Identifying cows that are at greater risk for disease prior to calving would be a valuable addition to transition management. Prior to the commercial release of software features in an automated behavioral monitoring system, designed to identify cows in the dry period at greater risk of disease postpartum, a retrospective analysis was carried out in five dairy herds to evaluate whether the software could identify prepartum cows that subsequently received health treatments postpartum and whether prepartum alerts (transition alerts) are associated with a reduction in milk production in the subsequent lactation. Herd management and production records were analyzed for cows receiving treatment in the first 21 d of lactation (days in milk, DIM) for clinical mastitis, reproductive tract disease (metritis, retained fetal membranes), metabolic disease (hypocalcemia, ketosis and displaced abomasum) and for cows exiting the herd by 60 DIM. Data was gathered for 986 cows, 382 (38.7%) of which received a transition alert and 604 (61.3%) that did not. During the first 21 DIM 312 (31.6%) cows went on to receive a disease treatment, of these 51.9% (n = 162/312) were transition alert cows and 48.1% (n = 150/312) non-transition alert cows, while 8.6% (n = 33/382) alert cows exited the herd by 60 DIM compared to 4.8% (n = 29/604) of cows that did not receive an alert. A cow receiving a transition alert (OR = 1.76, 95% confidence interval (CI) = 1.27-2.44) and increasing parity (OR = 2.03, 95% CI = 1.44-2.86) were both associated with increased risk of receiving a disease treatment in the first 21 DIM. The occurrence of a transition alert was negatively associated with both week 4 milk yield (daily average yield in fourth week of lactation) and predicted 305 d yield. Transition alerts correctly predicted 62.5% (95% CI: 59.3-65.5) of treatments with a sensitivity of 42.4% (95% CI: 37.4-45.5) and a specificity of 75.2% (95% CI: 71.5-78.6). Associations were identified between postpartum health and production outcomes and prepartum behavioral measures from an automated activity monitoring system.