Optimized wildfire risk reduction strategies are generally not resilient in the event of unanticipated, or very rare events, presenting a hazard in risk assessments which otherwise rely on actuarial, mean-based statistics to characterize risk. This hazard of actuarial approaches to wildfire risk is perhaps particularly evident for infrequent fire regimes such as those in the temperate forests west of the Cascade Range crest in Oregon and Washington, USA (“Westside”), where fire return intervals often exceed 200 years but where fires can be extremely intense and devastating. In this study, we used wildfire simulations and building location data to evaluate community wildfire exposure and identify plausible disasters that are not based on typical mean-based statistical approaches. We compared the location and magnitude of simulated disasters to historical disasters (1984–2020) in order to characterize plausible surprises which could inform future wildfire risk reduction planning. Results indicate that nearly half of communities are vulnerable to a future disaster, that the magnitude of plausible disasters exceeds any recent historical events, and that ignitions on private land are most likely to result in very high community exposure. Our methods, in combination with more typical actuarial characterizations, provide a way to support investment in and communication with communities exposed to low-probability, high-consequence wildfires.