In peri-urban smallholder dairy herds, farmers face challenges in drying off cows due to a lack of evidence-based recommendations. This study examined the associations between cow drying-off practices, mean milk yield at drying off and during early successive lactation, and the odds of mastitis and udder leakage cases in herds around Nakuru city, Kenya. A cross-sectional survey of 232 cows across 172 herds was conducted. Mean milk yield was determined using a general linear model, while the odds ratios for mastitis and udder leakage were estimated using a binary logistic regression model, with drying-off practice, cow breed, and dairy management intensification as explanatory variables. All the three explanatory variables were significantly associated (p<0.05) with mean milk yield at drying off, early successive lactation, and the occurrence of mastitis and udder leakages. Cessation of milking (57.3%) was more common than abrupt cessation (42.7%). Mean milk yield was 2.6 liters/day at drying off and 13.4 liters/day during early successive lactation. Teat sealants were applied to cows producing more than 5 liters/day, while gradual reduction in milking, complete cessation of milking, or dry-cow therapy was used for cows producing less than 3 liters/day. During early successive lactation, cows dried off using teat sealant, salt application, stopping concentrate feeding, or gradual reduction in milking produced more milk (14 liters/day) than those dried off by abrupt cessation or dry-cow therapy (10-12 liters/day).Relative to abrupt cessation, the odds of mastitis and udder leakage were lower (p<0.05) with dry-cow therapy (odds ratio 0.12; 0.12), gradual cessation of milking (odds ratio 0.22; 0.29), or stopping concentrate feeding (odds ratio 0.14; 0.26). The study found that gradual reduction in milking (47%) and abrupt cessation of milking (22%) were the most common drying-off practices. These methods are effective for cows producing less than 3 liters/day at the start of drying off and do not result in milk loss during early successive lactation. However, abrupt cessation of milking is more likely to result in poor udder health outcomes. Though teat sealant was rarely used (3.9%), it proved effective for cows producing more than 5 liters/day, maintaining milk production and udder health during early successive lactation. These findings provide crucial insights for farmers on selecting appropriate drying-off practices to optimize milk yield and udder health.