Damaging gusts in windstorms are represented by crude subgrid-scale parameterizations in today’s weather and climate models. This limitation motivated the Wind And STorms EXperiment (WASTEX) in winter 2016-17 in the Upper Rhine Valley over southwestern Germany. Gusts recorded at an instumented tower during the passage of extratropical cyclone "Thomas" on 23 February 2017 are investigated based on measurements of radial wind with ≈70-m along-beam spacing from a fast-scanning Doppler lidar and realistic large-eddy simulations with grid spacings down to 78 m using the ICOsahedral Nonhydrostatic model. Four wind peaks occur due to the storm onset, the cold front, a precipitation line, and isolated showers. The first peak is related to a sudden drop in dew point an results from the downward mixing of a low-level jet and a dry layer within the warm sector characterized by extremely high temperatures for the season. While operational convection-permitting forecasts poorly predict the storm onset overall, a successful ensemble member highlights the role of upstream orography. Lidar observations reveal the presence of long-lasting wind structures that result from a combination of convection- and shear-driven instability. Large-eddy simulations contain structures elongated in the wind direction that are qualitatively similar but too coarse compared to the observed ones. Their size is found to exceed the effective model resolution by one order of magnitude due to their elongation. These results emphasize the need for sub-km scale measuring and modeling systems to improve the representation of gusts in windstorms.