The radiometric uncertainty of Synthetic Aperture Radar (SAR) observations and weather-related surface conditions caused by frozen conditions, snow and intercepted rain affect the backscatter ( σ0 ) observations and limit the accuracy of soil moisture retrievals. This study estimates Sentinel-1’s radiometric uncertainty, identifies the effects of weather-related surface conditions on σ0 and investigates their impact on soil moisture retrievals for various conditions regarding soil moisture, surface roughness and incidence angle. Masking rules for the surface conditions that disturb σ0 were developed based on meteorological measurements and timeseries of Sentinel-1 observations collected over five forests, five meadows and five cultivated fields in the eastern part of the Netherlands. The Sentinel-1 σ0 observations appear to be affected by frozen conditions below an air temperature of 1 ∘C , snow during Sentinel-1’s morning overpasses on meadows and cultivated fields and interception after more than 1.8 m m of rain in the 12 h preceding a Sentinel-1 overpass, whereas dew was not found to be of influence. After the application of these masking rules, the radiometric uncertainty was estimated by the standard deviation of the seasonal anomalies timeseries of the Sentinel-1 forest σ0 observations. By spatially averaging the σ0 observations, the Sentinel-1 radiometric uncertainty improves from 0.85 dB for a surface area of 0.25 ha to 0.30 dB for 10 ha for the VV polarization and from 0.89 dB to 0.36 dB for the VH polarization, following approximately an inverse square root dependency on the surface area over which the σ0 observations are averaged. Deviations in σ0 were combined with the σ0 sensitivity to soil moisture as simulated with the Integral Equation Method (IEM) surface scattering model, which demonstrated that both the disturbing effects by the weather-related surface conditions (if not masked) and radiometric uncertainty have a significant impact on the soil moisture retrievals from Sentinel-1. The soil moisture retrieval uncertainty due to radiometric uncertainty ranges from 0.01 m3 m−3 up to 0.17 m3 m−3 for wet soils and small surface areas. The impacts on soil moisture retrievals are found to be weakly dependent on the surface roughness and the incidence angle, and strongly dependent on the surface area (or the σ0 disturbance caused by a weather-related surface condition for a specific land cover type) and the soil moisture itself.