This article will present two roof-structure case studies to delineate the challenges presented by digital workflow as well as the problems yet to be solved. At least with respect to free-form wood structures, file-to-factory production is still more of a Utopian concept than a reality. Although they vary in functional and formal terms, Shigeru Ban’s Centre Pompidou in Metz and the Clubhouse in Yeoju have a number of similarities. They are both based on the same triangular grid projected onto a curved roof shell. And aside from the wood-construction firm, the same team of specialists took part in their realization. The figures for both projects are impressive. The roof at Metz encloses 8000 m² and consists of almost 1800 glu-lam beam segments – with a length of 18000 m end-to-end. A CNC milling machine fashioned the beams.