16 Leonidis, A., Korozi, M., Nikitakis, G., Ntagianta, A., Dimopoulos, A., Zidianakis, E., Stephanidi, E. & Antona, M. Technologies 2020, 8(4), 66 2020 The proliferation of Internet of Things devices and services and their integration in everyday environments led to the emergence of intelligent offices, classrooms, conference, and meeting rooms that adhere to the paradigm of Ambient Intelligence. Usually, the type of activities performed in such environments (i.e., presentations and lectures) can be enhanced by the use of large Interactive Boards that—among others—allow access to digital content, promote collaboration, enhance the process of exchanging ideas, and increase the engagement of the audience. Additionally, the board contents are expected to be plenty, in terms of quantity, and diverse, in terms of type (e.g., textual data, pictorial data, multimedia, figures, and charts), which unavoidably makes their manipulation over a large display tiring and cumbersome, especially when the interaction lasts for a considerable amount of time (e.g., during a class hour). Acknowledging both the shortcomings and potentials of Interactive Boards in intelligent conference rooms, meeting rooms, and classrooms, this work introduces a sophisticated framework named CognitOS Board, which takes advantage of (i) the intelligent facilities offered by the environment and (ii) the amenities offered by wall-to-wall displays, in order to enhance presentation-related activities. In this article, we describe the design process of CognitOS Board, elaborate on the available functionality, and discuss the results of a user-based evaluation study. https://doi.org/10.3390/technologies8040066