Online learning—whether it is human-facilitated or automated, hybrid/blended, asynchronopus or synchronous or mixed--often relies on learning/course management systems (L/CMSes). These systems have evolved in the past decade-and-a-half of popular use to integrate powerful tools, third-party software, Web 2.0 functionalities (blogs, wikis, virtual worlds, and tag clouds), and a growing set of capabilities (eportfolios, data management, back-end data mining, information assurance, and other elements). This chapter highlights learning/course management systems, their functionalities and structures (including some integrated technologies), their applied uses in adult e-learning, and extra-curricular applications. A concluding section explores future L/CMSes based on current trends.