The use of learning management systems (LMSs) for learning and knowledge sharing has accelerated quickly both in education and corporate worlds. Despite the benefits brought by LMSs, the current systems still face significant challenges, including the lack of automation in generating quiz questions and managing courses. Over the past decade, more attention has been accorded to analyzing the rich learning data captured by the systems and developing tools that support contemporary learning modes. This article considers a popular LMS, Moodle, and showcases four innovative projects that aim to extend the system's capabilities and address the abovementioned problems: 1) the Quiz Making Language markup system; 2) an approach to learning analytics using ad-hoc reports and artificial intelligence enabled visualization; 3) automating course administration tasks; and 4) a 4-in-1 learning application for flipped learning. These projects target all main users of the system, including instructors, learners, and administrators. It is illustrated from this study that the innovative use of web technologies and learning analytics has great potentials in improving LMS user productivity, and supporting and informing learning.