The objective was to compare differences in reproductive performance for dairy cows grouped based on the combination of data for predictors available during the prepartum period and before the end of the VWP, automated estrus alerts (AEA) during the VWP, and the combination of both factors. In a cohort study, data for AEA and potential predictors of the percentage of cows inseminated in estrus (AIE) and pregnancies per AI (P/AI) for first service, and the percentage of cows pregnant by 150 DIM (P150) were collected from -21 to 49 DIM for lactating Holstein cows (n=886). The association between each reproductive outcome with calving season (cool, warm), calving-related events (yes, no), genomic daughter pregnancy rate (gDPR; high, medium, low), days in the close-up pen (ideal, not ideal), health disorder events (yes, no), rumination time (high or low CV prepartum and high or low increase rate postpartum), and milk yield (MY) by 49 DIM (high, medium, low) were evaluated in univariable and multivariable logistic regression models. Individual predictors (health disorders, gDPR, and MY) associated with the three reproductive outcomes in all models were used to group cows based on risk factors (RF; yes, n=535 or no, n=351) for poor reproductive performance. Specifically, cows were included in the RF group if any of the following conditions were met: the cow was in the high MY group, had low gDPR, or had at least one health disorder recorded. Cows were grouped into estrus groups during the VWP based on records of AEA (E-VWP, n=476 or NE-VWP, n=410). Finally, based on the combination of levels of AEA and RF cows were grouped into an estrus and no RF (E-NoRF, n=217), no estrus and RF (NE-RF, n=276), no estrus and no RF (NE-NoRF, n=134), and estrus and RF (E-RF, n=259) groups. Cows received AIE up to 31 d after the end of the VWP, and if not AIE, received timed AI after an Ovsynch plus progesterone protocol. Logistic and Cox proportional hazard regression compared differences in reproductive outcomes for different grouping strategies. The NoRF (AIE:76.9%; P/AIE:53.1%; P150:84.5%) and E-VWP (AIE:86.8%; P/AIE:44.8%; P150:82.3%) groups had more cows AIE, P/AI, and P150 than the RF (AIE:64.5%; P/AIE:34.9%; P150:72.9%) and NE-VWP (AIE:50.0%; P/AIE:38.9%; P150:72.1%) groups, respectively. When both factors were combined, the largest and most consistent differences were between the E-NoRF (AIE:91.3%; P/AIE:58.7%; P150:88.5%) and NE-RF groups (AIE:47.3%; P/AIE:35.8%; P150:69.5%). Compared with the whole population of cows or cows grouped based on a single factor, the E-NoRF and NE-RF groups had the largest and most consistent differences with the whole cow cohort. The E-NoRF and NE-RF group also had statistically significant differences of a large magnitude when compared with the remaining cow cohort after removal of the respective group. We conclude that combining data for AEA during the VWP with other predictors of reproductive performance could be used to identify groups of cows with larger differences in expected reproductive performance than if AEA and the predictors are used alone.