In this evidence-based practice article the authors investigate the challenges that leaders (administrators, staff, and teachers) face in high schools where personnel navigate technology reform. We studied an American comprehensive high school within a large school district in southeastern United States. School administrators and teachers faced three technology-related challenges: troublesome support structures, conflicting instructor roles, and a pervasive youth digital media culture. In response, school administrators and teachers used "workarounds" that alleviated technology problems and they adopted innovative, technology-infused instructional practices. We conclude the article by providing five recommendations for district and school-based administrators: plan early for long-term support, determine teacher needs, formalize informal support networks, showcase successful instructional adaptations, and adopt student personal media device (PMD) appropriate-use guidelines.