This paper tests design procedures for the development of complex, organic architectural forms. It illustrates a postgraduate student design process, implementing a development sequence based on the intelligent manipulation of architectural envelopes using a variety of existing modeling tools and emerging digital techniques. These stages of development respond to imposed spatial and environmental constraints. The tests began with full-scale modeling of small segments. The major constraints at this stage were spatial requirements and the physical characteristics of materials. The forms derived from the bending properties of prestressed green timber and the dimensions of shingle cladding. This was followed by digital 3D modeling using common commercial applications. At this stage initial models were derived from a traditional space requirement brief. The envelopes for these activities were then manipulated to respond to the spatial limitations imposed by surrounding buildings. This digital modeling process metaphorically “pushed the limits” as vertices of the envelope model were stretched and shifted to achieve a perceived “fit” between the two sets of spatial dimensions. The spatially manipulated geometry was then imported into Ecotect, an environmental analysis package. As an example, the envelope’s morphology and cladding material options on the acoustic qualities of the surrounding space were tested. The improved geometry was then imported into a Virtual Reality room, in which the spatial experience was simulated in presentations to the design team and potential occupants. This room utilized six projectors to create an immersive experience to users wearing stereoscopic goggles, and moving in a space surrounded by three large screens, creating a CAVE-like presentation space. Finally there was an attempt to complete the circle by returning from the simulated world to the physical worlds, by creating full-scale models from the digital geometry. This included low-cost techniques such as the generation of paper facets, and the use of more expensive rapid prototyping technology.