The metaphysics of representation poses questions such as: in virtue of what does a sentence, picture, or mental state represent that the world is a certain way? In the first instance, I have focused on the semantic properties of language: for example, what is it for a name such as ‘London’ to refer to something? Interpretationism concerning what it is for linguistic expressions to have meaning, says that constitutively, semantic facts are fixed by best semantic theory. As here developed, it (...) promises to give a reductive, universal and non-revisionary account of the nature of linguistic representation. -/- Interpretationism in general, however, is threatened by severe internal tension, due to arguments for radical inscrutability. These contend that, given the interpretationist setting, there can be no fact of the matter what object an individual word refers to: for example, that there is no fact of the matter as to whether “London” refers to London or to Sydney. -/- A series of challenges emerge, forming the basis for this thesis. 1. What sort of properties is the interpretationist trying to reduce, and what kind of reductive story is she offering? 2. How are inscrutability theses best formulated? Are arguments for inscrutability effective in their own terms? What kinds of inscrutability arise? 3. Is endorsing radical inscrutability a stable position? 4. Are there theoretical virtues—such as simplicity—that can be appealed to in discrediting the rival (empirically equivalent) theories that underpin inscrutability arguments? -/- In addressing these questions, I concentrate on diagnosing the source of inscrutability, mapping the space of ways of resisting the arguments for radical inscrutability, and examining the challenges faced in developing a principled account of linguistic content that avoids radical inscrutability. -/- The effect is not to close down the original puzzles, but rather to sharpen them into a set of new and deeper challenges. (shrink)