Behind CALL teacher education (CTE) there is an unproblematized consensus of transfer, which suggests a positivist and tool-centered view of learning gains that differs from the sociocultural focus of recent teacher education research. Drawing on Beach’s (2003) conceptualization of transfer as consequential transition, this qualitative study seeks a cross-contextual understanding of language teacher learning with digital technology as the teachers in this study moved from a CTE course back to their own teaching contexts. Near the end of a CTE course, 19 in-service language teachers were asked to build connections between their experiences in the course and their teaching by creating a presentation. Four types of connections were identified, including thoughtful action planning, past experience refinement, and limited and reluctant use. In-depth interviews eight months later with four of the teachers found that they could seldom use the tools in the ways they had planned. However, they each experienced consequential transition as they struggled to reflect on their CTE course experience in everyday teaching. These results challenge the view that transfer in CTE must be about using technology. It is suggested that a focus on critical reflection of technology use may encourage teachers to continue reflective engagement in the ever-changing and complicated digital learning and teaching context.