Content externalism is the dominant view in the philosophy of mind. Content essentialism, the thesis that thought tokens have their contents essentially, is also popular. And many externalists are supporters of such essentialism. However, endorsing the conjunction of those views either (i) commits one to a counterintuitive view of the underlying physical nature of thought tokens or (ii) commits one to a slightly different but still counterintuitive view of the relation of thought tokens to physical tokens as well as a (...) rejection of realist physicalism. In this essay I reveal the problem and articulate and adjudicate among the possible solutions. I will end up rejecting content essentialism. (shrink)