An abundant literature has developed to examine the conditions under which contentious opposition emerges to oil pipeline development. In this article, we compare the process to site and permit two pipelines in Illinois – Enbridge's Southern Access Extension Pipeline (SAX) and Dakota Access' Dakota Access Pipeline (DAPL). Landowners mobilized against SAX but not DAPL despite demonstrable opposition to both projects. Moreover, DAPL generated organized resistance from landowners in neighboring Iowa. We thus seek to explain non-mobilization in a community otherwise at risk for mobilization. Drawing on in-depth empirical data, we argue that the lack of visible resistance to DAPL in Illinois is a consequence of the neoliberalized regulatory landscape in which landowners are embedded. Unless able to demonstrate that pipeline projects generate specific economic grievances – which was possible for SAX but not DAPL – landowners perceive themselves as having no capacity to resist. An inability to leverage economic grievances or noneconomic attachments as grounds for opposition forces acquiescence to energy development. Ultimately, this case seeks to assess how state-level regulatory dynamics help enable or constrain social mobilization. Our research contributes to scholarship examining the impact of fossil fuel infrastructure expansion on rural communities and raises important questions about the capacity of such communities to navigate energy (infrastructure) development in the ongoing energy transition.