The National Weather Service (NWS) considers frequent gusty downslope winds, accompanied by rapid warming and decreased relative humidity, among the most significant weather events affecting southern California coastal areas in the vicinity of Santa Barbara (SB). These extreme conditions, commonly known as "sundowners", have affected the evolution of all major wildfires that impacted SB in recent years. Sundowners greatly increase fire, aviation and maritime navigation hazards and are thus a priority for regional forecasting. Currently, the NWS employs the Weather Research Forecasting (WRF) model at 2 km resolution to complement forecasts at regional-to-local scales. However, no systematic study has been performed to evaluate the skill of WRF in simulating sundowners. This research presents a case study of an 11-day period in spring 2004 during which sundowner events were observed on multiple nights. We perform sensitivity experiments for WRF using available observations for validation and demonstrate that WRF is skillful in representing the general mesoscale structure of these events, though important shortcomings exist. Furthermore, we discuss the generation and evolution of sundowners during the case study using the best performing configuration, and compare these results to hindcasts for two major SB fires. Unique, but similar, profiles of wind and stability are observed over SB between case studies despite considerable differences in large-scale circulation, indicating that common conditions may exist across all events. These findings aid in understanding the evolution of sundowner events and are potentially valuable for event prediction.