New digital technologies are challenging the traditions of the architectural design methodology, the relationship between context and design, and the dependency on skilled workmanship for the fabrication of beautiful and complex architecture. Intellectually, applications of digital technologies are also allowing for the reinvestigation, reinterpretation, and redevelopment of historical concepts, theories, and skills. Our focus of ornament in this paper is presented as a constrained architectural testing ground, a reduced issue that still addresses the primary issues of geometry, aesthetics, individualism, and the transferal of design to materiality. Our work on digital ornament combines the traditionally intuitive skills of geometric & graphic manipulations with easily edited input (variables and digital images), control through parametric programming, and automated output (CNC manufacturing).The combination of these processes allows for efficient diversity and uniqueness of design, while also compensating for the increasing cost and declining availability of skilled artisans for the physical fabrication.The presented projects in teaching, research, and professional activities demonstrate our ongoing experiments with new technologies of programmed surface modeling and computer numerically controlled manufacturing (CNC manufacturing).This work has been incorporated in real world projects, both in the revitalization historic buildings, and in new applications of ornament in contemporary architecture.