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This thesis establishes a framework for evaluating automated configuration management tools for use in high assurance software development projects and uses the framework to evaluate eight tools. The evaluation framework identifies a dozen feature areas that affect a high assurance project team's ability to achieve its configuration management goals and evaluates the different methods that existing tools use to implement each feature area. Each implementation method is assigned a risk rating that approximates the relative risk that the method adds to the overall configuration management process. The tools with the lowest total ratings minimize risk to high assurance projects. The results of the evaluation show that although certain tools are less risky to use than other tools for high assurance projects, no tool minimizes risk in all feature areas. Furthermore, none of the existing tools are designed to leverage high assurance environments--i.e. none run on operating systems that have themselves been evaluated as meeting high assurance requirements. Thus, high assurance development projects that want to leverage the benefits of configuration management tools and achieve a sufficiently strong configuration management solution must employ existing tools in a protected environment that specifically addresses the risks created by the tools' implementation methods.