Drawing on previous work on the role of the media in the democratization processes of the Lusophone African countries (Angola, Cape Verde, Guinea-Bissau, Mozambique, and São Tomé and Príncipe), this chapter addresses the challenges and paradoxes of conducting comparative research focused on contexts where there are constraints to democratic development (although at different levels and gradation), and on which reliable information on key indicators is often missing. These are societies with different cultural expectations of democracy and political leadership, which do not fit neatly into most Western world conceptualizations. The research looked into the news media functions in democratization contexts and the role that different types of media, including new media technologies, have in creating and supporting the necessary conditions of democracy and in shaping the type of democracy that is actually being built. Finally, by examining the relation between media and politics and the dynamics of media, political, and social change, the research outlines the most important media uses and effects in these democratization contexts.