The Arab Spring uprisings of 2011 have shaken the otherwise seemingly well-established authoritarian regimes of the Arab world. In Tunisia, Egypt, and Libya, the uprisings resulted in a surprising and unexpected regime change. In the eighteenth century under the Ottoman influence these countries were very similar in terms of political administration, institutions, and military organization. The divergence in paths started with the European colonization at the end of the nineteenth and beginning of the twentieth centuries with each of these countries coming under different colonial rulers: Tunisia under French, Egypt under British, and Libya under Italian rule. In the post-colonial era each of these countries have experienced strong authoritarian rule with a high level of military-politicization, although the specific organizing principles of the military and security forces have varied in each country. The purpose of this paper is to explore how the level of military politicization affected regime-change in the Arab Spring period. The revolutionary outcomes have been very different in each of these countries: Egypt and Tunisia had a relatively peaceful overthrow of their reigning governments, while Libya descended into a bloody civil war that might have ended much differently had it not been for the outside intervention of the United States and the EU under the umbrella of NATO. Yet before we can understand the variation in revolutionary outcome we must explore the variation in the paths leading to revolution. This paper will argue that the differences in outcomes may be explained by exploring the differences in civil-military relations, as well as the various characteristics of the military apparatuses themselves. In particular, this paper claims that the level of politicization of the military and the degree of openness to pro-reform movements can explain the outcome of the uprisings. First it will present a typology of civil-military relations in the Middle East and North Africa. Secondly, it turns to three case-studies, Tunisia, Egypt, and Libya, in order to explore how the politicization of the military led to successful revolutions in those three cases. Finally it will comment on the possible contribution this research can provide the existing literature on civil-military relations in general, and the Arab world in particular.