This project documents the progress of research developed to explore the unique relationship between building form and urban context with the application of a novel auto-generative modeling process incorporated into a speculative design methodology. The techniques and parameters for the project are reviewed relative to key concepts of D’Arcy Thompson’s dynamic “theory of transformation” and the development of the auto-generative modeling process. This is followed by a detailed discussion of the set of exchanges between the urban context (field of influence) and the formation of the building intervention that were subsequently mappedthrough a series of diagramming studies. Specific issues explored in the project focus on Thompson’s descriptive analysis of form as a “diagram of forces” and his use of flexible, deformable topological Cartesian nets (Method of Coordinates) to subject the stasis of geometric types to dynamic transformation. Some preliminary interpretations of the project results are evaluated through studies of the generative schemes deployed in different urban situations. The initial results of the study are demonstrated with a resultant schematic building design for a modest scaled intervention in the city of Miami.