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When citizens of autocracies vote for the dictator’s opposition or take part in contentious collective action, they take significant risks. What drives this behavior? And why do people who are normally risk averse sometimes choose to gamble politically? This paper explores the relationship between polarization and citizens’ willingness to take political risks. Using survey data from Russia where the war in Ukraine has deepened political divisions, I study risk preference reversals, building on framing and relational theories. While the first posit that risk reversals occur, and people become risk seeking, when choices are convincingly framed as losses rather than gains, the second contend that risk discounting results when strong in-group identities are activated. I consider how affective polarization shapes the political behavior of citizens through the lens of these theories, shedding light on the psychological bases of dissent in nondemocratic settings.