This paper proposes a framework for a virtual classroom application based on a Virtual Collaboration System (VCS), which is being developed under the VISNET II Network of Excellence (NoE)1, and discusses adaptation technologies that enable seamless access to classroom sessions while intellectual property and digital rights are managed. The proposed virtual classroom framework enables academic institutions to conduct their collaborative lecture series, to which registered students will be able to attend remotely and interactively over the Internet. Furthermore, the general public may also follow the classroom sessions under certain restrictions imposed by the participating institutions. In order to facilitate seamless access to a heterogeneous audience that is composed of users with various preferences and privileges accessing the classroom sessions over different network infrastructures and using terminal devices with diverse capabilities, context-aware content adaptation is required to meet constraints imposed by the usage context and enhance the quality of the user experience. Thus, this paper describes the concepts and functionalities of a context-aware content adaptation platform that suits the requirements of such multimedia application scenarios. This platform is able to consume low-level contextual information to infer higher-level contexts, and thus decide the need for and type of adaptation operations to be performed upon the content. In this way, it is aimed to meet usage constraints while also satisfying restrictions imposed by the Digital Rights Management (DRM) to govern the use of protected content.