Abstract Crop producers transitioning from conventional to organic management must grow crops with organic practices but no price premium during the transition, while incurring higher production costs and lower yields. We evaluated red clover-maize, maize-soybean, and soybean-wheat/red clover rotations in organic and conventional cropping systems with recommended and high inputs to identify the best rotation and management practices during the transition. Organic maize with recommended inputs compared with conventional maize with high inputs in the red clover-maize rotation had similar yields, lower production costs, and higher partial returns. Organic compared with conventional maize in the maize-soybean rotation had lower yields, higher production costs, and lower partial returns. Organic compared with conventional soybean with recommended inputs in soybean-wheat/red clover or maize-soybean rotations had similar yields, production costs, and partial returns. Organic compared with conventional wheat with recommended inputs had lower yields, higher production costs, and lower partial returns. The organic compared with the conventional soybean-wheat/red clover rotation had the least negative impact on partial returns. All organic rotations with recommended inputs had mostly similar partial returns so transitioning immediately, regardless of entry crop, appears most prudent. High input management, which did not improve organic crop yields, would not ease the transition. Acknowledgement :