Cloud computing, specifically the Commercial Cloud Service (C2S), has immense potential to advance the state of the art within the defense community and provide mission benefit in timeframes and costs previously unattainable. This paper will explore the challenges legacy programs face and how modern cloud systems, combined with industry best practices, mitigates those challenges. Additionally, it will explore how Cloud Computing empowers innovation, reduces costs, and improves system quality, if executed properly. The information is supported by Solidyn’s experience migrating a legacy application to C2S under the Seven Hills contract, providing a real-world example of how to be successful in C2S.