Ambiguity is the fundamental condition of all of the narratives that constitute the oeuvre of Thomas Pynchon. This brief chapter explains and analyzes the functions of ambiguity in relation to Pynchon's use of language, techniques of characterization, and the genre of his writing. While ambiguity contributes to a frustrating interpretive experience for his readers (both intradiegetic and external), Pynchon's use of ambiguity is not by necessity negative. Ambiguity is a subversive, generative force that makes possible the resistance to fixed meanings and the liberation of semantic potentialities that are the unanticipated discoveries made by narrative protagonists that ostensibly seek a definitive ending to their hermeneutic quests.