Nowadays, connectivity is practically imposed for everyone, as it is used for professional interactions, information retrieval, or just for entertainment. Thus, the importance of communicating, along with the need of people to interact through various foreign languages, increases rapidly, so as to enable ubiquitous connectivity and continuous updating. The increase of the vocabulary in a foreign language is often provided as a service in the context of web-based systems and can be significantly facilitated through considering the various ways that knowledge can be perceived and interpreted by each person. The goal of this paper is to consider such factors in designing a “cognitive, web-based, foreign language learning management system”. The system proposed is capable of monitoring the user’s activity and adapting accordingly, so as to improve the learning process as a whole. This is achieved by exploiting Bayesian Networks’ concepts, in order to monitor past preferences, acquire knowledge and estimate the likelihood of future preferences. The paper presents the related work in the field and the influences in the current work, the system’s basic requirements and structure, the methodology for introducing cognition in such a system and indicative simulation results that showcase the system’s effectiveness.