New strategies for sustainability within the Department of Defense are focused on addressing present and future needs while strengthening community partnerships that improve operational abilities. This “across-the-fence line” strategic thinking requires innovative tools that can engage a broad segment of the community and a variety of military interest groups. These tools must provide a platform for understanding the challenges and realizing the goals of both private- and public-sector interests. They must tangibly represent many different potential futures, their implications, and policies that can help mobilize solutions quickly and easily in a uniform, consistent, and democratic manner. The Strategic Sustainability Assessment (SSA) consists of a series of complementary tools for forecasting and backcasting that provide regional stakeholders a unique perspective on potential sustainable regional policy and investment choices. Forecasting approaches use dynamic spatial modeling techniques to project potential future urban transformations and their implication to the social, environmental, and economic fabric of the region. Backcasting is used to determine critical sets of strategic interventions designed to offset the simulated future impacts. The results of the analysis are managed through the use of a Web-based GeoPortal. This helps to democratize the information by providing it to local stakeholders in a useable and accessible way. The hope is that greater and more direct access to models and the information they generate will help lead to better, more sustainable planning decisions in our military bases and in our communities.