Fall cover crops are grown to protect soil from erosion from the time of cash crop harvest to the following cash crop and to benefit soil health. The adoption of fall cover crops in Manitoba has increased in recent years due to increasing interest in soil health building practices. Major barriers to cover crop adoption in Manitoba include the limited amount of previous research and the short growing season which limits the fall window for cover crop growth, and thus may limit the potential benefits of cover crops. This study assessed fall cover crops in the initial years of adoption in six multiyear on-farm experiments across Manitoba with four replicates in each environment. Fall cover crops were included in the annual cash crop rotation and were compared to the natural fall plant community (NFPC) from 2019 until 2021. This research assessed the fall dry matter production of fall cover crops, the effect on subsequent cash crop yield, along with effects on soil nitrate, moisture, and health. Additionally, the short-term economic cost benefit analysis of fall cover crops was explored. Cover crops were included after 13 of the 17 cash crops with seeding dates ranging from August 10th to September 14th. The mean fall cover crop dry matter ranged from 99 to 2146 kg ha-1. The cover crop and NFPC produced equivalent amounts of fall dry matter in 7 of 11 environments. Fall cover crops significantly decreased the overall subsequent mean cash crop yield by 2% compared to the NFPC. Spring soil nitrate was significantly lower in the cover crop treatment in 3 of 5 environments relative to the NFPC treatment. After 2 or 3 cover crops were grown in each environment, the mean Saskatchewan Soil Health Assessment score was significantly greater in the cover crop treatment. Fall cover crops resulted in a mean economic loss of $163 ha-1. The high mean economic loss observed in this study suggests incentive payments will be necessary for fall cover crops to be economically feasible in Manitoba.