In this study, cow reticulorumen content pH and temperature together with the activity were registered using smaXtec boluses, specially designed for animal care. Body weight, rumination time, milk fat/protein ratio, milk yield, milk lactose, milk electrical conductivity, milk somatic cell count and consumption of concentrated feed were registered by Lely Astronaut® A3 milking robots. The cows in this study were assigned into two groups according to the milk lactose concentration: group 1—milk lactose < 4.70% (n = 20), group 2—milk lactose ≥ 4.70% (n = 15). The following cows were further classified according to milk fat and protein ratio: F/P < 1.2 (class 1), F/P = 1.2 (class 2) and F/P > 1.2 (class 3). According to our results, we can conclude that inline registered milk lactose concentration can be used to indicate the health status and reproductive success of fresh dairy cows. Cows with an increased lactose concentration (≥4.70%) showed more activity (54.47%) and had less risk of mastitis (determined by lower milk electrical conductivity (EC) and somatic cell counts (SCC)) and metabolic disorders, determined by milk F/P. A higher glucose concentration was also apparent in the cows with higher lactose concentration. Registered lower levels of milk lactose can be used for early identification of metabolic disorders and mastitis (set at milk SCC ≥ 100 thousand/mL). Lactose levels in cows’ milk were positively associated with their reproductive success.