Teaching is a complex profession, which is further complicated by the integration of technology into classrooms. Reflection can help teachers unpack the complexity in their practice. Reflection can be an effective instructional strategy in helping preservice teachers develop technological pedagogical content knowledge (TPACK), the complex and dynamic knowledge necessary for effective technology integration into instruction. In this study, reflective activities were integrated into a Learning By Design (LBD) environment, which was created to help preservice teachers develop TPACK. This paper investigated the participants’ TPACK development and examined how reflection helped them construct TPACK. Through content analysis of the participants’ reflective journals, the researcher found that the preservice teachers developed initial TPACK awareness. However, their reflection in technology knowledge and the content aspects of TPACK were limited and superficial. Interviews with the participants showed reflection helped the preservice teachers remember what they learned by describing and elaborating on their in-class experiences, pushed them to think about how to apply what they learned in their future classrooms, and helped them become more reflective and open-minded about using technology in classrooms. Finally, the researcher discussed this study’s implications for teacher educators and researchers.