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How do domestic constraints influence government behavior during military crises? Existing research typically finds that domestic interest groups recognize the costs of war and that democratic leaders eschew risky conflicts out of fear that constituents will penalize them if the country incurs significant losses. In contrast, I argue that leaders also face domestic penalties for failing to escalate popularly-supported crises. As a result, domestic accountability mechanisms can encourage democratic leaders to behave more aggressively than leaders who are unconstrained. I provide empirical support for the theory by analyzing international territorial exchanges from 1816 to 2014. When threatened by strong opponents, democracies are significantly less likely to concede territory peacefully than are autocracies. Instead, democratic leaders consistently fight—and ultimately lose—highly asymmetric wars that autocratic leaders are able to avoid. The results challenge the established view that democracies select only into conflicts that they expect to win. Instead, the evidence suggests either that democracies are significantly worse than other states at predicting the likely outcomes of war or, alternatively, that domestic constraints systematically inhibit democratic leaders from accepting favorable settlements and compel them to fight riskier, more lopsided wars than their autocratic peers. I provide further support for the mechanism by examining the decisions made by Chilean, Peruvian, and Bolivian leaders in the prelude to the War of the Pacific.