The objective of this study was to characterize the associations between body condition score (BCS) and BCS change (∆BCS), determined by an automated camera system during early lactation and close to artificial insemination (AI), and the subsequent pregnancy loss (PL) in Holstein cows. A secondary objective was to determine the impact of disease on PL, considering multiple time periods relative to AI. Data from 9,430 lactations in 6,884 Holstein cows in a commercial dairy operation located in Colorado, USA were included in this retrospective observational study. Cows were subject to first AI at about 80 DIM (primiparous) and 60 DIM (multiparous), following a double OvSynch protocol. Pregnancy diagnosis was performed via transrectal ultrasonography on day 32 ± 3 after AI and reconfirmed on day 80 ± 3 after AI. Cameras mounted on the sorting gate at each exit (n = 2) of the milking parlor generated BCS on a five-point scale with 0.1 increments. The BCS at calving (BCS1), 21 DIM (BCS21), 56 DIM (BCS56), AI resulting in pregnancy (BCSAI), and 90 d post AI (BCSAI90) were selected for the analyses and subsequently categorized as low (≤ lower quartile), moderate (interquartile range), and high (≥ upper quartile). Changes in BCS were calculated by periods of interest as change from calving to 21 DIM; change from calving to 56 DIM; change from 56 DIM to AI; and change from AI to 90 d post AI and assigned into categories to facilitate the analysis. Data were examined using logistic regression, considering parity category, season at calving and AI, DIM at AI, milk yield up to 60 DIM, and occurrence of disease as covariables. The logistic regression analyses indicated that the odds of PL were greater in cows in the low BCS category relative to cows in the high BCS category at 56 DIM (OR 95% CI = 1.41 [1.12-1.79]), AI (1.31 [1.05-1.65]), and 90 d post AI (1.38 [1.10-1.74]). Likewise, cows with large loss in BCS between calving and 21 DIM (1.46 [1.10-1.94]) and loss in BCS between AI and 90 d post AI (1.44 [1.15-1.81]) had greater odds of PL compared with cows with no loss of BCS within the same period. Occurrence of disease at all the time periods considered in the analysis had a consistent detrimental impact on maintenance of the pregnancy, supporting the concept that pre and postconceptional disease affects embryonic survival. Overall, low BCS, more pronounced reductions in BCS occurring closer to AI, and occurrence of disease resulted in greater PL in this Holstein population.