In today’s world, management often rely on FLOSS (Free/Libre/Open Source Software) systems to run their organizations. However, the nature of FLOSS is different from the software they have been using in the last decades. Its development model is distributed, and its authors are diverse as many volunteers and companies may collaborate in the project. In this paper, we want to shed some light on how to evaluate a FLOSS system by looking at the Moodle platform, which is currently the most used learning management system among educational institutions worldwide. In contrast with other evaluation models that have been proposed so far, the one we present is based on retrieving historical information that can be obtained publicly from the Internet, allowing us to study its evolution. As a result, we will show how by using our methodology management can take informed decisions that lower the risk that organizations face when investing in a FLOSS system.