As digital technologies become increasingly central to classroom instruction, teachers are expected not only to possess digital competence but also to translate that competence into effective instructional practice. However, growing evidence suggests a persistent gap between teachers’ digital self-efficacy and their actual classroom use of digital tools. This study examines how teachers’ professional backgrounds shape this confidence–practice relationship by focusing on two key contextual factors: qualification pathway and first-career status. Using data from 1,094 U.S. teachers nested within 149 schools from the TALIS 2024 dataset, we employed multilevel modeling to investigate how digital self-efficacy and digital attitudes predict classroom digital tool use and how these associations differ across teacher subgroups. Results indicate that both digital self-efficacy and digital attitudes are strong, positive predictors of classroom digital use. While the qualification pathway and first-career status show limited direct effects, they play an important moderating role. Teachers who entered through traditional qualification pathways and had prior professional experience demonstrated the strongest alignment between digital confidence and classroom practice. In contrast, first-career teachers—particularly those entering through alternative routes—exhibited a weaker translation of digital self-efficacy into instructional use, revealing a pronounced confidence–practice gap. These findings suggest that teachers’ ability to enact digital competence depends not only on individual beliefs but also on their preparation and career backgrounds. Implications highlight the need for differentiated induction and professional development supports, especially for first-career teachers in alternative pathways, to help bridge the gap between perceived competence and classroom implementation of digital tools.