More and more digital technologies are being integrated into school learning, and one strategy by policymakers to reinforce this trend is employing digital one-to-one approaches. For digital technologies to be fruitfully integrated into school-based learning scenarios, teachers and their anticipations are key. In our study, we want to explore how internal, external and technological factors affect the instructional anticipations of mathematics teachers in a digital one-to-one educational environment. Therefore, we employed a modified model of the Unified Theory of Acceptance and Use of Technology. Through our structural equation study, in which data from more than 900 mathematics teachers were analyzed, we identified that especially technological and external factors can predict mathematics teachers’ instructional anticipations. Findings from our study could be particularly relevant for educational policymakers, informing them about the importance of factors or interventions related to educational technology implementation.