In this paper I return to one of the central points of contention in the renowned debate between John Searle and Jacques Derrida with the aim of rethinking the role of success and the place of failure in communication. What is the philosophical significance of Austin's decision to exclude from his investigation (in How to Do Things with Words) certain utterances that cannot qualify as successful? Examining the conflicting ways in which Searle and Derrida understand and respond to Austin, I try to flesh out Derrida's call to grant failure (or the "negative") the important place it deserves in our understanding of speech. Yet, whereas for Derrida, the call to recognize failure as an "internal and positive condition" ultimately leads to a structural-albeit a deconstructive-critique of language's conditions of possibility, I focus instead on the implications which this insight may have for our understanding of the actuality of language. Consequently, I argue that while Derrida's critique subverts the hegemony of success, it ironically remains, like Searle, distant from and external to the actual reverberation of spoken language.