Context Sensitive Solutions (CSS) provides a systematic and comprehensive approach to project development from inception and planning through operations and maintenance. The ability to categorize and measure the benefits of CSS projects is vital to the long-term success of this approach. The paper presents a framework for transportation officials and professionals that allows for the comprehensive quantification of benefits resulting from CSS through all phases of project development. A fundamental aspect of this framework is the identification of CSS action principles and their potential benefits. A matrix that correlates benefits to specific CSS principles was generated to allow for the development of appropriate metric indicators for each benefit. Guidelines for benefit analysis have been developed to provide transportation agencies with a set of recommended practices for assessing benefits. The guidelines emphasize the fact that CSS is a principle-driven, benefit-justified effort that can enhance an agency's goals and interaction with stakeholders and the public. The need exists to analyze and measure the benefits of CSS and its impact on projects (e.g. cost and delay) in order to demonstrate a best use of agency resources.