In this article, the authors present a technology-based innovation called eSupervision, a student teaching supervision program created to improve the field experience by using cognitive apprenticeship as a framework for its design. The authors analyze program implementation to determine whether eSupervision functions as it was designed. The results of this study indicate that building a technology-enhanced supervision experience around the framework of cognitive apprenticeship is a viable and productive approach to re-imagining the field experience of student teachers.