Over the past century, numerous key technologies (including digital technologies) have been introduced into education. For the most part, each of them has been expected to revolutionise teaching and learning. However, it is generally accepted that neither dramatic reorientations nor changes in education have happened. Yet, while use of technology over the last 100 years has not resulted in a revolution, several key improvements and advancements in educational access and equity have resulted. The critical focus of this chapter is to look beyond the hype of technology and media over the last century and, instead, critically consider the significance of the changes over time in terms of how we understand teaching and learning with technology today. To explore this issue, the chapter examines what we have labelled as three 'ages' of technology integration: pre-digital, personal computer and the internet. While these three ages are described, it would be a mistake to assume that this is the only interpretation of a history of technologies in education. Depending on your geographic location, socioeconomic situation, cultural background, literacy and other variables, the history you and your family and community experience is different. For example, internet connectivity and the ensuing changes to education opportunities was available in metropolitan areas years prior to rural communities, and even today is problematic in remote areas. This chapter presents one interpretation by looking at three significant changes in technology provision in education. The technologies of each age were not adopted in education as expected, but they presented a range of benefits. These expectations and benefits will be discussed in relation to some key influencing social trends and beliefs about learning of the time. The chapter concludes by considering how a critical view of digital technologies over time informs our understanding of teaching and learning.