Business and IT practitioners, researchers, and consultants have been asking for an effective tool to assess IT-business alignment. Until now, none was available. This chapter introduces the strategic alignment maturity assessment. This assessment tool is based on the authors’ research and consulting experience that identified the major enablers and inhibitors in the achievement of business-IT alignment and the methodology that leverages the most important enablers and inhibitors. Alignment focuses on the activities that management performs to achieve cohesive goals across the IT (information technology) and other functional (e.g., finance, marketing, H/R, manufacturing) organizations. Therefore, alignment addresses both how IT is in harmony with the business, and how the business should/could be in harmony with IT. Alignment evolves to a relationship where IT and business adapt their strategies together. Achieving alignment is evolutionary and dynamic. IT requires strong support from senior management, good working relationships, strong leadership, appropriate prioritization, trust, and effective communication, as well as a thorough understanding of the business and technical environments. Achieving and sustaining alignment demands focusing on maximizing the enablers and minimizing the inhibitors. The purpose of this chapter is to discuss an approach for assessing the maturity of the business-IT alignment. Once the maturity is understood, an organization can identify opportunities for enhancing the harmonious relationship of business and IT.