This piece effects a critical revision of the interactions between late Foucault and the works of Thomas Pynchon through the theme of Enlightenment, a relationship far more nuanced than granted by current appraisals. Examining resistance, revolution, and the critical attitude alongside a focus on the Foucauldian sphere of ethics, this work posits Pynchon's negative and positive utopianism as a regulative idea. Reading both Pynchon's fiction and his essays, particularly ‘Nearer My Couch to Thee’, alongside Foucault's two pieces on Kant's ‘Was ist Aufklärung?’, it emerges that the divide between Pynchon and Foucault hinges more upon what we can know about ourselves and not necessarily, as has always been supposed, on who, or how, we can dominate. Pynchon's stance on revolution and resistance runs broadly in line with late Foucault's remarks on incrementalism; any change that can come about will, and should, be incremental while remaining pessimistic towards Meliorism. The narrowing of the sphere of ethics to ipseity that Foucault introduces to effectively counter the problems of agency that this entails, however, is not shared by Pynchon. For Pynchon, work upon the self is intrinsically contaminated and cannot be clearly delineated from the wider, impinging systems. With apologies to the author himself, it seems fair to say that when reading Pynchon in the Foucauldian Enlightenment tradition: we do know what's going on (to some, perhaps ingrained and inescapably limited, extent), and we let it go on, only ever imagining, in sorrow, how it could (never) be otherwise.