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The Air Force (AF) needs an evolving software tool for guiding decision makers through the complexities of software outsourcing. Previous research identified specific outsourcing strategies and linked them to goals and consequences through a variety of relationship rules. These strategies and relationship rules were inserted into a decision support tool. Since that time, more historical data and outsourcing literature has been collected thus necessitating an update to such a tool. As the number of software outsourcing projects are completed, the AF must capture the outsourcing decision experiences which guided the projects and their outcomes. In order to efficiently incorporate this new experience, the decision tool must be redesigned to allow the additional knowledge to be added in such a way that the decision rule base is automatically updated. With this new feature, the tool would increase its precision of predicting software outsourcing success as the software outsourcing knowledge evolves. Capturing software outsourcing as knowledge instead of raw information will help guide decision makers down paths proven to succeed staying clear of risks that historically plagued software outsourcing projects of the past. Software outsourcing decision makers desire not only a characterization of past experiences and predictions of future outcomes, but also reasons to help them make informed decisions.