Many cities are growing into "mega" land areas filled with complex terrain and populations where the U.S. military will undoubtedly have to engage. States often fail to provide basic services to some territories, leaving inhabitants disenfranchised. These gaps are then filled by social entrepreneurs, often ethnic- or religious-based civil society groups-or even organized crime syndicates-who effectively identify niche needs in the marketplace and fill them more effectively than other competitors, including traditional state authorities. Leaders of these groups maintain control through various means: including violence, coercion, and service provision, or through tribal, religious, or other cultural ties and structures. As the 21st century progresses, the role and structure of government is already evolving from the current Westphalian, nation-state-based system originating in the 17th century to one more loosely based on alternative governance structures (AGS), the form and function of which we are only beginning to understand. This phenomenon is easy to imagine in fragile states; however, as industrialized nations become increasingly polarized by economic inequality; as citizens' trust in the effectiveness and motives of state authorities erodes; and as social media tools help AGS organize and operate, they are also likely to become a greater threat to state authority in the developed world. In order to understand and predict the emergence of alternative governance, and to identify whether it represents a threat or opportunity to U.S. interests, we must develop a toolkit that can be based on existing sources and analytic methods that only need to be expanded to the city level or weighted and appropriately applied. Such foreknowledge is a force multiplier and an important non-lethal weapon for planning and operating in an urban environment, particularly one as dense as a megacity. In addition to social network analysis methods, cultural features, such as shared dialect or language, or a history of opposition to state control or of intergroup conflict, are important factors for understanding the development of AGS. More specifically, with enhanced sample sizes and updated information, measurable cultural factors can be attributed to residents of targeted megacities. These include Geert Hofstede's concepts of power distance, individualism vs. collectivism, and uncertainty avoidance. In looking at trends in urbanization, the focus is on governance and the factors directly related to it from the average citizen's perspective; in its most basic form, this includes providing security, economic opportunity, and other basic services. To this end, a number of existing indices can be applied to provide a picture of megacities of increasing importance to U.S. defense planning, including Transparency International's Corruption Perception Index, certain elements of the U.S. Institute for Peace's Fragile States Index, the Legatum Institute's Prosperity Index, and the United Nations (UN) Habitat Program's Cities Prosperity Index. These measures, along with cultural dimensions and basic demographic, political, and economic data, added to critical field-based human intelligence (HUMINT) sources, can provide a set of very basic indicators for piecing together the contextual environment in which the selected megacities exist, as well as their own prosperity and growth projections. Such an expandable toolbox would be invaluable for U.S. Army planners to provide a starting point for developing critical pre-knowledge of these locales and what is governing them.