Landscape architecture, landscape urbanism, and urbanism provide a number of tools, methods, and techniques for the design of the built and unbuilt urban landscape. The interplay of these techniques is left up to the designers, and the resulting range of projects associated with the terms is broad and inconsistent. This paper proposes Urban Scaffolding as a way to reconfigure existing practices into a flexible, scalable, repeatable, and compact design mechanism that simultaneously discovers and intervenes in a territory. The method was developed through design projects that focused on reconnecting the urban and natural landscape by means of topological strategies. Two of these projects will be used as examples in this paper.