The role of Open Source Software (OSS) in the e-learning business has become more and more fundamental in the last 10 years, as long as corporate and government organizations have developed their educational and training programs based on OSS out-of-the-box tools. This paper qualitatively documents the decision of the largest UK e-learning provider, the Open University, to adopt the Moodle e-learning system, and how it has been successfully deployed in its site after a multi-million investment. A further quantitative study also provides evidence of how a commercial stakeholder has been engaged with, and produced outputs for, the Moodle community. Lessons learned from this experience by the stakeholders include the crucial factors of contributing to the OSS community, and adapting to an evolving technology. It also becomes evident how commercial partners helped this OSS system to achieve the transition from an "average" OSS system to a successful multi-site, collaborative and community-based OSS project.