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Biochar may improve soil hydrology by altering soil porosity, density, hydraulic conductivity, and water-holding capacity. These properties are associated with the grain size distributions of both soil and biochar, and therefore may change as biochar weathers. Here we report how freeze-thaw (F-T) cycling impacts the grain size of pine, mesquite, miscanthus, and sewage waste biochars under two drainage conditions: undrained (all biochars) and a gravity-drained experiment (mesquite biochar only). In the undrained experiment plant biochars showed a decrease in median grain size and a change in grain-size distribution consistent with the flaking off of thin layers from the biochar surface. Biochar grain size distribution changed from unimodal to bimodal, with lower peaks and wider distributions. For plant biochars the median grain size decreased by up to 45.8% and the grain aspect ratio increased by up to 22.4% after 20 F-T cycles. F-T cycling did not change the grain size or aspect ratio of sewage waste biochar. We also observed changes in the skeletal density of biochars (maximum increase of 1.3%), envelope density (maximum decrease of 12.2%), and intraporosity (porosity inside particles, maximum increase of 3.2%). In the drained experiment, mesquite biochar exhibited a decrease of median grain size (up to 4.2%) and no change of aspect ratio after 10 F-T cycles. We also document a positive relationship between grain size decrease and initial water content, suggesting that, biochar properties that increase water content, like high intraporosity and pore connectivity large intrapores, and hydrophilicity, combined with undrained conditions and frequent F-T cycles may increase biochar breakdown. The observed changes in biochar particle size and shape can be expected to alter hydrologic properties, and thus may impact both plant growth and the hydrologic cycle.