The objective was to assess the association between colostrum and plasma insulin concentration around parturition on milk yield in Holstein dairy cows. Our hypothesis was that low plasma insulin concentration (PI) around calving and during early lactation, as well as high insulin concentration in colostrum would be associated with milk production. Two experiments were conducted. In experiment 1, blood samples (BS) from cows (n = 48) were collected at −7, 0, 3 and 7 d relative to the day of parturition. Additionally, colostrum samples were collected immediately after calving. In experiment 2, BS from primiparous and multiparous cows (n = 237) were collected at 0, 3 and 7 d relative to the day of parturition. Insulin was measured using a bovine ELISA kit. Weekly milk yields were recorded for the first 7 weeks after calving. In experiment 1, cows were grouped according to the PI at d 0 based on the median (0.42 ng/mL), into LOW (PI < 0.42 ng/mL, n = 23) and HIGH (PI > 0.41 ng/mL, n = 25) cows. Insulin concentration at −7, 3 and 7 d did not differ between groups. However, LOW cows had significantly lower PI at d 0 (LOW, 0.28 ± 0.07; HIGH, 0.71 ± 0.06) compared with HIGH cows. No differences were found in colostrum insulin concentrations between groups. Relative to HIGH cows, LOW cows produced 5 kg/d more milk (LOW, 42 ± 1.15; HIGH, 37 ± 1.34). In experiment 2, cows were grouped according to the PI levels at d 0 in quartiles (1stQ, PI <0.29 ng/mL, n = 57; 2ndQ, 0.29 ng/mL ≤ PI ≤ 0.34 ng/mL, n = 60; 3rdQ, 0.34 ng/mL < PI ≤0.43 ng/mL, n = 58; 4thQ, PI > 0.43 ng/mL, n = 62). Primiparous cows in the 4thQ had significantly higher PI at d 0, and produced significantly less milk (1stQ, 32.1 ± 2.4; 2ndQ, 33.6 ± 1.6; 3rdQ, 35 ± 1.4; 4thQ, 29.5 ± 1.1) compared with cows in the other quartiles. Multiparous cows in the 4thQ had significantly higher PI at d 0 compared with cows in the other quartiles. Additionally, cows in the 1stQ produced ~5 kg/d more milk (1stQ, 47.6 ± 1.2; 2ndQ, 42.8 ± 1.3; 3rdQ, 42.5 ± 1.4; 4thQ, 41.3 ± 1.7) compared with cows in the other quartiles. PI at 3 and 7 d among the quartiles did not differ between groups. We conclude that low plasma insulin concentration at the day of parturition seems to be critical for milk yield in the long term.