In this chapter, the authors explore perspectives on the notion of “digital natives” and present a case in which Web 2.0 technologies were introduced to students. They discuss studies critical of the generational metaphor, and argue that it should not be uncritically assumed that there is a generation of digital natives, but that young people may need to develop skills often associated with the digital natives. The authors present a case reflecting these pedagogical aims, involving an online Web 2.0 learning environment called Ekademia. The findings of the case reflect a gap between the researchers’ intentions and the actual outcomes. In particular, the learning environment failed to provide sufficient scaffolding for the students, who needed more support than was assumed. It is therefore suggested that educational use of social software technologies should have stronger connections to curricular activities, involve a more concerted pedagogical effort, and be supported by a higher degree of institutionalization.