From baroque proto-cybertexts to countercultural gestures by historical avant-gardes there is a longstanding tradition of disruptive strategies by artists at the interstices of societies’ demand for order, control and functionalism. For the avant-gardes, and their multiple artistic inf(l)ections, part of the strategy had to do with radical changes in the way sensory perception came to be depicted by Modernism. Placing emphasis on the confluence of several arts and media, the innovative character of their proposals had much to do with the ways in which they were able to embrace notions representing modernity, such as “simultaneity,” “dynamics”, “motion”, as well as ideas such as the symbiosis between human and machine. For that purpose, they searched to induce estrangement and defamiliarization, namely by using seemingly functional mechanisms in order to raise awareness through loss of grasp. Taking from the idea of raising awareness through seemingly functional mechanisms, I argue that non-functional/dysfunctional digital interfaces that are part of contemporary artworks dealing with digitally-based haptic reading processes (namely, digital literature) are largely influenced by early avant-garde artistic proposals. Through its metamedial aesthetic and poetic critique of digital media, digital literature reinvents inherited strategies of subversion and disruption already explored by modernism, raising awareness in regard to the artwork’s processes of signification and affect. Seen as a variation of a rich heritage of experimentation with seemingly functional mechanisms in the arts, such strategies reenact age-old tensions between tradition and innovation, while laying the foundation for (re)new(ed) ways of reading and writing in digital multimodal environments.