This article describes the critical experiences of a middle school mathematics teacher as she progressed from a novice to a knowledgeable creator of technology-enhanced learning activities for her classroom. During an eight week intervention, cognitive apprenticeship strategies (Collins, 1991) were utilized in a partnership with the teacher until she felt empowered to independently create these activities without further coaching or support. Qualitative research methods were used to determine the primary factors that lead to such empowerment, as well as the instructional and learning values that the teacher promoted in the activities. This research effort demonstrated that autonomy, confidence, and awareness were prevalent characteristics shown with successful design, development, and implementation of technology-enhanced learning activities. In addition, the teacher's creation of activities was influenced by the teacher's learning values associated with challenging inquiry and continual improvement. Implications from this research effort examine the conditions and support needed to diffuse learned strategies among a community of teachers for broader development and implementation of technology-enhanced learning activities.