There is a growing body of empirical evidence to suggest that users tend to make poor decisions in traditional educational systems as the navigational freedom given to the user leads to comprehension and orientation difficulties in the sense that users may become spatially disoriented, lose sight of educational objectives, skip important content, choose not to answer questions, look for stimulating rather than informative material or simply use the navigational features unwisely. Since the user population is relatively diverse, such traditional static hypermedia applications suffer from an inability to satisfy the heterogeneous needs of the many users. Moreover, with the growth of mobile and wireless communication allowed service providers to develop for users new ways of interactions through a variety of channels in an anyhow, anytime and anywhere manner, but developing also more demanding requirements. This paper makes an extensive reference to user profiling considerations. It underpins the emergence of the mobile and wireless technology and the “new” user profiling requirements that arise, with visual, emotional and cognitive processing parameters incorporated. Eventually, it proposes an adaptive Web-based educational environment based on the user perceptual preference characteristics identified.