Educators are increasingly asked to design digital literacy experiences. Yet most attempts, we argue, suffer from limitations imposed by a deterministic – either social or technological – perspective, where humans and machines are assumed as competing for control and literacy is equated with mastery. In this article we propose to reconceptualize digital literacy at the crossroads between a critical approach and a postdigital perspective and show what implication it has for the design of digital literacy education. At the conceptual level, we present our distinctive understanding of a critical postdigital literacy, based on a relational ontology, a sympoietic rationality and an understanding of education as more-than-human subjectivation. At the design level, using as an example the case of a series of art-based digital literacy workshops, we show how such a conceptualization enables a particular kind of design for postdigital critical literacy practices. Through an experimental exercise in sociological fiction, we discuss how students engaged in a socio-material, bodily and aesthetics practice of critical digital literacy as experimental re-assembling. In conclusion we discuss how the perspective we experimented with offers a different way to approach the nexus between the politics of design for digital literacy education and citizenship in a postdigital world. Here literacy practices are understood as ways to nurture the capacity of heterogeneous agencies to participate in the ongoing bargaining that any postdigital assemblage demands and, relatedly, to promote citizenship as a process of becoming which involves collective and distributed participation and thinking for the common good.