Adam Kelly has persuasively argued that Wallace’s oeuvre should be understood through the prism of New Sincerity, which is to say a late- or post-postmodernist quest to balance cynicism with a return to what Wallace called “single-entendre principles.” While the new sincerity paradigm is not without its critics, sincerity is indisputably central to Wallace’s ethical system, and its personal and authorial challenges provide some of the most compelling moments in his writing. The apparent sincerity of his authorial voice has been one of his most appealing attributes, and Wallace himself commented frequently on the fraught dynamic between author and reader, simultaneously predicated on sincerity and manipulation. This chapter traces the role of sincerity as, on the one hand, a sort of artistic telos for Wallace and, on the other, an endlessly thorny problem that springs up in every facet of contemporary life. The chapter goes on to highlight Wallace’s influence in contemporary fiction, highlighting Karl Ove Knausgaard as an author who explores similar questions.