Many familiar debates in STS, philosophy, and communication and information studies revolve around the relationship between formal rules, plans and instructions, and the situated actions performed in (or out of) accord with them. Of particular interest is the “gap” between formal instructions and the contingent production of such actions. A question that has long been debated is whether technological innovations can ever close that gap. This chapter will briefly review such debates, but it does not aim to resolve them. Instead, the aim is to examine how the gap is reconfigured when instructions and directions are conveyed through different media, with particular attention to digital devices such as hand-held or windshield mounted Global Positioning System (GPS) devices and applications. The chapter draws upon cases of navigation on foot or in automobiles performed with different navigational aids in familiar and unfamiliar environments. The discussion of these cases focuses on wayfinding trouble, including the experience of being lost, and also on the environmental resources (such as older means for getting directions, and legible infrastructures) for repairing a journey in the face of such trouble. The exercises suggest that the GPS does not eliminate or close the gap between directions and situated navigation, as it becomes a contingency for generating distinctive ways to get lost, even while it precludes other ways of getting lost. Readers are invited to take up variants of the exercises discussed in this chapter, and to use the chapter as a field guide for further explorations.