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The purpose of this paper is to examine how ICT development is progressing and what kind of political and social effects have been occurring (or could occur in the near future) in Middle Eastern Arabic countries. To examine this theme, this paper will adopt the Syrian Arab Republic as a case. To understand the Syrian government’s policy toward the ICT development, it is necessary to examine the domestic political situation, since they are closely related. Under the Bashar Al- Asad’s regime, we can confirm several reasons why they have to move forward on their ICT development policy and why it has become a crucial issue, which they cannot evade, as they had done under the previous regime, Hafez Al- Asad’s regime. The situation that the Syrian government is facing right now is known by the term, “Dictator’s Dilemma”. This paper tries to provide bases in order to examine and explore this dilemma in Syria. Also, when we examine ICT development in Syria, it is important to consider the ICT support policies, which are mainly conducted by OECD countries and international organizations and stem from the issue of “Digital Divide”. This is why international assistances could have great effect on ICT development in Syria. As a provisional conclusion of this paper, I will summarize how we can understand the current situation of ICT development in Syria, and I will also comment on the future prospect of the dilemma that the Syrian government is facing at the present time.