Although IS research acknowledges the importance of path dependence with the generalized response that "history matters," this broad understanding does not substitute for a more systematic historical analysis of how paths emerge and how technological change breaks them. In this context, we draw on the theory of strategic path dependence from organization and management research to develop a more nuanced understanding of path dependence and then explore how technological change breaks these strategic paths. Based on a narrative analysis of the strategic development of incumbents in the funeral industry, we reconstruct the core components of strategic paths-strategic patterns and self-reinforcing mechanisms- A nd scrutinize the Internet's role in breaking these paths. We suggest that technological change helps break strategic paths by destabilizing the very self-reinforcing mechanisms that led to their emergence and reproduction in the first place. Furthermore, by showing that breaking strategic paths involves a subsequent critical event that destabilizes the strategic pattern, we advance a process understanding of how strategic paths are broken. This paper thus provides much-needed historical analyses of IS-related phenomena, offers a more precise and systematic understanding of path dependence in IS research, and yields insights into the process of how strategic paths are broken.