This chapter presents the functional and technical architecture of a recommendation system of free learning management systems that the authors have implemented to facilitate the choice of the most suitable LMS to meet the objectives, specifications, and criteria chosen by the institution. Thus, any random choice entails a loss of money, effort, and time loss for porters and device designers, and this is for various reasons (cost, utility, usability, etc.). Notably, this system takes into account more than 20 LMSs. The choice of these LMSs is based on a methodical and systemic approach that identifies the adequate criteria to the objectives and specifications chosen by the institution, depending on the objects and pedagogical tools related to the recommended teaching and learning device, to retain the most suitable LMS. This chapter is motivated by the desire to clarify and support users in their choice of the most suitable LMS to meet their needs and to get maximum benefit from the potential offered by technologies in pedagogy.