Changes in the hydrologic regime impose great challenges for grain production. We investigated the impact of dry and wet extremes on the recent losses of crops in Severo-Kazakhstanskaya Oblast (SKO), where 25% of Kazakhstan’s wheat is produced. We reconstructed the Palmer Drought Severity Index (June–August PDSI) and average grain yields (with an explained variance of 48% and 44%, respectively) using five tree ring width chronologies. The extended history of the moisture variability and yields of spring wheat, oats, and barley shows the strong impact of hydrology, rather than the heat, on the grain production. We defined three distinctive hydrologic regimes in SKO: (1) 1886–1942, (2) 1943–1977, (3) 1978–2023. The early regime had fewer drought events, including some that covered a single year. Their duration increased up to 3 years in the second period. The latest regime is an extreme mode of hydrologic variability with events abruptly switching from extremely dry to extremely wet conditions (called “whiplash”). The 21st century regime signifies that the intensified and prolonged decade-long drought transitioned into pluvial condition. The new regime created sizable instability for grain producers. This crop yield reconstruction denotes the potential of the tree-ring proxy for understanding the impact of climate change on the agriculture and food security of Central Asia.