Relationships among dietary roasted whole soybeans (RSB), milk fatty acid profile, and the development of spontaneous oxidized flavor of milk were investigated by using 20 commercial dairy herds. Diets contained 0 to 15.3% of dry matter as RSB. Concentrations of dietary RSB were correlated positively with concentrations of C18:2 and C18:3 in milk fat. Concentrations of alpha-tocopherol, beta-carotene, and ascorbic acid in milk decreased from 0 to 3 d of storage (4 degrees C), and oxidized flavor in milk increased linearly between 0 and 8 d of storage. Milk fatty acid profile did not change during storage. The development of oxidized flavor at 8 d postsampling was correlated (r) with increased concentrations in milk fat of C18:2 (0.49), C18:3 (0.55), total polyunsaturated milk fatty acids (0.50), and dietary concentrations of RSB (0.38). Multiple regression was used to quantify relationships between variables and oxidized flavor (samples stored 8 d). All significant models included milk concentrations of Cu and dehydroascorbic acid. Concentrations of C18:2, C18:3, or total polyunsaturated fatty acids in milk fat, or dietary RSB concentrations, and interactions of those variables with Cu were included in individual models. Milk with high concentrations of polyunsaturated fatty acids and Cu were most susceptible to oxidation. Feeding RSB increased polyunsaturated fatty acid concentrations in milk fat, which increased the likelihood of oxidized flavor, especially when milk had high concentrations of Cu.