This issue of the journal proposes reflections on the relationship between drawing, writing, and digital culture, considering how the early debates on computerisation, its promises, fears, and cultural disorientation, resonate today with discussions on artificial intelligence and the automatic generation of images. From speculative visions of the future to immersive digital environments and relational gardens, the volume’s essays investigate how drawing structures communication, generates knowledge, and redefines spaces of representation. Geometry, mathematics, art, and digital media converge, reaffirming drawing as a persistent and adaptive language that bridges past traditions and new paradigms.