Automation in architectural design and documentation has often been a siloed process where discrete parts are scripted while other production is organized by analog documentation procedures. A made-to-measure, direct-to-drawing process provides an alternative model, leveraging the embodied expertise of skilled trades through digital automation of design and measured drawings. As a practice that questions relationships between digital processes and building, SHoP Architects pursued the joint application of craft knowledge embodied by established trades with computational intelligence manifested through automation in the design of the WAVE/CAVE Pavilion in Milan. With WAVE/CAVE as a case study, this paper explores the precedence, context, and procedures associated with automation of fabrication and material knowledge in design and drawing production, demonstrating a bridge between analog craft and digital scripting through made-to-measure automated drawing.