Traditional strategies for highway projects during the 1950s and 1960s focused on three dimensions of project management: cost, schedule, and technical (scope). Recently, with the focus shifting towards reconstruction/rehabilitation projects, project management strategies have shifted to include other project management dimensions. The Second Strategic Highway Research Program (SHRP2) project R-10 examined the best practices for managing complex renewal projects. The primary outcome of the study was a recommendation to utilize a five-dimensional project management planning (5DPM) model that added context and financing as two new dimensions to the traditional dimensions of cost, schedule, and technical. Pilot testing of the 5DPM implementation suggested that the most complicated dimension to assess during the project management planning phase for a complex project is the context dimension. Currently there is no efficient, structured process for evaluating the context dimension on complex projects within the 5DPM framework. Given this, the objective of this study is to develop a decision support framework which can be used by different transportation agencies when assessing contextual factors and assigning complexity rating scores. The framework uses a structured analytical process as opposed to the more subjective scoring used during the 5DPM workshops. As a major part of its methodology, this research uses a multiple-criteria decision-making tool called analytical hierarchy process in developing the framework. The paper presents two implementation examples which demonstrate the feasibility of the developed framework for a rebuild project and an expansion project.