Despite the transformative power that technology has had in a whole range of businesses, the history of technology use in education over the last 100 years paints a rather bleak picture of the extent to which digital tools, in and of themselves, can lead to sustainable academic change. The issue is that we often miss the key affordances of the tools that can be employed to help solve learning problems. This presentation traces the lessons we can learn from the history of educational technology in order to explore the true promise of openly licensed educational resources and the future they may hold for teaching, learning, and student success.