In the designing of urban infrastructure—its physical, economic, social, and biological systems and abstract geometric rule sets—one must consider the evolution of technology and its appropriations and applications. At issue is less the terminology or classification of, for example, explicit, top-down, parametric or algorithmic, and bottom-up, than an understanding of these as an amalgamation and paradigmatic shift in the practice of urban design (Kuhn 1996). 1 How to best “plan” for the present and near-term future of design in the age of infinite computing and the algorithm is the critical question. The position taken is simply that ostensibly we are just at the cusp of a paradigm shift which will finally enable the design and planning of large-scale urban infrastructure to embrace both top-down parametric design exploration and correlation with multi-agent systems and the exploration of emergent behaviors in highly complex and coupled dynamical systems. In short, as designers of the cities of the future we will be able to more accurately and with more formal ingenuity and confidence break down the monotony and homogeneity of twentieth-century planning tropes and begin to engender, harness, and enable urban vitality through an incorporation of emergent and intelligent intricacy, heterogeneity, and urban fluidity, as modeled and tested through both generative and parametric processes.