The current generation of new students, referred to as the Millennial Generation, brings a new set of challenges to the community college. The influx of these technologically sophisticated students, who interact through the social phenomenon of Web 2.0 technology, bring expectations that may reshape institutions of higher learning. This chapter provides an overview of Web 2.0 technologies and considerations of their potential to transform the way education is delivered. Long-held learning beliefs and established educational strategies may need to be redefined to incorporate the benefits of Web 2.0 and to serve the educational needs of the Millennial Generation. (Contains 1 table.)