Political and technical concerns are tightly intertwined in the design of modern space systems. The political environment often responds harshly to the associated high costs of these endeavors. Political sustainability is therefore at least as important as the technical performance parameters of new space systems under development. This paper outlines a methodology by which a system architect may trace the recursive impacts of political choice on technical choice, and vice versa. Using the implementation of the Vision for Space Exploration as a case study, a Policy–Technology Feedback loop is outlined. This paper then demonstrates how political sustainability may be incorporated into the design process such that a politically savvy system architect may appropriately trade present costs against future costs.