This article underscores the need for entrepreneurship research in extreme contexts to conceptualize the idiosyncrasies of the geopolitical dynamics under which entrepreneurs operate, and to consider the ethical implications emanating thereof. Undertaking such a task will illuminate the contextual challenges that local entrepreneurs must routinely placate, or otherwise navigate, to survive. Drawing on rich qualitative data from the Occupied Palestinian Territory of the West Bank, this paper demonstrates one avenue by which to capture the nuances of an extreme context in relation to its effects on the entrepreneurial process. Specifically, it shows how data collected at myriad institutional sites—from actors that are not only directly, but also tangentially, connected to entrepreneurship in the local market—can effectively unveil the vicissitudes of the extreme context. This article further contends that a comprehensive and a holistic understanding of the extreme context will move toward revealing the nature of political embeddedness of entrepreneurs in their institutionally unstable environment—a concern that is especially conspicuous in geopolitical areas that would qualify as being extreme.