The intention of this essay was to conduct two comparative analytical units called, “Most Similar System Design" (MSSD). The first unit is Somalia and the other is Iraq. The main purpose of the essay is to study deeper in Somalia and Iraq’s democratization process and also to analyse the deference’s between these two countries based on democratization-process. The essay's key questions are: How did Iraq get further into the democratization-process compared to Somalia? Why couldn't Somalia make a successful democratization process like Iraq? The essay is implemented by Dankwart A. Rustows democratization factors. The results indicated that: (i) Somalia failed in its democratization-process, due to the absence of national unity and a rapid transition. One of the main obstacles was Puntland and Somaliland which hindered the national unity of Somalia. (ii) On the other hand, Iraq was different in its democratization- process. With the support of the United States, Iraq achieved great success in the unification of Iraqi civil society the embodiment of smooth transition. (iii) Finally, the conclusion indicates that: national unity, societal norms and a rapid transition were the decisive variables.