The discourse on depleting natural resources and compromised environments have led to extended research on sustainable designs methods, building practices and materials. Beyond the actual performance of building products and components, research on sustainable building increasingly focuses on the long-term effects of the production, application and life cycle of building materials on the natural environment, human inhabitation and quality of life. Computer aided manufacturing technologies play a significant role not only in the transformation of design and building methods, but also in an extended discourse on cultural development. Globally available technologies connect the design and building process to a broad range of long-term ecological factors by creating a correlation between "the emergent political, economical and social processes and … architectural techniques, geometries and organization." Through this interrelationship to economy and culture, technology and its applications are also directly related to notions of place and territory as well as to fundamental ideas of ecology. The collaborative research and design study for an outdoor theater roof structure at the University of British Columbia Malcolm Knapp Research Forest at Maple Ridge, B.C., Canada, focuses on the use of digital media in prefabrication and material optimization. By utilizing small square section timber and minimizing the use of alienating connectors the research on the wood roof structure illustrates the potential of a design culture that seeks innovation in a broader understanding of ecology routed in regional culture, environmental conditions, economy and tradition. Labor intensive manufacturing techniques are redefined aided by computer controlled machines and virtual modeling of complex geometries is translated into simple operations. The result is a more sensible and accurate response to the place’s demands. In order to generate innovative design interventions that make a constructive long-term contribution to the preservation, maintenance and evolution of the environment, design needs to be based on a comprehensive understanding of its context and the distinctive qualities of the materials used. Following the example of the outdoor roof structure, this paper aims to define innovative design as work that resonates at the intersection of the fields of technology, material science, manufacturing processes, techniques of assembly and context that constitute the expanded context or complex ecology that projects need to engage. It is in design research studies like for the outdoor theater roof structure with focus on CNC wood fabrication technologies that the common design and building discourse is put to question, boundaries are explored and expanded and the collective understanding is improved towards ecological design.