Abstract: Using wheat yield data from 407 county-level administrative units in Hebei, Jiangsu, Anhui, Shandong, and Henan provinces over the period 1985–2019, together with relevant provincial-level statistical data, this study employs the mixture distribution model, the standard attribution model, the spatial autoregressive model, and the SinoTERM multi-regional computable general equilibrium model to examine the effects of agricultural insurance on wheat yield resilience, the underlying pathways, and the associated macroeconomic effects. The main findings are as follows. First, the effect of agricultural insurance on wheat yield resilience exhibits a significant inverted U-shaped pattern. At relatively low levels of insurance development, the wealth effect predominates and enhances wheat yield resilience; as the level of insurance development rises, the risk substitution effect gradually emerges and may eventually suppress wheat yield resilience. Nevertheless, the average marginal effect over the sample period remains positive. Second, the pathway analysis indicates that agricultural insurance affects wheat yield resilience primarily by altering the rate of technological progress in the low-yield component, while its effect on the high-yield component is statistically insignificant. Quantile regression results further indicate that the effect of agricultural insurance is more pronounced in counties with low levels of resilience, whereas no statistically significant effect is observed in counties with high levels of resilience. Third, simulations using the SinoTERM model show that, under both the “targeted implementation in the five provinces” scenario and the “nationwide extrapolation” scenario, land-efficiency shocks calibrated on the basis of the positive average effect estimated for the sample increase wheat output, household wheat consumption, and wheat exports, while reducing wheat prices. At the macroeconomic level, the simulations indicate a modest increase in real output accompanied by a modest decline in the overall price level. These findings provide empirical evidence for optimizing agricultural insurance policies in a phased and differentiated manner and for strengthening the resilience of the food production system.