This article describes the transformations that took place as two veteran teachers grappled with the insertion of video-mediated videoconferencing (VMC) for practicums during an initial study that focused on teacher candidates. Through their stories, the following themes were identified: teacher as risk-taker, VMC as a motivating device to promote student participation in learning, reassessment of teaching practices, and teacher change. Findings indicate that (a) cooperating teachers need to strive for realism and not for perfection during demonstrations, (b) school-university partnerships can be fostered through 21st-century technologies, and (c) informed and supportive stakeholders within the school community can impact participation and learning from newly implemented VMC supervision techniques. Lessons learned can be helpful for teacher educators, K-12 administrators and teachers, and technology support personnel who desire to assist teachers in embedding supportive technologies for teacher education.