As the process of software development has matured, the reuse of open source software has become commonplace. Such components are commonly made available through open source software licenses, which can both provide permissions and impose restrictions regarding the software’s distribution, modification, and reuse. Modern systems can have many such licensed components, complicating the task of license compliance and compounding the risk associated with reusing open source components. To address these issues, this dissertation seeks to identify weaknesses in current processes and automated tools in order to develop new compliance tools and resources grounded in the realities of software compliance as revealed by software developers and legal practitioners.