This chapter provides a situated analysis of an architectural research team engaging in prototype driven experimentation. These experiments are meant to both expand the researcher's own understandings of design as well as contribute to ongoing debates in the field of architectural research and education. The chapter draws on video analysis of prototyping exchanges and discussions in which the researchers explore and reflect on varying digital design prototypes. The analysis highlights different communicative strategies that are used by the architects to explore both digital and non-digital aspects. It is argued that by entertaining these experimental modes of reasoning a number of new possibilities for theorizing architectural practices arise. This includes opening up a conceptual space that allows the architects to indulge in the open-ended questioning of core ideas and techniques that permeate their embodied understanding of the field of architecture. [For the complete volume, "Designs for Experimentation and Inquiry: Approaching Learning and Knowing in Digital Transformation. New Perspectives on Learning and Instruction," see ED661573.]