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Over the last decade, elected leaders across a number of established democracies have sought to subvert democratic processes. These moments create a dilemma for public employees who have competing allegiances to neutral competence and protecting popular sovereignty. Some recent work has explored how public employees respond to this dilemma but, to date, few studies have focused on military personnel. This is an important omission because, historically, militaries have played an important role in determining whether democratic states turn toward autocracy. As such, this paper reports on the results of an experiment that explored how U.S. military servicemembers respond to anti-democratic leadership. It makes three basic findings. First, servicemembers responded in conflicting ways to anti-democratic presidential leadership: some remained committed to following orders while others indicated an openness to disobeying illiberal presidential orders. Second, a pro-democracy cue from a bipartisan Congress emboldened respondents to disobey unlawful orders; in contrast, a pro-democracy cue from military leaders had no effect on servicemembers’ views. Third, an exploratory analysis revealed that respondents’ answers were associated with several socio-demographic characteristics. Taken together, the results suggest that servicemembers would be divided about how to respond to anti-democratic leadership. Ultimately, their interpretation of an illiberal moment may depend upon counter-messaging from elected officials and their individual-level characteristics.