Abstract : Our research focuses on context-awareness in the field of Technology Enhanced Learning (TEL). The issues we addressed include the creation of models that take into account the learner's and the teacher's context to support communication and information sharing, and the design of TEL situations that promote contextual learning. Our research is organized around projects, aiming at improving e-learning and learning games. Regarding e-learning, major contributions feature the design and assessment of several models to support contextual communication among users, while directly linking their discussions to elements of context (resources, knowledge, learning or teaching activities). Regarding learning games, one significant contribution is the definition of a process for designing learning games and an authoring environment that integrates quality control tools to assist the authors. Our research approach acknowledged the importance of the end-users, their activities and their needs. Our systems are designed using an iterative and participatory approach. Therefore, we particularly pay attention to the design of the Human-Computer Interactions, so that they reflect the underlying concepts and models.