The aim of this paper is to contribute to an appreciation of the metaphilosophical significance of scepticism. It proceeds by investigating what the differing characterisations of the sceptical threat reveal about the kind of understanding that is being sought; and specifically, what this envisaged understanding connotes concerning how epistemological inquiry is itself conceived. An investigation, that is to say, into how these characterisations support or help constitute that conception of inquiry by attempting to keep a relationship with ‘the sceptic’ going on their own terms.