Today’s portals bring together existing technologies in useful, innovative ways, but they don’t scratch the surface of what is possible. The constant build-up of information and resources on the World Wide Web demands a smarter more advanced portal technology that offers dynamic, personalized, customized, and intelligent services. This chapter discusses next-generation portals and the requirement that they come to know their users and understand their individual interests and preferences. It describes a new generation of portals that have a level of autonomy, making informed, logical decisions and performing useful tasks on behalf of their members. The chapter highlights the role of artificial intelligence in framing the next generation of portal technology and in developing their capabilities for learning about their users.