Exploring cultivated land use and conservation from a resilience perspective is crucial to address regional food security concerns. This article first examines the theoretical applicability of resilience in the context of cultivated land use systems and subsequently introduces a specific concept of cultivated land system resilience (CLSR). Focusing on the middle reaches of the Yangtze River, a major grain‐producing area in China, the study constructs a measurement system that encompasses five dimensions: endowment of production, socioeconomic factors, scale structure, ecological pressure, and food security. This system is used to evaluate the spatio‐temporal evolution and influencing mechanisms of CLSR in the region from 2001 to 2020. The results indicate that the level of CLSR increased by 7.2% overall and exhibits a distinct spatial pattern, with high‐value areas expanding from the center to the surrounding regions. Furthermore, CLSR shows a positive spatial correlation with rising levels of agglomeration. The spatial heterogeneity of CLSR is influenced by the interaction of various factors, resulting in a partially nonlinear two‐factor enhancement. The influence of each factor varies between different time periods, shifting from ecological pressure to scale structure, ultimately affecting food security. Thus, the resilience perspective offers greater explanatory power to identify key vulnerabilities in the regional cropland system. This approach can improve the efficient allocation of cropland resources and promote sustainable and healthy development at the regional level.