Two high school mathematics teachers who use Interactive Whiteboards (IWBs) in the classroom were interviewed annually over the course of three years regarding their perceptions of the technology. During the third year, the two teachers were asked to complete the Concerns-Based Adoption Model Stages of Concern Questionnaire. The data obtained from the questionnaire and their responses to the annual interviews were then compared and contrasted with results from the Apple Classrooms of Tomorrow (ACOT) study, the ACOT Model of Instructional Evolution, and the Apple Classrooms of Tomorrow – Today (ACOT2) design principles. This study’s findings indicate that IWBs provide some of the same benefits as the multitude of computers and other technologies available in ACOT classrooms: increased student motivation, more dynamic instruction, and greater teacher collaboration. Unlike the ACOT technologies, however, IWBs did not lead to the implementation of more project-based instruction.