The nature of technology has changed since Artificial Intelligence in Education (AIED) was conceptualized as a research community and Interactive Learning Environments were initially developed. Technology is smaller, more mobile, networked, pervasive and often ubiquitous as well as being provided by the standard desktop PC. This creates the potential for technology supported learning wherever and whenever learners need and want it. However, in order to take advantage of this potential for greater flexibility we need to understand and model learners and the contexts with which they interact in a manner that enables us to design, deploy and evaluate technology to most effectively support learning across multiple locations, subjects and times. The AIED community has much to contribute to this endeavor.