Preservice teachers (PSTs) often feel unprepared to utilize digital tools in meaningful ways that support learning in the elementary classroom. It is imperative that teacher preparation programs provide support in this area so that children can learn to use digital tools to communicate in the 21st century. Previous research suggests that the Technology Integration Planning Cycle (TIPC) can support teachers in making wise decisions related to the use of digital tools to support a literacy goal. In the present study, the authors examined how the TIPC can be used with PSTs as they develop technological, pedagogical, and content knowledge and design literacy lessons that integrate a digital tool. Design-based research was used to frame their inquiry across three iterations and make formative decisions based on the ongoing collection and analysis of data. Results of this study demonstrate that with significant scaffolding the TIPC can support PSTs in designing meaningful literacy lessons. In addition, evidence collected over time suggests that PSTs engage with the TIPC in a recursive rather than linear manner.