A new generation of web-based tools, referred to as Web 2.0, allows users to organize information, to create and edit content, and to collaborate with others. The skills developed and practiced through the use of these tools are the same skills valued by 21st century employers. Web 2.0 tools offer schools the potential to engage students in assignments demonstrating authentic uses of technology. While students have embraced these tools in their personal lives, school districts remain hesitant to adopt Web 2.0 applications due to safety concerns. This chapter explores potential and actual uses of Web 2.0 in schools, the changes occurring in the business world as a result of these new technologies, and the implications for today's students and educational systems. [For the complete volume, "Educational Media and Technology Yearbook, Volume 34," see ED602586.]