Ceramide mediates insulin resistance in obese diabetics. In dairy cattle, the transition from gestation to lactation is characterized by the accrual of ceramide in liver, skeletal muscle, and circulation. Current evidence suggests that the de novo synthesis of ceramide from saturated fatty acids contributes to hepatic ceramide synthesis; however, sphingomyelin (SM) hydrolysis may also contribute to ceramide supply. Our objective was to characterize changes in hepatic SM during the peripartum in dairy cattle. Twenty-five pregnant, multiparous lean (BCS 3.0 ± 0.2) or overconditioned (OVER; BCS 3.9 ± 0.3) Holstein cows were enrolled 28 d before expected parturition. Blood samples were routinely collected. Liver biopsies and the hyperinsulinemic-euglycemic clamp were performed 2 wk before and after parturition. Sphingolipids were quantified using mass spectrometry. Data were analyzed using a mixed model with repeated measures. Similar to hepatic ceramides, C24:0 and C22:0 SM were the most abundant SM species. Although adiposity and time did not modify total SM levels, the hepatic concentrations of C16:0, C18:0, and C20:0 SM increased with time (P < 0.01). In contrast, hepatic C24:0, C24:1, and C26:0 decreased postpartum (P < 0.01). Total dihydro-SM (DHSM) increased with time (P < 0.01); albeit, C16:0, C24:0, and C26:0 DHSM decreased after parturition (P < 0.01). Hepatic C18:0 and C20:0 SM, and C20:0 DHSM levels were greater in OVER (P < 0.01), relative to lean. In contrast, very long-chain C26:0 and C26:1 SM, and C26:1 DHSM were lower in OVER (P < 0.05), relative to lean. Hepatic total DHSM and individual SM were positively correlated with liver lipid content (e.g., C16:0, C18:0, C20:0; P < 0.01), whereas C26:0 SM and DHSM were inversely associated with steatosis (P < 0.01). Similar relationships were observed between hepatic SM and circulating fatty acids. Prepartum, long-chain SM were positively associated with insulin sensitivity (clamp index; P < 0.05), whereas very long-chain SM were negatively related to insulin action (P < 0.05). The observed reciprocal response between long-chain and very long-chain SM mirror peripartal changes in hepatic and plasma ceramide.