While road safety in the United States (U.S.) has been continually improving since the 1970s, there are indications that these improvements are becoming increasingly difficult to sustain. Strategic Highway Safety Plans (SHSPs) are prepared by States to guide road safety management, however assessing the appropriateness of these plans remains a significant challenge, especially for the future in which they are to be applied. This study developed a new methodology to assess SHSPs from the perspectives of comprehensive system-based safety management and relevant future issues that can be applied before SHSPs are implemented, thereby avoiding long periods after implementation before assessing the appropriateness of the plans. A rating scale was developed and applied to assess 48 U.S. SHSPs against two key criteria: 1. a comprehensive framework for road safety, and 2. the anticipated changing, difficult and unpredictable nature of future transport and its context. The analysis concluded that current SHSPs have good national oversight with several strengths but were weak in some areas of content and did not address future challenges. Improvements are suggested to strengthen the plans thoroughness by being consistent with systems theory and practice, as well as ways that these SHSPs can be more resilient to future circumstances. Implementing the recommendations in this paper provides the opportunity to adopt a system-based safety management practice that has been successful in other hazardous industries. Doing so is expected to most efficiently and effectively continue the recent improvements to road safety, which is likely to be increasingly difficult otherwise.