Sundowner winds are downslope gusty winds often observed on the southern slopes of the Santa Ynez Mountains (SYM) in coastal Santa Barbara (SB), California. They typically peak near sunset and exhibit characteristics of downslope windstorms through the evening. They are SB’s most critical fire weather in all seasons and represent a major hazard for aviation. The Sundowner Winds Experiment Pilot Study was designed to evaluate vertical profiles of winds, temperature, humidity, and stability leeward of the SYM during a Sundowner event. This was accomplished by launching 3-hourly radiosondes during a significant Sundowner event on 28–29 April 2018. This study showed that winds in the lee of the SYM exhibit complex spatial and temporal patterns. Vertical profiles showed a transition from humid onshore winds from morning to midafternoon to very pronounced offshore winds during the evening after sunset. These winds accompanied mountain waves and a northerly nocturnal lee jet with variable temporal behavior. Around sunset, the jet was characterized by strong wind speeds enhanced by mountain-wave breaking. Winds weakened considerably at 2300 PDT 29 April but enhanced dramatically at 0200 PDT 29 April at much lower elevations. These transitions were accompanied by changes in stability profiles and in the Richardson number. A simulation with the Weather Research and Forecasting (WRF) Model at 1-km grid spacing was examined to evaluate the skill of the model in capturing the observed winds and stability profiles and to assess mesoscale processes associated with this event. These results advanced understanding on Sundowner’s spatiotemporal characteristics and driving mechanisms.