Many systems undergo significant architecture‐level change throughout their lifecycles in order to adapt to new operating and funding contexts, to react to failed technology development, or to incorporate new technologies. In all cases early architecture selection and technology investment decisions will constrain the system to certain regions of the tradespace, which can limit the evolvability of the system and its robustness to exogenous changes. In this paper we present a method for charting development pathways within a tradespace of potential architectures, with a view to enabling robustness to technology portfolio realization and later architectural changes. The tradespace is first transformed into a weighted, directed graph of architecture nodes with connectivity determined by relationships between technology portfolios and functional architecture. The tradespace exploration problem is then restated as a shortest path problem through this graph. This method is applied to the tradespace of in‐space transportation architectures for missions to Mars, finding that knowledge of pathways through the tradespace can identify negative coupling between functional architectures and particular technologies, as well as identify ways to prioritize future technology investments.