We present the longest data set of observed soil moisture available in the world, 45 yr of gravimetrically-observed plant available soil moisture for the top 1 m of soil, observed every 10 days for April–October for 141 stations from fields with either winter or spring cereals from the Ukraine for 1958–2002. We averaged the summer observations over the entire region to account for the observed scale of soil moisture variations, to enhance the portion of the variance that is related to meteorological forcing. The observations show a positive soil moisture trend for the entire period of observation, with the trend leveling off in the last two decades. Although models of global warming predict summer desiccation in a greenhouse-warmed world, there is no evidence for this in the observations yet, even though the region has been warming for the entire period. While the interannual variations of soil moisture simulated by both the European Centre for Medium-range Weather Prediction and the National Centers for Environmental Prediction/National Center for Atmospheric Research reanalyses are close to the observations, neither reanalysis simulates the observed upward trend. Climate model simulations for the period show the same general shape as the observations, but differ quite a bit from each other and from the observations. An observed downward trend in insolation may have produced a downward trend in evaporation and may have contributed to the upward soil moisture trend.