The aim of this paper is three-fold. Firstly, to briefly set out how strategic choices made about theorising about intentionality or content have actions at a distance for accounting for delusion. Secondly, to investigate how successfully a general difficulty facing a broadly interpretative approach to delusions might be eased by the application of any of three Wittgensteinian interpretative tools. Thirdly, to draw a general moral about how the later Wittgenstein gives more reason to be pessimistic than optimistic about the prospects of a philosophical psychopathology aimed at empathic understanding of delusions.