‘Chance and Improbability’ is an article featuring in a peer-reviewed online journal, Flusser Studies. It focuses on the role of the improbable or unexpected in relation to art practice and discusses the impact of these concepts, drawing on the work of philosopher Vilém Flusser. Digital code and the visual representations it enables are now ubiquitous and the article attempts to excavate some of Flusser’s thinking in this respect and relate it to current practices in the field of art. The article discusses Flusser’s notion of the ‘technical image’ and that one’s role as an artist or cultural producer is to work against the tendency of machines to standardise and homogenise, to strive for the improbable as opposed to the probable. Drawing on the developing interest in Flusser’s work, it provides a resource for artist/scholars and features quotations from an unpublished Flusser manuscript, ‘Between the probable and the impossible’, from the Flusser Archive at Universität der Künste in Berlin (previously at Kunsthochschule für Medien, Cologne). The article also includes reflections on O’Riley’s bookwork, Accidental Journey.