The purpose of the Technology and High School Success (THSS) initiative was to encourage innovative strategies focused on improving provincial high school completion rates, using technology and student-centered learning to engage student interest. The primary purpose of this paper is to report on barriers that impede systemic, effective and sustainable technology integration within schools. Even with teacher and administrative support and commitment for THSS, evaluative research indicated minimal change in system capacity as a result of the initiative. Three primary barriers to program sustainability were: (1) schools and school districts did not leverage the opportunity to revisit their existing vision(s), (2) schools and school districts did not use data to make changes, and (3) limited access to technology.