This research was conducted during the 2009-2010 school term as a case study of a large school division’s technology initiative after eight years to chronicle its effect on high school business and marketing teachers’ use and integration of technology. The 18 teachers were business and marketing teachers from eight high schools, two technical centers and one alternative school who participated in the one-to-one laptop initiative from its inception and who were asked to participate in the study. A web-based survey on technology use and adoption was administered to 18 high school business and marketing teachers. The researcher conducted a total of four unannounced observations of each teacher’s instruction, specifically for technology use, by using the Instructional Technology Resource Teachers’ Technology Integration form. Additionally, the teachers were asked to participate in one of two focus group interviews to determine their level of technology use along with their perceptions regarding the technology initiative and its effect on their instruction and teaching strategies. This case study has relevance to school districts with technology initiatives or districts considering adopting one. The high school business and marketing teachers’ vantage point provided unique information about the effect a one-to-one laptop initiative has made on business and marketing teachers’ technology use over the last eight years. The effect that a comprehensive, one-to-one initiative had on business and marketing high school teachers’ technology use was twofold. First, instruction was affected. Teachers and students were found to manage data electronically, the amount of and methods for teachers’ communication changed, and exemplars surfaced. Second, challenges emerged. Teachers’ classroom management responsibilities included laptop monitoring, access issues as a consequence of network filtering policies, and a need for additional technology-based professional development for teachers and time to practice new skills. While some positive effects were visible, eight years into the one-to-one laptop initiative problems were evident, and administrative support as well as teacher acceptance seemed to play an important role in teachers’ willingness to regularly and enthusiastically modify their pedagogy to include technology in teaching strategies and student lessons