Land rolling has become a popular practice in soybean and pulse production in the Northern Great Plains. The practice of land rolling is simply pulling a large-scale cylindrical roller over a cultivated field to push down stones and improve seed-to-soil contact. Many soybean farms in Manitoba are routinely rolled either immediately after seeding or at the very early stages of crop development. There has been considerable concern regarding the potential effects of land rolling on wind-induced soil loss, soil properties, and plant growth in soybean production. To address this concern, an on-farm research project was conducted at eight different field sites in the Red River Valley of southern Manitoba, Canada, in 2018 and 2019. Trials were established with rolled and non-rolled treatments arranged using a randomized complete block design. To examine the environmental and agronomic impacts of land rolling, data was collected to characterize wind-transported sediment (passive uni-directional samplers), soil properties (e.g., surface roughness and moisture content), yield, and plant growth parameters. Despite the land rolling reducing surface roughness the results showed no significant difference in the amount of collected wind-transported sediment between the two treatments. In addition, the particle size of the wind-transported sediment ranged between 0.002 and 0.1 mm suggesting that this size fraction is the most susceptible to wind erosion. Furthermore, there was a small, but significant, increase in soybean yield in the non-rolled treatment, despite having significantly lower volumetric soil moisture content. Overall, while land rolling reduced soil surface roughness and increased the wind erosion risk, it did not result in an increase in the amount of wind-transported soil loss. Lastly, within the Red River Valley the practice of land rolling to support higher soybean yield was not supported; however, the exact reasons for the small yield reduction is not fully understood.