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This article aims to investigate some aspects of the relationship between design and materiality within the field of digital material production. Following a historical perspective, the article associates the conceptual and technical foundations of digital tooling with the rise of a representational and geometric understanding of design, originating from the invention of the modern architectural project during the Renaissance. By analyzing the digitization of the industrial sector during the second half of the twentieth century, we argue that while the increasing streamlining of today’s workflows seems to bring designers closer to matter—a notion expressed by the idea of “digital craftsmanship”—, digital design tooling paradoxically originates from the project of absorbing materiality into issues of representation. The last part of the article offers an introduction to a series of contemporary practices within architecture and design, hinting at a shift toward a performative (rather than representational) approach to digital technologies.