Climate change affects the heat and water resources required by agriculture, thus shifting cropping rotation and intensity. Shanghai is located in the Taihu Lake basin, a transition zone for various cropping systems. In the basin, moderate climate changes can cause major shifts in cropping intensity and rotation. In the present study, we integrated observational climate data, one regional climate model, land use maps, and agricultural statistics to analyze the relationship between heat resources and multi-cropping potential in Shanghai. The results of agro-climatic assessment showed that climate change over the past 50 years has significantly enhanced regional agro-climatic resources, rendering a shift from double cropping to triple cropping possible. However, a downward trend is evident in the actual multi-cropping index, caused principally by the increasing costs of farming and limitations in the supply of labor. We argue that improving the utilization rate of the enhanced agro-climatic resources is possible by introducing new combinations of cultivars, adopting more laborsaving technologies, and providing incentives to farmers.