilities, and yet not so utterly their agent that inert material also becomes the occasion for their activation – reading its outputs would be led by the nose to think dialectically?
You could say such a clever drudge is a propagandistic grey area who necessarily doesn’t exist. If so, is it for the sake of the dialectic that she doesn’t?