The paper compares information security policies of two countries, Russia and Armenia. Provided the common historical past, two countries have a close cultural, historical and, partially, language basis. Moreover currently both countries tightly cooperate, particularly, in political, economic, and military fields. As cases for comparison, we choose countries – members to such international regional organizations, as Eurasian Economic Union (EEU) and Collective Security Treaty Organization (CSTO). In accordance with the Index of Democracy, Armenia and Russia are countries in democratic transition. However they have different approaches to information security – more liberal in case of Armenia and more centralized in case of Russia. We use two levels (legal and practical) to analyze cyber strategies, institutions and experience (policies) of two countries. First of all, we provide deep and comprehensive literature review on information security. The latter is performed on the following aspects of international information security: theoretical, legal, activities of international organizations, as well as Russia and Armenia positions on these issues. Second, we analyze key theoretical concepts (information security, information warfare, etc.) and approaches to them in academic and political communities. Third, we reveal basic doctrines and policy papers regulating information security policy in these states. One of the ways to evaluate information policy effectiveness is based on comparison of countries’ positions in global rankings (e.g. ITU Global Cybersecurity Index). In addition the research considers official statistics data, experts’ surveys, public opinion polls and media publications.