Our objective was to determine the impact of abomasal infusion of increasing doses of oleic acid (OA; cis-9 C18:1) on fatty acid (FA) digestibility and production responses of lactating dairy cows. Eight rumen-cannulated multiparous Holstein cows (138 ± 71 DIM) were randomly assigned to treatment sequence in a replicated 4 × 4 Latin square design with 18-d periods consisting of 7 d of washout and 11 d of infusion. Animals received the same diet, which contained (%DM) 27.8% NDF, 17.0% CP, 27% starch, and 3.3% FA (1.8% DM from a saturated FA supplement containing 31% C16:0 and 54% C18:0). Treatments were 0, 20, 40, or 60 g/d of OA delivered at 6-h intervals. Production and digestibility data were collected during the last 4 d of each infusion period. The statistical model contained the random effect of cow within square and the fixed effects of period, treatment, and their interaction. Results in the text are presented in the following order: 0, 20, 40, and 60 g/d. OA infusion did not affect dry matter intake (P = 0.31) or NDF digestibility (P = 0.54). OA linearly increased digestibility of total FA (61.1, 66.7, 65.8, and 67.4; P < 0.01), 16-carbon FA (60.4, 66.7, 66.4, and 68.0; P < 0.01), and 18-carbon FA (61.3, 66.7, 65.5, and 67.1; P < 0.01). Therefore, OA linearly increased absorbed total FA (638, 705, 681, and 724; P = 0.04), 16-carbon FA (141, 157, 153, and 163; P = 0.02), and 18-carbon FA (457, 504, 484, and 516; P = 0.05). OA tended to linearly increase milk yield (P = 0.09), 3.5% fat-corrected milk (P = 0.08), and energy-corrected milk (P = 0.09). OA did not affect milk fat yield but tended to increase milk fat concentration (3.35, 3.36, 3.42, and 3.21%; quadratic P = 0.06). OA did not affect the yield of de novo or mixed milk FA but linearly increased yield of preformed FA (578, 587, 599, and 623 g/d; P = 0.04), predominantly through increased yield of OA (linear P < 0.01). OA also tended to linearly increase C4:0 yield (P = 0.09) in milk. OA increased plasma insulin concentration from 0.80 mg/L to 0.98 mg/L, but did not differ by dose (P < 0.01). In conclusion, OA infusion increased FA digestibility, preformed milk FA yield, and circulating insulin without negatively affecting dry matter intake.