This paper explains the divergent military behavior in the “Arab Spring” uprisings in Tunisia, Egypt, Libya, and Syria using thorough case studies that analyze five factors shaping military behavior: ethnic favoritism, regulated patronage, unregulated patronage, perceived legitimacy, and tactical control. Drawing on the divergence between Libya and Syria, as well as the nuanced nature of Egyptian military behavior, the paper underlines the need to embrace complexity and reject monocausal explanations, dichotomous outcomes, and unitary actors in the analysis of civil-military relations. Instead, the paper develops and advances a two-stage game tree in which the military leadership can attempt to retain, replace, or remove the authoritarian regime, and the military rank-and-file can then react to the leadership’s decision in terms of its rate of defections or its acceptance of change. Additionally, the analysis highlights the importance of the regime’s control of the military at the micro-level in determining the behavior of the military (which is so closely linked to transition outcomes) at the macro-level.