Teacher education graduates in their early years of service are ill-prepared to act as building-level change agents who can advocate for the enhanced use of technology in the classroom. In this study, a group of experienced teachers seeking the M.Ed. in Educational Technology suggest that the lack of confidence which new teachers show in relation to technology can be traced back to the absence of rigorous technical skill-building in both their Introduction to Educational Technology class and methods classes. These tech-savvy mid-career teachers then identify obstacles to enhancing pre-service teacher education programs with more effective preparation in teaching with technology and discuss ways to overcome these obstacles. They conclude that a rethinking of how technology teacher training programs are conceptualized and administered is needed.