There is a dearth of research on the mechanisms for preservice teachers’ development of the pedagogical knowledge necessary for effective use of such technologies. We explored the emergent Technological Pedagogical and Content Knowledge (TPACK) (Niess 2005, 2006, 2007) of a group of secondary mathematics preservice teachers in a methods course as they designed and implemented technology-rich teaching materials in field settings. Participant surveys and collected assignments were analyzed through the lens of the TPACK framework. The data were also analyzed to examine the trajectory of the participants’ beliefs about the appropriate role of advanced digital technologies in mathematics. The results indicate that the participants’ understanding of technology shifted from viewing technology as a tool for reinforcement into viewing technology as a tool for developing student understanding. Collected data supports the notion that preservice teacher TPACK development is closely related to a shift in identity from learners of mathematics to teachers of mathematics. In a class where advanced digital technologies were used extensively as a catalyst for promoting inquiry-based learning, preservice teachers retained a great deal of skepticism about the appropriateness of using technology in concept development roles, despite their confidence that they can incorporate technology into their future teaching.