Abstract: Rapid urbanization has intensified land-use competition, landscape fragmentation, and ecological pressure in urban-rural fringe areas, making it necessary to evaluate how cultivated land maintains production functions under multiple disturbances and to translate the diagnosis into spatially differentiated governance. This study took the urban-rural fringe of the Wuhan Metropolitan Area as the research object. The fringe was delineated by clustering the intensity and spatial fluctuation of nighttime-light data, and 4,775 valid grids of 1 km × 1 km were established as the basic evaluation units. A cultivated land use resilience framework was constructed from resistance, adaptability, and recovery. Resistance described the stability of root-zone soil moisture, crop evapotranspiration, and terrain conditions; adaptability reflected landscape connectivity, market accessibility, construction-land pressure, and production-use stability; and recovery represented the response to extreme drought. Entropy weighting was applied to a pooled two-year sample to calculate comparable resilience scores for 2012 and 2022. Local spatial autocorrelation analysis identified spatial clusters and outliers, geographically weighted regression revealed spatially varying effects, and fuzzy-set qualitative comparative analysis identified county-level configurations associated with high resilience. The results showed that cultivated land use resilience remained generally at a medium-to-high level but declined substantially during 2012–2022. The mean score decreased from 0.79 to 0.65, and the proportion of high-resilience grids fell from 84.67% to 27.50%. High-value areas contracted toward relatively continuous outer-suburban agricultural spaces, whereas low-value clusters expanded around the main urban area, development corridors, and urban expansion fronts. Global Moran’s I decreased from 0.26 to 0.24, indicating that positive spatial autocorrelation persisted while overall clustering weakened slightly. The driving effects were markedly spatially non-stationary. Compared with the global ordinary least squares model, the geographically weighted regression model increased the adjusted coefficient of determination from 0.444 to 0.625 and reduced the corrected Akaike information criterion from 10,755.08 to 9,488.99. Population density and point-of-interest density exerted stronger negative effects in the inner fringe and along the Wuhan–Ezhou–Huangshi development corridor, where construction encroachment and land-use competition were concentrated. In outer-suburban and hilly agricultural areas, precipitation and groundwater depth became more important because direct urban pressure weakened and water availability increasingly constrained crop physiological stability. Surface-water accessibility was significant in the global model but seldom became the strongest local constraint. Proximity to rivers and lakes captured regional differences in potential water availability, whereas its effective contribution to field production was conditioned by plot fragmentation, irrigation and drainage connectivity, and local water-use organization. No single antecedent condition was necessary for high resilience. Eight effective configurations were identified, with an overall solution consistency of 0.9146 and coverage of 0.7021. According to their dominant condition combinations and regional contexts, the configurations were summarized as four modes: water-soil resource endowment, suburban ecological mosaic, social adaptation and feeding-back, and hilly rain-fed conservation. These modes show that high resilience can be maintained through different combinations of development intensity, population pressure, urban location, precipitation, groundwater depth, and surface-water proximity. By integrating resilience level, local spatial association, dominant constraints, and configurational pathways, the study area was divided into core protection, pressure regulation, endowment enhancement, and risk warning zones. The corresponding priorities are to maintain contiguous high-resilience farmland, control construction encroachment and repair fragmented landscapes, improve water conservation and irrigation conditions according to local natural constraints, and establish dynamic monitoring for transitional areas. The findings demonstrate that cultivated land use resilience in urban-rural fringe areas is jointly shaped by spatially differentiated pressures and multiple conditional pathways. Linking grid-scale diagnosis with county-level implementation can improve the territorial precision and practical operability of cultivated land protection.