The purpose of this article is to describe lessons learned from studying the leadership in eight award-winning secondary schools and districts that were recognized for successfully leveraging technology as part of their efforts for school improvement. Data were collected through observations, interviews, and document analysis in schools and districts with ethnically, linguistically, and socioeconomically diverse students in communities facing the types of challenges that many schools face today. Based on the cross-case analysis of eight intrinsic case studies, this article offers numerous examples and lessons learned about the role that leadership and vision, technology planning and support, professional development, curriculum and instructional practices, school culture, funding, and partnerships play in leveraging technology for school improvement.