This article investigates how participants in simulations of extreme events handle inadequacy, contributing to the discussion on workplace learning in high-pressure and unpredictable scenarios. The study is based on ethnographic fieldwork conducted across five simulations in three organizations (military, police, and county administrative board), involving 288 h of observations, ethnographic interviews, and 18 semi-structured interviews. The analysis focused on identifying episodes where participants encountered inadequacy, exploring how they recognized, attributed, and addressed it. Our findings reveal that inadequacy disrupts routine practices but also fosters opportunities for learning and innovation. Key conditions for effectively handling inadequacy include the voicing of inadequacy, which requires psychologically safe environments, and proactive responses such as improvisation or acceptance under urgency. Additionally, simulations, while controlled and artificial, effectively expose inadequacies, revealing gaps in preparedness that can inform future crisis responses. This article contributes to professional learning by highlighting inadequacy as a critical factor in both individual and collective learning, offering insights into how simulations can be designed to enhance preparedness for unpredictable, high-stakes events.