Extreme wildfires are increasingly rising to intense and uncontrolled fires, with dimension and destructive potentials that are greater than what has been seen and dealt with. The hazards posed by these fires increase significantly when they approach the wild–urban interface, with relevant environmental and socio-economic consequences. The 2009 Victorian bushfires and the 2017 Portugal wildfires are powerful reminders, and they have demonstrated the need to better understand why mitigation plans have failed to protect the community in these events and to improve community resilience. The year 2017 is a milestone in the history of wildfires in Portugal, not only because of the vast burned area but also due to the high number of fatalities. The two occurrences were at different times (June and October) but were geographically close (region of centre of Portugal). A total of 117 deaths occurred in both events and 92% of the victims were in wild–urban interface areas. This paper analyses and discusses the characteristics and causes of death of the victims of these two events: age, place of death, distance from place of death to place of residence and last-minute choices to aim to understand the actions that people took in the face of the approaching fire, which led to their death. In both cases, most people died fleeing the fire without any information from the competent authorities. In the end, it is possible to identify risk factors that lead to the death of civilians due to wildfires, such as the increase in demand for rurality by young people from big cities with no previous contact with wildfires; on the other hand, there is the ageing of the population residing in forest areas, who were previously physically and structurally prepared to deal with fires and are currently no longer able to.