Obesity promotes hepatic steatosis via (1) enhanced fatty acid (FA) uptake and triacylglycerol (TAG) esterification, (2) increased partitioning of FA toward the synthesis of lipid mediators of metabolic disease such as ceramide and diacylglycerol (DAG), and (3) the inflammation-driven degradation of sphingomyelin (SM) and phosphatidylcholine (PC), which may compromise lipoprotein secretion. We aimed to determine whether elevated prepartum adiposity predisposes dairy cows to a modified hepatic lipidome reflecting metabolic impairment during the peripartum. Lean (BCS 3.0 ± 0.2; n = 13) and overconditioned (OVER; BCS 3.9 ± 0.3; n = 12) Holstein dairy cows were enrolled −28 d, and liver tissue was biopsied at d −12 and 10, relative to parturition. Untargeted lipidomics was performed using quadrupole time-of-flight mass spectrometry. Multivariate analysis of normalized, auto-scaled lipids included ANOVA and Pearson correlation coefficient procedures. Lipidomics revealed 406 hepatic lipids including 83 TAG, 106 monoalkyl-diacylglycerols (MADAG), 22 DAG, 32 ceramides, 30 SM, 33 PC, and 41 phosphatidylethanolamines (PE). Elevated postpartum plasma FA levels were accompanied by increased liver lipid content (7 versus 11%; P < 0.05) and plasma β-hydroxybutyrate (430 versus 506 μM; P < 0.01) in OVER. Omics revealed 98 complex lipids affected by adiposity (P < 0.05). Relative to lean, OVER displayed elevations in TAG, MADAG, DAG, and select ceramides, while showing stronger reductions in PC postpartum (P < 0.05). A total of 13 PC decreased in OVER, relative to lean (e.g., PC 36:6; P < 0.05). Several SM were lower in OVER (e.g., SM 40:3; P < 0.05), although the changes were not uniform across all SM moieties (e.g., SM 46:1 increased in OVER; P < 0.05). Total ceramides were positively correlated with total DAG and TAG (FDR <0.01) but inversely related to select PC and SM (FDR <0.01). Prepartum adiposity remodels the postpartum hepatic lipidome. Future research will need to determine whether the peripartal depletion of hepatic PC predisposes overconditioned cows to impaired lipoprotein secretion and fatty liver disease.