This paper aims to approach the notion of writing in the digital age in order to reflect on the question of technodiversity, or the multiplicity of cosmotechnics. It takes off with what seems to be two criticisms against each other: one from Derrida’s Of Grammatology, where he claims that ‘the notion of technics can never simply clarify the notion of writing’; and the other from Stiegler’s Discretising Time, where he openly criticized Derrida, ‘I think that Derrida unfortunately has never really explored the condition of the history of the supplement’. The essay elaborates on the contexts of these claims and suggests that this ‘indirect’ debate could be read as a parallax concerning the diversities of writing, one horizontal and the other vertical. Derrida, this essays argues, through his setting up of opposition between Hegel and Leibniz, Western phonogram and Chinese pictogram, substance and relation, proposes a diversity of writings which cannot be reduced to each other; while Stiegler by outlining a history of grammatisation, from literal, to analogue and now digital writing, proposes that philosophy has to be rethought according to this history and its respective technological conditions. This essay proposes synthesizing Derrida and Stiegler’s claims to reflect on the future of technodiversity.