As online education programs expand across the country, many universities are adopting course management software (CMS) such as Blackboard or WebCT. Although these out-of-the-box solutions may simplify the administration of online classes, they do not comprehensively meet the needs of mature testing organizations. This chapter describes the process that has led Weber State University to reconsider whether an out-of-the-box implementation of WebCT actually is a sensible strategy.