Lipoprotein sphingomyelin (SM) is a choline-containing phospholipid. Hepatic steatosis and hyperlipidemia promotes long-chain SM accumulation in liver. Following the hepatic secretion of SM within lipoproteins, circulating SM may be hydrolyzed to increase the insulin antagonist ceramide. Our objective was to characterize changes in bovine lipoprotein SM during the peripartum, and compare lipoprotein SM levels with insulin sensitivity. Twenty-five pregnant, multiparous Holstein dairy cows were enrolled 28 d before expected parturition and fed a diet formulated to meet or exceed nutrient requirements. The hyperinsulinemic-euglycemic clamp procedure was performed to assess insulin action. Blood and liver were collected at d −12 and 10, relative to parturition. Blood was also collected at calving. To isolate TAG-rich, low-density, and high-density lipoproteins (VLDL, LDL, and HDL, respectively), we used fast protein liquid chromatography. Lipoprotein SM were measured using mass spectrometry. Data were analyzed using a mixed model with repeated measures including fixed effect of time and random effect of cow. VLDL total SM and dihydro-SM levels decreased by ~75% from d −12 to parturition (P < 0.01) and remained low through d 10 postpartum. In contrast, LDL total SM decreased 22% from d −12 to 0 then increased 72% by d 10 (P < 0.01). A less pronounced but similar pattern was observed for HDL total SM. Across all lipoprotein classes, C22:0, C22:1, C20:0, and C16:0 SM were the most abundant SM species. All 8 SM and 3 dihydro-SM quantified in VLDL decreased postpartum (P < 0.01); however, species differences were observed for LDL and HDL SM. For example, postpartum elevations in LDL C16:0, C20:0, and C24:0 SM were observed, whereas LDL C24:1 SM decreased (P < 0.01). Interestingly, VLDL total SM was inversely related to liver lipid content (r = −0.59; P < 0.01) and basal fatty acid levels (r = −0.44; P < 0.01). Prepartum and postpartum VLDL total SM were negatively correlated with insulin sensitivity (clamp index; ~r = −0.50; P < 0.05), a response not observed for LDL or HDL total SM. Our results confirm dynamic remodeling of bovine lipoprotein SM during the peripartum. Moreover, changes in VLDL SM relate to steatosis, hyperlipidemia, and insulin sensitivity.