Nowadays, more and more universities are choosing to use technological platforms to administer educational processes and to facilitate the administrative tasks that students have to fulfill. However, these changes have consequences and can generate numerous difficulties with implementation as well as student resistance. At a Belgian university that confronted such problems, an observatory of students’ uses of computer-based tools was created. This observatory has multiple missions: to characterize actual students’ use of a learning management system, to identify satisfaction factors, and to provide recommendations in order to improve the user experience. To achieve these missions and to be consistent with the current research in the field of technology acceptance, several methodologies (focus groups, usability tests, and online surveys) are used. In this article, special attention is given to users’ characteristics with regard to information and communication technology (ICT) usage and to the technology acceptance model proposed by Wixom and Todd (2005). This model is particularly relevant in the case of an observatory studying learning management systems, satisfaction, and technology acceptance. Indeed, it combines two major approaches of technology use: the satisfaction approach and social acceptance of technology approach. Moreover, it has the advantage of putting forward the distinction between the system that ICT departments control and the information that other university departments have released on the system. The results showed that the students mentioned having good competence in the use of ICT tools and that the usability difficulties they encountered and dissatisfactions they expressed can be attributed primarily to the system used and secondarily to the information presented on this system. Both factors negatively influence the intention of using the system. More precisely, regression analysis indicated that reliability, flexibility, integration, aesthetics, and available features influence the perceived system quality, while completeness, accuracy, relevance, comprehensibility, and currency of the information presented on the system influence the perceived information quality. The creation of such an observatory allows one to simultaneously study users’ acceptance and satisfaction, to differentiate the impact of personal and technical factors, and to consider the evaluation processes of technological usage at the university.