<p>This article explores how three upper secondary teachers engaged with pedagogical uncertainty during a year of classroom interventions in a postdigital context. Uncertainty was conceptualised as an open situation requiring deliberate pedagogical choice. The study examines how teachers articulated and responded to uncertainty, and how their understanding evolved over time. Findings highlight the generative role of uncertainty in deepening student understanding, strengthening teacher–student relationships, and supporting teacher professional development. Situated within the entangled realities of postdigital education, the study offers a conceptual contribution to understanding pedagogical uncertainty as a relational and productive element of contemporary teaching practice.</p>