The following comparative case study of Iraqi Kurdistan and Democratic Federation of Northern Syria-Rojava seeks to fill a gap in literature on the viability of democracy in cases of de facto statehood. There is yet to be an assessment of the potential influence of support from patron states on the degree to which democratization in de facto states is possible. This research expands upon on the argument that the decision to recognize de facto states is at least partially dependent upon the national interests of influential third party states. Syria Rojava has relied heavily on the strength of its internal sovereignty for survival where Iraqi Kurdistan received significant external support in vital phases of the state building process and was not reliant entirely on the strength of its internal unity. Where Kurdistan received essential major power support from permanent UN Security Council members early in the state-building process, as well as afterwards in constructing a divided system of governance, Syria Rojava has received little external support and faces an international community that denies its existence. It is estimated that in the following research the support of Major Powers early in the state-building process fundamentally changes the nature of internal sovereignty. More specifically the strength and weakness of conditions of internal sovereignty influence the type of governance that is practiced in the cases under analysis. Where the conditions of internal sovereignty are strong, the viability for democratization decreases; where the conditions of internal sovereignty are weak, the viability for democratization increases. In the case of Iraqi Kurdistan, the relatively weak conditions of internal sovereignty, while resulting in conditions that are more conducive to democratization, subjects the region to increased dependence on external powers for survival. Whereas in Syria Rojava, the relatively strong conditions of internal sovereignty while resulting in conditions that are less conducive to democratization, subjects the region to less dependence on external powers for survival. Theories that seek to affirm the possibility of democratization in de facto states have so far eschewed consideration of the military and diplomatic support of patron states in the early de facto state building process. There is a need for research that takes into consideration the specific events that lead to the creation of de facto states so as not to overlook the possibility that external actors play a role in shaping conditions of internal sovereignty.