This paper investigates a particular philosophical puzzle via an examination of its status in the writings of Wittgenstein. The puzzle concerns negation and can take on three interrelated guises. The first puzzle is how not-p can so much as negate p at all – for if p is not the case, then nothing corresponds to p. The second puzzle is how not-p can so much as negate p at all when not-p rejects p not as false but as unintelligible – (...) for if p is unintelligible, then p is nothing but scratches and sounds and does not seem apt for negation. And the third puzzle is how “not” could be anything but hopelessly equivocal if it sometimes (per the first puzzle) requires, and sometimes (per the second puzzle) precludes the intelligibility of p. The paper investigates these three puzzles, their respective structures, and their relations to each other. The second puzzle is expounded as the centre of gravity, and in countering two objections to the threefold puzzle, a special predicament is expounded with regard to the second puzzle’s concern with unipolar propositions – propositions that do not admit of an intelligible negation. The text concludes by indicating the first steps that could potentially lead us out of the threefold puzzle. (shrink)