While scholars have considered the role of courts in authoritarian regimes generally, less attention has been paid to judicial-military relations. In this article I consider how courts are militarized and made subordinate and loyal to military rule. In military regimes, the courts are at risk of militarization and the process of rendering judges loyal to the military through practices such as career path socialization, selection, and restructuring of the courts. This raises an entry-exit dilemma for judges. The dilemma lies in the fact that if judges committed to civilian rule do not join the bench, they are potentially leaving the judiciary to military partisans with little prospect for reform. Yet joining the judiciary means the danger of being co-opted and adding legitimacy to the military regime or the risk of being forced out if politics shifts from civilian to military rule. Through a case study of judicial profiles in Myanmar, I explore how the loyalty of judges to the military depends on whether they are military insiders, military affiliates, civilian affiliates, or civilian outsiders. The case of Myanmar is a vivid reminder to scholars of judicial behavior that in military authoritarian regimes, judges face an entry-exit dilemma.