The 2021 fire season in Greece was the worst of the past 13 years, resulting in more than 130,000 ha of burnt area, with about 70% consumed by five wildfires that ignited and spread in early August. Common to these wildfires was the occurrence of violent pyroconvection. This work presents a meteorological analysis of this outbreak of extreme pyroconvective wildfires. Our analysis shows that dry and warm antecedent weather preconditioned fuels in the fire-affected areas, creating a fire environment that alone could effectively support intense wildfire activity. Analysis of surface conditions revealed that the ignition and the most active spread of all wildfires coincided with the most adverse fire weather since the beginning of the fire season. Further, the atmospheric environment was conducive to violent pyroconvection, as atmospheric instability gradually increased amid the breakdown of an upper-air ridge ahead of an approaching long-wave trough. In summary, we highlight that the severity and extent of the 2021 Greek wildfires were not surprising considering the fire weather potential for the period when they ignited. Continuous monitoring of the large- and local-scale conditions that promote extreme fire behavior is imperative for improving Greece’s capacity for managing extreme wildfires.