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How do people who have long enjoyed an assumption of basic human rights and a modicum of democracy respond when they suddenly find themselves living under a heavy-handed authoritarian regime? This paper attempts to understand this phenomenon by examining how Hong Kong academics have adapted to the Hong Kong National Security Law (NSL), imposed on Hong Kong in 2020 by the Chinese central government in Beijing. It aims to understand how Hong Kong academia has made sense of and responded to changes in the larger political environment, as well as the daily practices engendered by the NSL. Data draws on in-depth interviews with 20 Hong Kong academics working across the humanities and social sciences, at various levels of seniority and authority, and across almost all of Hong Kong’s eight public universities. (Interviews with another dozen or more academics are underway at the time of writing.) The project itself was initially envisioned as a way to understand the Law’s implications for academic freedom and the learning, teaching, and research environment for Hong Kong academics. While documenting these implications, the findings produced to date also speak powerfully to the personal process of adjusting to authoritarianism as a political reality in a society that once enjoyed an assumption of basic freedoms, human rights, and at least some semblance of democratic politics and regular elections. The lessons imparted tell a larger story about how, in a search for survival and a sense of normalcy, people sacrifice a multitude of freedoms they once took for granted, sometimes at the cost of much personal anguish. The paper, most broadly, reveals how people struggle to adapt to new realities when long-held democratic assumptions are challenged by a sudden shift to authoritarianism.