This is a story of the possibilities created by connection but also of the inherent fragility of movement within a network. It uses a case study of roads in ancient Japan (defined as late seventh through early ninth centuries) to show how networks not only amplify interaction but also isolation. This article explores the religious implications of road construction, both how a newly connected society enabled the rapid diffusion of a religious tradition and how increased mobility necessitated new practices. In short, I will take up “connectivity and its discontents,” a phrase borrowed from Sherry Turkle, the psychologist and scholar of technology. In doing so, I will make a historical contribution by demonstrating how roads brought Buddhism to a wide population in Japan much earlier than previously supposed and a theoretical one to uncover the religious implication of the dually connective and separative nature of networks.