Wildland firefighters continue to die in the line of duty. Flammable landscapes intersect with bold but good-intentioned doers and trigger entrapment—a situation where personnel is unexpectedly caught in fire behaviour-related, life-threatening positions where planned escape routes or safety zones are absent, inadequate, or compromised. We often document, share and discuss these stories, but many are missed, especially when the situation is a near miss. Entrapment continues to be a significant cause of wildland firefighter deaths. Why do we still not know how to prevent them? We review a selection of entrapment reports courtesy of the Wildland Fire Lessons Learned Centre (WFLLC) and focus on human factors involved in entrapment rather than the specifics of fire behaviour and the environment. We found that in order for operational supervisors to make more informed strategic and tactical decisions, a more holistic and complete trend analysis is necessary of the existing database of entrapment incidents. Analysis of the entrapment data would allow training to include a more fulsome understanding of when suppression resources are applying strategies and tactics that might expose them to a higher likelihood of entrapment. Operational supervisors would make more informed decisions as to where and when to deploy resources in critical situations in order to reduce the exposure to unnecessary risk of entrapment.