This study aimed to characterize the factors affecting the entrepreneurs' decisions during the internationalization process of medium-sized firms in Syria, and to disclosure the implications of the differences about the motives and gains from working internationally through a comparison between internationalized and non-internationalized firms. The sample comprised of (35) firms in Damascus and its countryside, which are working in industrial and commercial sectors. The sample consists of (17) internationalized firms and (18) non-internationalized. The researcher has used the "descriptive analytical method" and taken of the "case study" as a procedural framework, and developed a questionnaire especially for this purpose based on scale previously applied in the study of internationalization of Egyptian companies.