This article stresses that school administrators need to understand the history of education technology in order to introduce new ideas and learning opportunities to students. Pownell and Bailey (2002) described four predominant waves in the history of education technology: In the 1960s, the first phase included mainframe computers, which allowed for high-speed computation used mostly for administrative tasks. Phase two took place during the 1970s when personal computers allowed administration, teachers and students to have computer access. Phase three allowed the Internet to provide a different level of communication between school personnel during the 1990s. And the fourth phase of education technology is still evolving. The cornerstone of this fourth wave is wireless technology, which is small and mobile. This article frames some of the insights garnered from informal conversations between principals and technology specialists about what it means to integrate the latest toys from the digital world into schools.