This chapter examines why UNHCR struggles to transform training into genuine learning. While individual motivation is high, systemic barriers—such as hierarchy, silos, and a fear of mistakes—stifle reflection and adaptation. Drawing on Argyris and Schön, the analysis demonstrates how the UNHCR operates within a single-loop learning culture, correcting errors without questioning the underlying frameworks. Evaluations confirm that workshops and technical trainings provide reassurance but rarely alter ingrained practices. Psychodynamic theory suggests that such ritualised learning functions as a defence against institutional anxiety about failure and relevance. Personality data reinforce the picture: leaders often display risk aversion, overcontrol, or resistance to feedback, which can create blind spots and hinder innovation. Gallup surveys reveal that few staff members feel supported in their growth and professional development. The result is a culture where knowledge flows downward but rarely circulates horizontally, slowing adaptation in fast-moving crises. Without embedding curiosity, dialogue, and psychological safety, UNHCR risks outdated responses and diminished refugee protection.