The transition period is a stressful adaptation time for high-producing dairy cows. The inability to meet her energy requirements leads to a state of negative energy balance, often accompanied by increased lipid mobilization from adipose tissue. Body condition scoring (BCS) provides a visual appraisal of lipid mobilization. Our aim was to investigate the association of body condition loss on hepatic and ovarian tissue function in dairy cows during the transition period until onset of breeding. Holstein cows were studied as of 4 weeks pre-calving until 8 weeks post-calving and retrospectively grouped by changes in BCS. Group 1 (n = 9) consisted of cows that lost <0.75 BCS and Group 2 (n = 8) cows that lost ≥0.75 BCS during the sampling period. Cows were subjected to blood collection and liver biopsies at −3 weeks, approximate day of calving and +7 weeks. The last liver biopsy was accompanied by follicular aspiration of the dominant follicle and retrieval of granulosa cells (GC) and follicular fluid. We evaluated levels of circulating metabolic indicators, and hepatocyte and GC mRNA. Circulating levels of β-hydroxybutyric acid, glucose and haptoglobulin used to assess liver and metabolic stress were unchanged between groups. The proportion of nonesterified fatty acids (NEFAs) were assessed by gas chromatography in both follicular fluid and blood samples collected at +7 wk, where linoleic acid was the predominant NEFA, representing 52% of all NEFAs, yet no differences were observed between fluids and groups. Reproductive competence was evaluated through mRNA abundance of genes required for follicular development (FSHR and LRP8) in granulosa cells, but remained constant between groups. In hepatocytes, CYP7A1 transcripts gradually increased (P < 0.05) in Group 2 from −3 wk to +7 wk, but remained constant in Group 1. Other transcripts involved in lipid metabolism and inflammation (LDLR, ACAT1, and IL1B) remained unaltered between groups at all time points. Thus, cows experiencing elevated BCS loss lead to a gradual increase in hepatic CYP7A1, an enzyme involved in bile acid synthesis from cholesterol, suggesting that Group 2 experienced a greater need for cholesterol removal from the body.