<p>Mistakes at work are inevitable and can either foster learning and development or severely harm one’s professional career. Because career outcomes often depend on how mistakes are evaluated by involved individuals (e.g. supervisors), understanding the factors that shape such evaluations is crucial for organizations seeking to promote learning while avoiding unfair career penalties. Drawing on Expectation–Confirmation Theory (ECT), the present study investigates two different types of mistakes at work: mistakes in routine and complex work tasks. In two experiments with 192 alumni of a German university I tested whether mistakes in routine tasks are judged differently than mistakes in complex work tasks. Results consistently show that mistakes occurring in routine tasks are judged significantly more negatively than mistakes in complex tasks. These findings point to a dilemma of workplace mistakes as dual-process theories suggest that mistakes are more likely to occur in routinized tasks due to automatic processing, yet these very mistakes are evaluated more harshly. This mismatch may create systematic disadvantages for employees primarily performing routinized work. I discuss practical implications and propose an intervention aimed at reducing mistakes in routine tasks. My findings highlight the importance of task characteristics in shaping social judgments of workplace mistakes and underscore the need for organizational practices that both acknowledge expectation dynamics and proactively prevent errors in routine performance contexts.</p>