Digitalization is transforming the audit profession. Apprenticeship norms prescribe that knowledge flows down from supervisors to subordinates, but digitalization increasingly positions junior auditors as experts in emerging technology. Consequently, supervisors can learn from subordinates. This reversal challenges long-standing apprenticeship expectations, yet little is known about how it unfolds or the tensions it creates. Against this backdrop, we examine tensions that can arise when subordinate auditors share their knowledge with supervisors. Drawing on 51 semistructured interviews and guided by theory, we identify four recurring roadblocks to upward knowledge sharing: junior auditors' status motives, “same as last year” routines, status insecurity among immediate supervisors, and defensiveness when juniors cross perceived knowledge “lanes.” We also find a rare, countervailing pathway: the emergence of informal champions who legitimize junior auditors' contributions. Our study deepens understanding of how digitalization transforms team learning in audits and shows how historical structures and norms evolve under new conditions. Data Availability: Data were obtained from interviews.