The conceptual dyad of urban/rural has long formed the basis of the planner’s description of space. However, the terms themselves are increasingly insufficient to describe the world in which we live, presenting as overdetermined and reductive signifiers. In this photographic essay, we use Google Earth satellite images to examine a series of locations where descriptors such as ‘urban’ and ‘rural’ falter against manifold, shifting, and unstable landscape forms. We draw on Henri Lefebvre’s concept of the abstract spaces of capitalism, globalization, and urbanization, which he argued are dialectically produced through their interaction with landscape. However, where Lefebvre contended that abstraction instantiates in more or less discrete typological forms, we argue that abstract space only becomes intelligible under conditions of ‘entanglement,’ where qualities such as ‘urban’ and ‘rural’ become momentarily comprehensible at the instant we observe or describe them. In the end, holding the world still long enough to describe it reveals crucial patterns and relations, but always at a cost, always with the risk of reduction, simplification, and overdetermination. Such pitfalls are inevitable in research; however, they become all the more prevalent as the terms we use to describe the world become less and less applicable, and as the accumulation of anomalies compels us to build new models and to tell new stories.