The essay seeks to clarify some of the decisive but often obscured issues in the famous debate between Jacques Derrida and Jonn F. Searle. The debate commenced in 1977 with the publication in Glyph of Derrida’s lecture Signature Event Context from -71, followed by Searle’s Reiterating the Differences. A Reply to Derrida and subsequently Derrida’s reply Limited Inc a b c … which encouraged Searle to renew his criticism. I situate the debate within a philosophical context where questions of the aim of philosophy and the nature of philosophical writing cannot be excluded from the specific topics that are being discussed. Starting from Derrida’s controversial reading of Austin, where a few key points of criticism are placed under scrutiny, I proceed to problems of writing and communication where special attention is paid to the concept of iterability and Searle’s remark that this has been confounded with permanence in Derrida’s exposition. The concept of ”writing” is examined as a crux in the understanding of the two philosophers. And iterability is then found to be derieved from the theorization of absence in relation to that very concept. Iterability designates an essential possibility of absence and implies the possibility of every mark to be grafted onto new contexts of significance. Thus it draws the consequences of a general repeatability, within which difference is underscored as the inevitable outcome. The last section of the essay relates to the phenomenological project of investigating the genesis of idealization and traces the emergence of iterability in Derrida’s further writings on Husserl, where repetition can be perceived of as constitutive for ideality and thus for identity. Bearing on this observation, the type/token-distinction, proposed by Searle to undo the problem of iterability, is subjected to further inquiry and linked to the process of idealization, within which iterability is revealed to have a temporal relevance that also affects the notion of permanence. The claim is then made that iterability should be understood as a fundamentally ambiguous phenomenon through its dual relation to identity and difference. Its utility is found to be hinged upon the status of the possible. Finally, the question of iterability as concept is posed, which entails its interdependence upon notions of dissemination and différance.