In this paper, Crispin Wright’s unified strategy against scepticism is put under pressure through an examination of the concept of entitlement. Wright’s characterisation of a generalised form of scepticism is first described, followed by an examination of the concept of entitlement and of the role played by presuppositions in his strategy. This will make manifest the transcendental structure of this response to scepticism. The paper ends with a discussion of the effectiveness of this transcendental strategy in providing a satisfying response to scepticism.