This article contributes to research on contextual influences on technology integration in urban mathematics classrooms through an investigation of five middle-grade teachers' participation in a laptop program. Drawing on activity theory, findings illuminate teachers' dilemmas and coping strategies in their efforts to integrate technology. Dilemmas of practice included (a) determining the role of technology, (b) meeting misaligned expectations, and (c) gaining knowledge and skills despite limited professional development. Coping strategies included (a) integrating multiple institutional goals, (b) breaking rules, and (c) redistributing instructional responsibilities across colleagues and students. Implications for administrative practice, teacher education, and future research are discussed. (Contains 2 figures and 1 note.)