But it won't ever have trouble, because it's not trying to understand the sentence. It will tell you the most probable parsing of that sentence based on its model, whether or not it makes sense to a human.
It's almost purely syntactic reasoning. Searching these spaces of possibilities is something which, you would think, a "natural language parser" ought to be doing to earn its name.
Nobody actually knows what it means "to buffalo" something; it is not necessary to know. People solve the parse in spite of knowing that there is nothing to understand in the sentence.