A clear breach of authoritarian rule within the Arab world in 2012 manifested in public uprisings among significant sectors of society. As a relatively autonomous institution within the authoritarian system of rule, the military played an essential role. In many cases, the militaries in the Arab world aligned themselves with resilient protestors or fractured, thereby easing the end of the authoritarian status quo. Though the end result is still undecided with unprecedented changes in the making, future relations between civilians and armies will be a critical factor. After authoritarian regimes collapsed but before democratic regimes are strongly established, new civilian leaders struggle to diminish the military’s ability to directly determine the course of events. This article also draws on theoretical reflections and experiences from earlier transitions to democracy witnessed in Latin America, Southern Europe, and Eastern Europe, in order to provide a reliable map of ways the Arab world might travel, as well as the tools for diagnosing the situation. Finally, this article reflects on what may be necessary to establish democratic civil–military relations in a moving Arab world.