The purpose of this study is to document the perceptions of school leaders pertaining to the benefits and challenges of technology in high schools located on Prince Edward Island (PEI) (Canada). For this qualitative study, we interviewed 11 educational leaders representing the PEI Department of Education, principals, vice-principals, and department heads. Most participants indicated that technology activated reverse mentorship among teachers and students, and technology positively affected student motivation. In contrast, the participants recognized there were challenges regarding the impact of technology at the high school level. The challenges identified were inappropriate texting, decline of literacy skills, policy and lack of policy, and increased workload regarding communication with parents. Herein, we apply Freirean perspectives, which promotes social advocacy, to understand how these benefits and challenges interrelate.