The rapid growth and widespread availability of technology has allowed enemies to dynamically develop countermeasures to military systems. Therefore, it is imperative that military systems be designed to account for these countermeasures. As such, technology roadmapping should be a critical activity in the acquisition of defense systems. Technology roadmaps provide a strategic vision for a system that accounts for the operational context, including evolving needs and technology changes. However, the operational context can be difficult to predict. This article suggests using wargaming coupled with combat simulation to better understand the operational context to allow for testing and refining technology roadmaps. Wargaming requires teams to roleplay friendly and enemy units to determine how each side adapts with the implementation of a new military system. Computer-based simulations can then convert the qualitative results from the wargame into quantitative metrics that further inform the roadmap. A case study is presented for a technology roadmap associated with an armored exoskeleton. Wargaming forecasted the countermeasures implemented by the enemy and the associated responses. The wargame results were coupled with models to quantitatively forecast the change in the warfighter's survivability and lethality. The wargame was then used to inform the technology roadmap.