In this chapter, we look at the research area of discursion and context-aware information as it relates to the user. Much research has been done in the area of effective learning, active learning, and in developing frameworks through which learning can be said to be achieved and have some possibility of being measured (i.e., Networked Learning and Bloom’s Taxonomy) (Bloom, 1956). Having examined many such frameworks, we have found that dialogue plays a large part, and in this chapter we specifically examine dialogue in context of the user’s background and social context. This always plays a critical role, and it is around this that we want to dig deeper. We aim to provide a quality discourse analysis model which will achieve in more detail a picture of the users actual level of knowledge. Problem solving skills, together with the critical thinking capability as part of a team, and individually, in the following chapter.