When teachers develop successful instructional strategies and efficient classroom management, they establish control and assert authority so that learning can take place in the classroom. The teachers’ experiences with wireless laptop technology in this study, however, demonstrate that ubiquitous access to this technology in the classroom can sometimes create challenges for teachers, from managerial, curricular, to communicative perspectives. Exploring these challenges and their complexities in this report is meant to present a more balanced picture of technology integration in education, the one that takes into account not only the affordances and the possibilities but also the challenges and the constraints of it for teacher pedagogy and student learning. The analysis concludes with implications for professional development and policy.