The transition from conventional to more regenerative cropping systems can be economically risky due to variable transition period yields and unforeseen costs. We compared yields and economic returns for the first three years of the transition from a Business as usual (BAU) conventional corn (Zea mays)-soybean (Glycine max) rotation to an aspirational (ASP) five-crop (corn-soybean-winter wheat (Triticum aestivum)-winter canola (Brassica napus)-forage) rotation in the upper US Midwest. Regenerative ASP cropping practices included more diverse crop rotation, continuous no till, cover crops, precision inputs, and livestock (compost) integration. For the first two transition years, BAU corn yields were 8-12 % higher than ASP while in the third, 5 % lower. Soybean yields were similar for the first two years but higher in BAU in the third due to an ASP pest outbreak. Equivalent yields for other ASP crops were lower than BAU in the first two years but similar in the third, except for canola, which suffered from slug damage. Whole-system economic returns narrowed across years; by year three, whole system comparisons for the ASP corn and soybean entry points (corn-soybean-wheat and soybean-wheat-canola, respectively) showed equivalent economic returns for BAU and ASP, despite yield differences, owing largely to the ASP system’s reduced operational costs. Overall findings suggest that early regenerative systems can be as profitable as conventional with careful attention to rotation entry points and inputs.