ABSTRACT In 1735, Leonard Euler presented a solution to the practical problem of whether a route could be plotted to cross each of seven bridges in Königsberg once. His negative solution used the simplest of mark-making strategies to resolve a conceptual problem. Euler did not actually cross the town's bridges, but used them to resolve questions of connectivity, after which diagrammatic representations can be seen as the restructuring of logical problems to allow for inductive reasoning, for fruitful application beyond theory. But what if such a working graphic has as its target something that is simply incomprehensible? What are the upper limits of the denotational logic of such diagrams? This paper presents a drawing-research project that tests the cognitive advantages of technical graphics by directly engaging with things that cannot be made easier to understand through their use.