This article argues for a redefinition of difficulty in relation to the inextricable violence of modernity and examines the consecutive challenge to notions of understanding and interpretation — of a text, of language or of the other — that this repositioning brings. To this end, the article offers a nuanced rereading of Steiner’s canonical fourfold categorization of difficulty, in dialogue with, first, Édouard Glissant’s opacity and, second, Jonathan Pugh and David Chandler’s theorizations of ‘abyssal thought’, an approach emerging from Caribbean and critical Black studies, exploring the key challenge it poses to forging an unmasterful, after Julietta Singh, comparative literary practice. With an equal attention to the theoretical and pedagogical dimensions of reading difficulty, the article emphasizes the importance of the accretive and embodied nature of the reading process and offers a repositioning of textual difficulty, as a meeting site of opacities, and a reformulation of a difficult, unmasterful reading practice, after catastrophe and with others.