Knowledge about individual daily herbage dry matter (DM) intake (DMI) helps identifying efficient dairy cows and adapting supplementation better to herbage intake and nutrient requirements of grazing dairy cows. With the aid of behavioural characteristics, raw data recorded with the RumiWatch (RW) system and processed with the RW converter 0.7.3.31 (C31), estimation of herbage DMI may be possible. First, C31, which allows differentiation of prehension bites and mastication chews, was validated through direct observation of behavioural characteristics and compared to the previous RW converter 0.7.3.11 (C11). Further, the influence of a low and high pre-grazing herbage mass (HM), with the same target herbage allowance (HA), on bite mass, DMI, number of prehension bites, and milk production was investigated. In total, 24 lactating Holstein cows were pairwise allotted to one of two HM treatments. The cows received a new pasture paddock twice per day with a daily target HA of 22 kg DM per cow/day. On average, low HM (LHM) and high HM (HHM) paddocks had an HM of 589 and 2288 kg DM/ha, respectively, above 6.7 click units (1 CU = 0.5 cm). Overall, LHM cows produced 2.7 kg/day more milk and 2.5 kg/day more energy-corrected milk, had the same herbage DMI and a similar prehension bite mass. The averaged bite mass per week was 0.49 g DM/bite (LHM) or 0.47 g DM/bite (HHM), respectively. A longer eating time (617 vs. 559 min/day) and a shorter rumination time (297 vs. 365 min/day) were observed for the LHM cows compared with the HHM cows. The validation of the RW showed similar results for C11 and C31 apart from prehension bites, where C31 showed a mean absolute deviation of 12.4%. Pre-grazing HM had no effect on relevant behavioural characteristics for prospective intake estimation, namely, bite mass and number of prehension bites.