This chapter explores the role of learning and technology, focusing on specific historical developments that revolutionized communication and expanded knowledge-building capacities, from the time of pre-linguistic and prehistoric ancestors until the present Knowledge Age. It describes the fascinating story of how learning and technology have been integral to human development from the earliest human ancestry. The four major paradigmatic shifts associated with speech, writing, printing and the internet illuminate how technology and learning formed the basis for civilizational advances. The original social software of email and group forums remain major activities on the internet, but it is the invention and adoption of social networks that marks the keystone for Web 2.0. The internet has also introduced remarkable opportunities for transforming teaching and learning and advancing online learning. In adjunct mode, the use of the internet is an add-on that complements the existing curriculum.