The Latin alphabet and Arabic script followed very different trajectories from the handwritten page to the digital screen. This paper will examine how the shape and appearance of Arabic script shifted in relation to new media technologies. It traces the continuity of scribal tradition and digital design as a dialogue between calligraphy and Arabic type design. Although the complexity of calligraphic and scribal designs was difficult to replicate during the era of moveable type, digital technologies provide the opportunity to reclaim scribal variety. Contextual software allows letterforms to shift according new inputs and pre-established parameters, and such parameters can be programmed to closely mimic a variety of scribal styles. Thus, calligraphic tradition is resituated as an important precursor to textual and graphic design. Current practitioners mine the rich visual diversity of scribal tradition as inspiration for contemporary design. But debate has arisen surrounding the modernization of Arabic type. On one side, type designers wish to simplify the appearance of Arabic type in line with modernist type aesthetics. Such designs place emphasis upon clarity, legibility, and the ability of Arabic fonts to operate within bilingual and multilingual texts. The recent Typographic Matchmaking projects, organized by the Khatt Foundation for Arabic Typography, provide one of the best examples of this approach. The project designed Arabic companion fonts that share visual consistency and font sizing with five Latin typefaces. On the other side of the divide, increasingly complex software simulates the visual complexity of scribal manuscripts. Programs such as the Arabic Calligraphic Engine (ACE) employ context and rule-based analysis in order to replicate the calligraphic line. The technology therefore preserves the visual and cultural heritage of Arabic tradition by replicating both the form of the texts as well as their content. Thomas Milo, who designed ACE and the accompanying Tasmeem software, was awarded the prestigious Dr. Peter Karow Award for Font Technology & Digital Typography for the sophistication and promise of the program. The presentation connects primary archival research with early specimens of Arabic print, as well as ethnographic and interview data with contemporary calligraphers, designers, and typographers. Tracing a line across calligraphy, modernity, and computing, this talk traces the aesthetic and technical shape of Arabic writing in a digital age. By looking to the past, we open exciting possibilities for the future of design.