What prompts people to engage in political activities that are extremely risky? This question has inspired a myriad of political science works on contentious mobilization and revolutions, the formation of rebel movements and violent insurgencies, and individual actions against coercive, authoritarian regimes. This paper contributes to a scholarly discussion on the most effective predictors of high-risk individual action that has circulated around two sets of arguments: individual grievances vs. opportunities for collective action. Drawing on empirical insights into the Syrian civil war, we are interested in discussing this question in the context of individual military insubordination. Our empirical subject is particularly valuable for studying the effectiveness of grievances and opportunities as drivers of high-risk action, because the focus on army deserters allows us to account for individual action rather than collective action. The latter is in the center of inquiry when studying rebel formation or contentious mobilization. Second, desertions from the Syrian army have proved to be associated with extreme forms of punishment for those who attempted but failed to walk away from their units, including summary executions. Hence, using military insubordination during civil war in a repressive authoritarian regime serves as a valuable prism through which to study those factors effectively triggering individual high-risk action.