It is well established in the literature that feeding free vegetable oils rich in oleic acid results in greater milk fat secretion than does feeding linoleic-rich oils. The objectives of these experiments were to analyze the effects of oleic and linoleic acid when fed in the form of full-fat soybeans and the interaction between soybean particle size and fatty acid (FA) profile. Soybeans were included in diets on an iso-ether extract basis and diets were balanced for crude protein using soybean meal. Experiment 1 used 63 cows (28 primiparous, PP; 35 multiparous, MP) housed in a freestall barn with Insentec roughage intake control gates (Marknesse, the Netherlands). Cows were divided into 4 mixed parity groups within the same pen. Two groups were assigned to each of the 2 diets: whole raw Plenish (WP, high oleic; Dupont-Pioneer, Johnston, IA) soybeans or whole raw conventional (WC, high linoleic) soybeans. The MP cows exhibited significantly increased milk fat yield on the WP diet compared with the WC diet. A significantly greater C18 milk FA yield by the MP cows fed WP was observed compared with those fed WC, but no difference was present in the C16 or short-chain FA yield. No effects were seen in the PP cows. Experiment 2 used 20 cows (10 PP, 10 MP) in 2 balanced 5 × 5 Latin squares within parity. Cows received 5 diets: raw WP and WC diets, raw ground Plenish and conventional soybean diets (GP and GC, respectively), and a low fat control. A significant benefit was found for the GP diet compared with the GC diet for milk fat concentration and yield. In experiment 2, no difference was observed between cows fed the WP compared with the WC diet. In experiment 2, cows consuming the Plenish diets produced less milk than when consuming the conventional soybean diets. The soybean diets resulted in significantly more C18 and less <C18 FA compared with the low fat diet. The GP diet resulted in significantly more C18 FA than the GC diet and the ground soybeans resulted in less C16 FA compared with whole soybeans. In both experiments, cows fed the Plenish diets exhibited decreased trans-10 18:1, a FA often increased during milk fat depression, compared with those fed the conventional soybean diets, though differences were not observed in trans-10,cis-12 conjugated linoleic acid.