If we concede that generational traits are in fact useful as a tool for understanding young adolescents in formal education settings today and well into the future, then we can begin to consider the effectiveness of the way we go about educating young people. To meet the needs of this generation we have to examine the systems and structures that support this education, and the teaching practices—specifically what we teach, how we teach it, and how we assess it. This is a huge challenge. Prensky (2005/6, p. 8) captures the conundrum well when he asserts that ‘schools are stuck in the 20th century. Students have rushed into the 21st. How can schools catch up and provide students with relevant education?’ This chapter sets out to tackle these issues, being structured around generally accepted generational traits and providing non-representational voice to the young people themselves through the inclusion of their own quotes and comments, serving as a sounding-board for the various propositions presented. MilGen voices will also use pseudonym cyber names, not their real names.