We outline four types of machine that informed Turing's investigations: the subversion machine, the improving machine, the perfect machine and the dysfunctional machine. We show how each deals with the issue of dysfunction, and argue that in design the ways that machines do not work can be just as illuminating as how they do. In this investigation we call on the reflections of the surrealists who sought the incongruity of object and context as the means to understanding the anarchical play of design