The nature of the Intelligent Tutoring System research has evolved during the years to become one of the major conceptual as well as practical source of innovation for the wider area of Human Learning support by advancements in Informatics. In the invited paper we present our view on the synergic support of Informatics research and the Human Learning context – in the tradition started by Alan Kay with Smalltalk and the Dynabook more that 30 years ago – down to the most concrete plans and results around Agents, the GRID and Human learning as a result of Human and Artificial Agent’s conversations. The paper will be organised around three questions: what?, why?, how?.