In this paper, using Mark Schroeder’s (2008a) expressivist semantic framework for normative language as a case study, I will identify difficulties that even an expressivist semantic theory capable of addressing the Frege-Geach problem will encounter in handling the logical possibility of moral dilemmas. To this end, I will draw on a classical puzzle formulated by McConnell (1978) that the logical possibility of moral dilemmas conflicts with some of the prima facie plausible axioms of the standard deontic logic, which include obligation (...) implies permission. On the tentative assumption that proponents of ethical expressivism should be generally committed to securing the logical possibility of moral dilemmas in their semantic theories, I will explore whether and how expressivists can successfully invalidate obligation implies permission within the framework developed by Schroeder. The case study eventually reveals that this can indeed be a hard task for expressivists. Generalizing from the case study, I will suggest that the source of the difficulty ultimately lies in the mentalist assumption of the expressivist semantic project that the logico-semantic relations exhibited by normative sentences should be modeled in terms of the psychological attitudes that speakers express by uttering them. My final goal will be to show that the difficulty expressivists face in dealing with the logical possibility of moral dilemmas is a reflection of the more general problem that their commitment to the mentalist assumption prevents them from flexibly adopting or dropping axioms in their semantic theories to get the right technical results. (shrink)