The rapid establishment of third generation distance learning environments, the so-called Web-based or tele-teaching environments, brought some problems with it. The main means for the delivery of the new educational approach is the World Wide Web, and there are some good reasons for it: It is easily accessible by many groups of learners. It supports multiple representations of educational material and various ways of storing and structuring this information. It is powerful and easy to use as a publishing medium. Additionally, it has been widely accepted that the hyper-medial structure of the Web can support learning. Some researchers characterize the Web as an active learning environment that supports creativity. In addition to this, the Web encourages exploration of knowledge and browsing, behaviors that are strongly related to learning. The associative organization of information in the Web is similar to that of human memory, and the process of information retrieval from the Web presents similarities to human cognitive activities (Tselios, Avouris, Dimitracopoulou, & Daskalaki, 2001). However, a hyper-medial space, like the Web, cannot be considered, only by these features, as an effective tutoring environment. It is rather more appropriate to think of the Web as a powerful tool that can support learning, if used in an appropriate way. This is because learning is a process (Duchastel, 2001) that depends on other features, such as learner’s motivation, previous experience and learning strategies that the individual has been supported to develop, and so forth. Effectiveness of any educational environment cannot be considered independently of these aspects.