In this technology-oriented age, teachers face daily decisions regarding the use of advanced digital technologies—graphing calculators, dynamic geometry software, blogs, wikis, podcasts and the like—to enhance student mathematical understanding in their classrooms. In this case study, the authors use the Technological, Pedagogical, and Content Knowledge (TPACK) model in conjunction with a five-stage developmental model, which can be used to describe growth in TPACK to describe the initial attempts of a teacher, Jane, to develop TPACK as she learns and attempts to integrate an advanced teaching technology into her classroom, namely the TI-Nspire graphing calculator. The study tracks her struggles to reconcile some traditional beliefs about how students learn with her desire to be responsive to what she perceives as affordances of advanced digital technologies. Main data collection methods were journal writing, observations, document analysis, and interviews. Using the five-stage developmental model, we saw that this experience helped Jane to move among different stages. This study showed that the TPACK model with the five-stage developmental model can be a beneficial tool for researchers to study teachers' professional growth and is also a valuable tool for teachers to reflect on their own growth.